June 23, 2017

20+ Experts Reveal Fun and Interesting Questions To Ask Him on a First Date


“I define connection as the energy that exists between people when they feel seen, heard, and valued; when they can give and receive without judgment; and when they derive sustenance and strength from the relationship."

~ Brené Brown

# 1. Purpose, Passion and Vulnerability

1. What's your primary dating purpose?

In other words, why are you dating? This question is actually best asked before the first date, to save time, resources, energy, and emotional angst.

Make it clear what your goal is -- Are you looking to broaden your social circle? Is a casual, romantic encounter what you're comfortable with, and all you can really handle at the moment? Are you on-go for marriage, kids, diapers and baby wipes?

Spend your time and your energy wisely, by clarifying these questions for yourself and for each of the people you're considering meeting.

2. What makes you happy, brings you joy, makes you smile?

What are you most passionate about? What makes you tick? The trick is to ask these questions without attachment to the response. You'll be drawn in, interested, engaged and enthused or ... you won't.

Either way, it's good to know if you're in natural alignment with this person's interests, joys and passions...or not.

If not, make a friend, be warm, kind, and pleasant, look for ways to bring a smile to this person's face, and know that your journey toward partnership is still in process.

3. What would you love to know about me?

Ask me anything. What question have you always wanted to ask on a first date, but never have? What question usually doesn't get asked till Date Number Five, that you would love to know the answer to now?

Dating is most enjoyable when it's an adventure. Dare to be vulnerable, dare to encourage vulnerability on the other side of that table, and watch what happens.

Julie Ferman, Matchmaker and Dating Coach – www.julieferman.com

# 2. Explore his core values, commitment and happiness

Most of us consider first dates as scary or exciting, but we rarely think of them as portals to data about a potential lover or mate. That’s because we’re usually so worried about what our date will think of us, that we forget that these initial moments together can yield a wealth of information about a possible future with this person.

Once we view first dates as a time to tactically get to know someone, we need to be armed with strategic questions to discern if we will wish to go out with this person again.

Here are three questions to consider.

You may not wish to ask them outright—after all, you don’t want your date to feel as if it’s job interview—but you will want to slip them into conversation and find out their answers.

1. What are your date’s core values?

Many people look primarily at their attraction to someone, his intelligence and professional drive, or particular personality traits such as kindness and generosity. While these often do tell you something about a individual’s core values, they may tell you all you need to know.

It’s fine on a first date to ask, “What’s most important to you in life?” or “What value do you cherish above all else?” These are thoughtful questions and put you in a light of being a interested person. Of course, you may be asked the same question in return and need to be ready with answers of your own.

Values, whether political, lifestyle, religious or whatever are important when you’re looking for a good match. If you’re a devout Evangelical and your date is an Atheist, that’s important to know right off the bat because it may be a deal-breaker. Likewise, if you’re a staunch progressive politically and your date is a Tea Party supporter, you may not have enough common ground between you to make a go of it.

2. What are your date’s ideas about romantic commitment?

Many women are afraid to fish for how their date may feel about romantic commitment for fear of seeming too pushy or needy. However, this is an important issue to get a sense of. You don’t want to be going home all dreamy about someone, if all this someone is interested in is dating as many women as he can. Getting involved in these kinds of relationships is a waste of time and energy unless you too are looking to play the field.

One way to ascertain someone’s inclination toward commitment is by asking about previous relationships and, in a general sense, how they went. You could talk about yours and see what happens or ask directly.

Another way is to ask someone what they see themselves doing in a year or five years and listen for any hint that a life partner is in the description you’re hearing if that’s what you want. If you ask directly and your date seems put off or shocked that you’re asking such a question on a first date, that too gives you information about his long-term partnership preferences.

3. Are you happy with your life right now?

Asking about someone’s happiness opens the door to getting to know a date in several ways. First, there’s the direct response given: happy, not so happy, or pretty miserable. But, more than that, the answer to your question may give you a sense of what makes your date happy—going to the track every spare minute or long walks on the beach, having a great work/play balance or beating out the workplace competition.

This question also can start a conversation on what has brought each of you happiness in the past and what might bring more in the future (that is, marriage? children? travel?). It’s also a way to sit back and watch how your date responds to the question: looking happy while talking about pleasurable pastimes or speaking about enjoying work but not looking very happy. If someone is happy hiking and camping out and you’re strictly a high-end hotel kind of gal (or vice versa), you might have a potential compatibility issue.

It bears worth repeating that you are on this date not only to put your best foot forward, but to find out as much about someone as you can in a short period of time. Some of that means asking the right questions. But, it also means being a discerning listener and noticing everything your date does because sometimes you can learn more about people from what they do than from what they say.

Karen R. Koenig, LCSW, M.Ed. – www.karenrkoenig.com

# 3. Keep it casual and light

Throughout my career I have worked with many single women who are looking to find a companion. When someone is actively looking to find someone; they may be going on a lot of first dates. I have been told that the process can become overwhelming and feel like work. While first dates can be exciting, they can also be exhausting and anxiety provoking wondering what to talk about or not talk about.

Keep it casual and light on the first date.

Try not to put so much pressure on yourself or your date. Try and see if you have any common interests and if this person could be a candidate for a second date rather than attempting to figure out if he will end up becoming your husband.

Ask about his career. Is he passionate about it or is it just a job that pays the bills? Talk about what you do for a living and if it is important to you and/ or are either of you working towards a different career or advancement in your current one?

If family is important to you ask about his family.

Does he have siblings?

Are they geographically close?

This is not the time to pry about what kind of relationship he has with his family. Again keep it light and casual. If more information is volunteered by your date, just listen and show interest. Do not make judgements or give your personal opinion about what he is doing with his life or his relationship with his family ( unless you want to scare him off!).

Lastly I would ask what his hobbies are and how he likes to spend his time when he is not at work.

Does he socialize with friends?

Is he a hiker or a runner?

I would share what you like to do as well. If you are interested in similar things and the conversation is easily flowing; perhaps you could chose one of these activities for a second date.

If he is interested in activities that you haven't tried, maybe you would eventually try something new and like it. It doesn't have to mean that you are not compatible if you have different interests. If you do end up in a relationship; make sure you make time for what is important to you while also making time to nurture the relationship.

Remember you don't have to decide on the first date if he is the one. Good luck and have fun!

Trisha Swinton, LPC, LMFT – www.trishaswintoncounseling.com

# 4. Try asking work related questions

These 3 work related questions are not just about work, but open up windows into learning more about him. The idea is they seem less invasive on the outside, but give you more bang for your buck.

1. What is something your boss does that really pisses you off?

This is a fun twist on “what are your pet peeves?” When people ask me about pet peeves a usually response is, “I don’t know… uhhh…uhhh…” and the person might come up with something but often it is lacking.

This more specific question about your date’s boss might be helpful because even if he has a good relationship with his boss usually there is something about that person that gets under his skin so you’ll really see a passionate response which is what you’re looking for… what makes him tick? What is he passionate about?

2. What is the hardest thing about your job?

This is a good way to ask about your date’s weaknesses.

Is it dealing with others on the job?

The amount of work?

Certain types of work?

This question could give you a lot of insight about his struggles in life and tell you more about him.

3. What is your favorite thing to do to unwind from a long day at work?

Chances are you will see your partner most at the end of the day during the week if you both have “normal” working hours so finding out what those evenings will likely look like is a good idea.

Will there be a sports game on TV?

Will it be something outside?

Will it be a project of sorts?

Is alcohol usually involved?

This helps paint a picture on what an ideal evening would look like for your man if you end up getting married and into the grind together. Is this ideal evening something that you could join? Something that allows you to do your own thing? Or would it drive you crazy?

Stacey Steinmiller, LCSW – www.ascounseling.com

# 5. Start by asking some basic questions

A first date can come with feelings of excitement yet some jitters of wondering what the two of you will discuss. It’s a good idea to be prepared to ask some questions to break the ice and to begin a comfortable conversation. The questions may vary depending on the age group and if you already know something about him.

Whether you were introduced by friends, met online, or through a dating service, that first date comes with some trepidation and can feel like an interview, yet it’s a part of the process. While you may already have a little insight into your guy, you will want to know more.

In the initial phase of your date, perhaps you could ask some basic general questions such as:

1. Where are you originally from?

2. What type of occupation are you in?

3. Where did you go to college and what did you major in?

These starter questions lay the foundation of his roots and add an element of who he is. Once you get past the initial general questions, make a mental note and on how elaborate he is with his answers and if he asks you questions as well. It should be a mutually expansive conversation.

You can continue your conversation with getting more information about what he likes regarding hobbies, sports, interests, music, travel, and leisure time.

You may want to add some additional conversation questions:

4. Do you have siblings and where do they live?

5. Do you have any pets?

6. If you could travel anywhere in the world, where would it be?

You can always turn the question into a “tell me about.....” So it doesn’t seem like you are grilling him. Regardless of what happens next, it is a learning experience and it is usually nice to meet someone new.

Connie Clancy Fisher, ED.D. – www.connieclancyfisher.com

# 6. Explore something fun, meaningful and common interests

First dates can cause a natural physiological fear response within the body that can make it difficult to speak, let alone create cohesive sentences, to say to your equally-as-anxious counterpart. Luckily, taking some time to craft a useful line of questioning before your rendezvous can help to reduce those inevitable and uncomfortable queasy sensations felt within the pit of your stomach. Feeling at ease during a first date can also help to build a genuine connection that might just lead somewhere in the future, so it’s best to be prepared!

Let’s consider three main categories of questions to ask your date: something fun, something meaningful, and something connected to your common interests.

1. Something fun

The first date shouldn’t feel like a job interview or interrogation. Inject some fun into the experience by starting with a light or humorous question to break the ice. In order to feel more natural, ensure you keep in line with your own style of humour rather than trying to be a comedian. The goal is to find out more information about your potential match by asking something fun or quirky.

Here are some examples:

If you could choose one superpower, what would it be and why?

What’s the most embarrassing thing you have said on a previous date?

What’s the worst first date you’ve ever been on? Was there a second date?

What quirky questions can you come up with to help ease the anxiety across the table?

2. Something meaningful

Hopefully that awkward first-date feeling has subsided by now, and you can feel more comfortable asking deeper and more significant questions. Being able to communicate effectively is one of the cornerstones of any relationship (intimate or friendly), so it can be important to gauge your potential partner on how they respond to a more meaningful question. What would you like to know more about so that you can have a better understanding of the values, beliefs or goals of your date?

Here are some examples:

What’s the best advice anyone has given you, and have you taken it?

Who has been the biggest influence in your life so far, and how have they changed your path in life so far?

What goals have you set for yourself in the next 1, 3 and 5 years?

What other meaningful questions would you like to know about your date?

3. Something connected to your common interests

You may have met each other randomly one day while waiting at the checkout line at the local grocery store, but chances are, you probably met online. Meeting your potential mate over the internet has become even easier with the multitude of dating applications and websites that help you meet someone who (hopefully) matches your life goals and interests. You may have an idea of your dates interests from their online profile, or from chatting with them in line at the checkout, but finding out more about your potential compatibility with them can be helpful to explore on the first date. This can be accomplished by asking questions around your common interests.

Some examples are:

What is the one thing you are most passionate about in your life right now?

What are the 5 most important things to you in this world?

If you could travel anywhere in the world right now, where would it be and why?

What else might you like to know that connects you and your dates interests?

Hopefully, by the conclusion of the first date, you will know more about what makes him laugh, a meaningful piece of information about who he is, and have an idea about your compatibility with each other. Remember to be yourself, and have fun!

Heather LeGuilloux, MA, RCC - www.heatherleguilloux.ca

# 7. Consider the below 3 questions

Here are a few questions I’d recommend asking a guy on a first date.

1. How are you?

When brainstorming the best questions to ask on a first date, I kept coming up with elaborate questions, and my mind would pull me back to the simple question of “how are you?”

Simple, yes, but powerful. We are typically so consumed with ourselves on a first date. How we look, what they might think of us, if we’re going to like them, etc. Rarely do we think about actually connecting with the other person sitting in front of us.

So take a moment, first, to ask, “how are you?” Ask with sincerity and kindness. Most importantly, be present and take the time to listen.

2. What is your favorite place in the world?

I love this question because not only is it thought provoking, but it gives a lot of insight into a person. It could tell you if they’re a homebody, if they love to travel, what kind of vacations they enjoy. I’m a lover of travel, so having a partner who’s adventurous is important to me. If it’s not that important to you, you could swap it with “What’s your favorite hobby?” or “What do you like to do on the weekends?”

3. What is your biggest goal right now?

This is a great question to find out more about someone’s values. If their goal is fitness related, it shows you that they care about their personal health. If their goal is work related, it shows you that their career is important to them. Depending on how they answer this question, you can follow it up by asking more about why this is so important to them. For example, “Wow, it sounds like you really love your job. What do you love most about it?”

Alexis Meads, MA - www.alexismeads.com

# 8. Be open and authentic

Going on a first date can seem daunting enough without the added pressure of trying to figure out what to talk about. Should you keep it simple and superficial? Should you share some of your secrets? Should be you authentic while still maintaining your boundaries? These are valid questions many women ask themselves while preparing for a first date.

First dates can be fun though and they can be a great place to learn a lot about someone without having them even realize you are fishing for information. Below are three questions you can drop on a first date, when timely appropriately, that will give you enough information to help you decide if a second date is warranted or not.

Each of these questions is designed to help you learn about someone through asking about other areas of their lives.

1. What is your most prized possession?

- This is probably the easiest question to ask someone on a first date. It seems innocuous enough but it’s actually a loaded question. Their answer may reveal a lot about themselves. If they tell you their most prized possession is their video game system, you may have an immature person in front of you. If their most prized possession is a watch their grandfather gave them, it might indicate they are family-oriented and sentimental.

2. Where do you see yourself in five years?

- This is another great question that is seen as a typical first date question so the other person won’t be too shy to share their answer. Even though this is a traditional question to ask, it’s one of the most important questions you can ask. It will let you know if the other person is thinking long-term. It will let you know if they are considering making a career move, buying a house, getting married or going on a 6-month back packing trip through Europe.

You can look at their answer and see if it aligns with your 5-year plan. If he plans to move back home to another state in a year that might not be something you want to start up.

3. What is your relationship like with your mother?

- A man’s relationship with his mother can tell you a lot about his relationships with women. If he has a close relationship with his mother, it can indicate that he can have close relationships with other women. If he grew up respecting his mother, it can be easily translated into being respectful to women.

One of the main things I recommend for women to do when first dating someone is to learn about the guy’s relationship with his mother. At the very least, it can give you some idea of how he interacts with women.

Be sure to time these questions appropriately. Don’t sit down and ask these three questions and end the date. Also, be prepared to answer these questions for yourself. Being open and authentic yourself can create the space for your date to do the same.

Amanda Patterson, LMHC, CAP - www.amandapattersonlmhc.com

# 9. Discernment is key

Dating is very different than it was twenty or thirty years ago. Women are stronger and more assertive, and they seem to have a better idea of what they want and need as a result.

Because we now live in the fast lane, it only makes sense to expedite the “get-to-know-you” process as well, especially when looking for a life partner rather than simply dating for the sake of dating.

In modern day, both parties generally appreciate the reality of not wasting each other’s time if there is no potential for a viable future together.

As a holistic health psychologist, I always encourage people to look for mates who will align with their deepest soul needs.

This means getting to know yourself before really getting to know someone else so that you can find a good match without sorting through your own confusion. However, there are several questions you can ask your potential soul mate to help you find that special fish in the sea without getting lost in the big ocean.

1. Ask about their top 3 priorities in life—and ask them to be honest.

Their answer provides VOLUMES of information! If their priorities aren’t aligned with yours, then politely excuse yourself and move on to the next fish.

2. Ask what they love most about their life.

Their response will help you dive a little more deeply into a) what they are passionate about, and b) whether they are capable of loving something deeply. If you don’t get a clear answer, then their river doesn’t run very deep and you will likely be emotionally unsatisfied by the relationship. Just keep swimming.

3. If they were deserted on an island and could pick one person from history to be there with, who would that be?

This question could provide LOADS of information for who the potential mate is, what they stand for, and what drives their life. If they want to spend time with that person, then they are likely a lot like them or aspire to be like them. Either way, you get the inside scoop for how they would want to spend their time and what makes them tick.

Discernment is the key to choosing any mate.

First and foremost, you must know yourself as much as possible in order to create a conscious relationship. But in knowing what to ask a potential mate, you can not only save yourself a lot of time in the dating process, you can also align yourself much better with the needs of your soul.

Katherine T. Kelly, Ph.D., M.S.P.H. - www.drkatherinetkelly.com

# 10. Ask these 3 casual questions

No matter how many you’ve been on, a first date can be nerve-wracking. One way to lessen your anxiety is to have a few questions ready to keep the conversation flowing, but not just any questions. Asking on the first date if someone is looking to get married or wants kids often comes across as too intense.

Here are three questions that I think are great because they seem casual, but you can still gather great information about the other person without the pressure of the “big ones”.

What is your ideal vacation?

One goal of a first date is to see if you might want to go on a second one. This question can potentially help you gather quite a bit of information to that end. If you love the outdoors and camping and they say they only stay at 5 star resorts with room service, you might not have quite the same ideas about what “fun getaway” means.

A follow up question could be: Have they ever had a bad vacation?

Listen to how they tell the story and you may learn how they handle stress, surprises, and adapt to change. Did they make the most out of the situation or did they let it ruin their trip?

How long have you lived here?

While at first glance this seems like a dead-end question, it can actually open up a longer conversation no matter how they respond. If they are newer to the area, you can ask about what other towns they’ve lived in, how they ended up in this city, and how long they plan to stay. If they are from the area and you are as well, you can chat about how it’s changed, favorite places, and if you know any of the same people. If you are the one from somewhere else, you can share your journey and get some tips from a local.

Do you have any pets?

This is a great way to connect with a fellow animal lover. Swapping pet adventures is a neutral way to pass the time, but even if they answer, “No, I don’t have a pet”, you can ask why not? Allergies? Work too much? Hates cats? Again, all great info to gather when deciding if you’d like to see the person you are sitting across from again. Maybe you are the one who doesn’t care to have a four-legged friend. If they are gaga over Fido, it could be a new experience for you or a deal-breaker.

Megan Bearce, LMFT - www.meganbearce.com

# 11. Ask the below 3 questions

1. “Tell me about yourself.”

This phrase offered up in a friendly tone, is more than just a question. It becomes an open invitation for him to focus on the topic he knows the most about, and with which he feels most comfortable. Himself. Approaching him with this open ended request lets him know you are interested to learn about who he is as a person. It also gives him the freedom to share with you, at the level he feels comfortable divulging.

Likewise, it permits him to start his answer wherever he wants. He could begin by talking about his work, his travels, where he grew up, his family, sports, or touch on a smattering of all of it.

In turn, this question gives you important clues about what he values and considers important in his life. In general we tend to start with the high points of our lives or significant emotional events. So how he answers this question also helps you see where you have common areas of interest or experiences. That then paves the way for deeper exploration in the future.

Similarly, I would recommend if he starts by giving you a long stream of ‘woe is me’ stories about the series of unfortunate events that characterizes his life, RUN. This usually means he feeds on drama and that in turn is the focus in his life. You'd be best to look for someone who seeks out and emphasizes the positive in life.

2. “If you could do anything, go anywhere, or be anyone, what would that look like?”

Our first interactions with new people are about discovering commonalities, finding potential compatibility, and establishing a framework on which to build a sustainable relationship. The thoughts we allow ourselves to entertain related to the future and our own efficacy.

Asking him this question, may reveal important insights on imagination, hopes, dreams, and goals, and whether he has thought about this, and if he is currently pursuing them or not.

It also gives you an indication of how healthy he is mentally. People who have severe psychological issues tend to be restricted in their ability to imagine or dream when discussing what their future could look like.

However, if you realize your own ability to dream was stifled, now is an ideal time to seek healing from the things in life that may have knocked you down.

Be prepared to share your hopes and dreams of adventure as well.

3. "What would you like to know about me?"

Now, this may seem like a strange question to ask a guy on a first date, especially since as women, we have largely been raised to focus on the man. However, in a healthy relationship, it is just as important for him to be interested in you, as it is for you to be interested in him. It may seem a little risky to ask this question, but wouldn’t it be a lot better for you to know where his interests in you lie from the beginning?

This may weed out some of the guys who say they are interested in you as a person but are more concerned with a mere sexual relationship.

When you chose to answer this question, offering a healthy mixture of high points and a couple of major struggles you’ve gone through helps keep it real, because life is never ALL good. It’s a mixture of good and bad; and talking about how you succeeded through the difficulties helps him see your ability to overcome and be resilient. Along the same lines, it would be helpful to know how he has overcome some challenges, too.

So, think about what you want to share on the first date, and how you want to go about sharing it.

What is important for him to know about who you are, what are your interests and hobbies, and what are some of your hopes and dreams?

For instance, “I want to get married and have kids” may be what you desire, but if you share it that way on a first date, it could scare the guy away. However, encapsulating that truth in your hopes and dreams for the future framed like this: “Someday I hope to get married and have a family of my own,” gives him a glimpse of your future dreams, yet frees him to possibly picture himself in your future, rather than feeling as if you have already placed him there.

In conclusion, I believe the more freely the conversation flows in both directions, the greater the indication that you both have enough important common interests to form the foundation of a healthy growing relationship, and the possibility of a compatible future.

Charlene Benson, LPC, NCC - www.bensontherapist.com

# 12. Ask the below 3 questions

First dates can be tricky…. Let’s face it… there are so many layers to compatibility and you never really know how you will connect with someone or if you will at all. That said, there are a few go to questions that can help to break the ice and allow you to get to know your date better without making things awkward.

1. Where are you from?

In fictional writing it is said that to truly know a character you must first understand “where they are from” not just physically but also emotionally and spiritually. …. When they answer with the location listen and learn, maybe ask some deeper questions such as; what was it like growing up there? What is your favorite thing about your home town? ….and also let them know you are also asking them emotionally and spiritually where they are from… what are key things that make them who they are?

Emotionally available mature men will not only be happy to answer, they will be inspired by the depth of your questions.

2. What are you passionate about?

Instead of simply asking them “what do you do?” as in how do you pay your bills and make a living, ask them what makes their tick tock…. Hopefully their passions will be alignment with their career as well, but let them know that you are interested in how their heart works and what makes their soul soar. This will also reveal to you if you have some similar interests and passions in common, this in itself can branch off into a full conversation with the right person.

3. What are some of your future goals or adventures?

It’s always smart to check in with your date and see where there mind and heart is in regards to the future… are their future dreams to travel the world? To settle down get married and have children? To write a book…. etc. etc. this will also reveal to you whether or not you might be compatible long term and if you are dreaming about the same or very different things.

Now, remember to stay open minded as sometimes our desires wants and needs can change through time and relationship but the reality is if your date never wants to leave their home town, wants to attend church every Sunday etc. and you are looking to travel the world and create your own spiritual “church”… chances are, it’s not going to work long term and it is better to be aware of that before you become to invested.

When asking your date questions remember to keep it organic, allow conversation to flow naturally and be yourself, you don’t want your date to feel like it’s an inquisition or an interview.

Yes, you are attempting to learn more but you are also more importantly seeing if your energy is compatible and that’s much deeper than the right answers or how someone looks on paper. It’s a dance…. A back and forth that should feel effortless with the right person.

Ashley Davene, Relationship Counselor - www.ashleydavene.com

# 13. Consider asking questions to yourself first

I would say first dates are more questions to yourself about how you feel before, perhaps during, and then after the date as you reflect on the experience.

Ask your questions of your Wise Mind, meaning the intuitive center of yourself on how or what you observed, how you felt physically around him and what stood out to you about him.

Intuitively, listen to yourself versus giving yourself the answer.

As you do this, perhaps reflect on the questions you would want to know about him or his answers, whatever they are.

The first date I would suggest being in the moment versus trying to get answers, this is more intimate, more authentic and less pressured.

Lisa Bahar, MA, LMFT - www.lcbahar.wix.com

# 14. Know more about his typical day, goals and his family

1. What does your typical day/week look like?

I like this question because it can tell you a lot about a person and what to expect from them if your relationship progresses. It'll also give you a sense of whether their lifestyle fits with yours as well as how you may need to shift your lifestyle to accommodate theirs- which is important in a developing relationship.

Are they a workaholic to the point where you'll never see them?

Do they like to party every weekend with friends whereas you prefer to stay in?

Are they well-rounded, allocating time for work, friends and family?

2. What are some goals you are working towards right now?

This question is great because it gives you a sense of what their priorities are at this time.

Are they looking to save to buy a house? Get a promotion? Travel more?

Do they even have a sense of direction in life? Do they have goals at all?

You may also get a sense of their maturity level and values through this question.

3. Any sort of questions related to family. Where did you grow up? How many siblings do you have? Are you close to your family? What are they like?

The way a person relates to their family can say a lot about who they are, their values in life and their readiness for a relationship. Our familial relationships and upbringings also impact our relationship framework as well as our parenting frameworks. We all carry "baggage" related to our families and upbringings, and so talking about this may give you a sense of what each of you is bringing into the relationship.

Kasey Opperman, MSc, RP, RMFT - www.kltherapy.com

# 15. Explore where he lives, his values and hobbies

Depending on the person, first dates can be fun and exciting, and they can cause some level of anxiety. Women who are introverted may struggle more than their extroverted counterparts because getting to know someone new requires an output of energy that can be exhausting and overwhelming.

Women who identify as extroverted may find it easier to meet and learn about a new person by engaging in animated dialogue because that’s one way extroverts fill up! Introverted women can often feel pressure to fill in silences with small talk, which can feel exhausting and boring. I thought it might be helpful to focus on a few tips that might help introverted ladies feel less stressed about meeting someone new and entering into meaningful first date dialogue.

If you're introverted it's possible to feel reticent to go on the date, especially if your energy stores are already feeling low…say it’s on a Friday after a tough week.

If that's the case, prep first!

Try doing something soothing to regain your center and energy back. What helps you to feel energized for other-focused connection? A nap, reading a favorite book, a bath, journal writing? If you need alone time to boost your energy beforehand, do it! You'll feel more ready to engage in first date fun if you've addressed your restorative needs first. (It’s also great training for your date down the line if there is a match. They’ll notice if you’re feeling depleted and hopefully, can recognize (because you’ve told them and they have some level of perception), that you need to recharge. Let’s move on to the date!

Listen to your gut and pay attention to your energy.

How does it feel to sit with this person? What does your gut say about the potential for a second date? Are you feeling like running away when the salad shows up? Is there something about this person that feels comforting? These are all great questions to ask yourself.

Here are some questions you might want to consider asking your date and why they could be important.

1. Do you live alone or with other people?

This is important to know, especially if it turns out that your date lives with several other people. I’m not saying this is a deal-breaker, but if you feel a connection, and think you may want to spend time there, it’s probably worth talking about and getting more information about his living situation and social connections within that circle.

2. What do you value in relationships?

If this feels like too loaded a question, you can ask about friendships instead. It seems the benefits to knowing these answers would be helpful for anyone, but knowing this early on could strike a chord in you that makes connecting easier. You get to listen and learn by asking a great question instead of fighting to make small talk grounded in nervous energy. Based on his response you might learn something about yourself as well, and that is a great thing!

3. What is your favorite hobby or hobbies?

If he’s at every single college football game at his alma mater during the season and that’s not your thing, that could be helpful especially if he doesn’t expect you to go. You get alone time! Yay! Or you might discover that the wine and painting class you’ve repeatedly snubbed might actually be a fun way to explore your creativity (and taste in wine) in a way that keeps the spotlight off you.

Overall, I think the key for successful first dates is to keep your expectations low. Don’t sabotage yourself by wondering if it will be a disaster. Learn from him, listen and just be yourself. If compatibility is there you’ll know. If it’s not, you’ll know that, too. It’s one date, it’s not the rest of your life. Enjoy your meal or activity, think about how the experience can enrich your life in some way, don’t stress if he doesn’t seem into you. You’re already a great partner for someone, perhaps you just haven’t met them yet. If the date falls flat, you can try again with someone else when you’re ready. In the meantime, there is always wine and Netflix. Cheers and good luck

Sandra Labo, MA, LPC - www.sandilabo.com

# 16. Ask questions that are organic and possess a certain ease

First dates can be interesting. Spending time with someone you don’t know very well, assessing if you are compatible with this person. First dates should be fun, a tad nerve wracking and altogether exciting. It can feel like a lot of pressure, so try and take it easy by keeping it light and remember there are no strings attached.

Try not to overthink too much during the date but take note of things that stand out to you both positive and negative, including the quirks. You’re looking to see if there’s some kind of connection which should feel somewhat organic and possess a certain ease.

Here are some questions to ask that can help stimulate the conversation and keep it going.

- “What’s your ideal vacation?” ­– this allows you get to know whether your date is more on the adventurous side, laid back, or a little bit of both. This also opens up a conversation about places you’ve been or want to go to.

- “What are some of your favorite places to go around here?” – this light and easy question can open a further discussion of possible common interests as well as a potential opportunity to plan a second date and go to one of the places you discussed.

- “Whose been the most influential person in your life?” – this can lead into a deeper discussion and allow your date to open up about a person in their life or someone they look up to and which qualities that influential person possesses that your date is inspired by.

Shannon Behar, MFT – www.shannonbehar.com

# 17. Don't be afraid to think outside the box and consider asking the below questions

It’s no secret—while dating can be fun and exciting, it can just as easily be saddening and frustrating. Plenty of us would rather sit through a job interview than a first date with a stranger, despite the similarities of the two conversations. Just as you would prepare for your job interview to ensure it goes well… or at least as well as possible… so should you prepare for a first date. That’s why good first date questions are so important.

Communication Skills 101 teaches us that the easiest way to keep a conversation flowing is to ask your date questions to learn more about him, what he likes, what makes him tick, etc. The key to successfully vetting a prospective relationship partner on a first date, while at the same time keeping the mood light and fun, is knowing what questions to ask and how to ask them.

As an example, asking about favorite interests and activities, recent books read and concerts attended are nice ways to get to know your date. Topics I would urge you to avoid, especially early on, include religion, politics, and exes. Don’t get too heavy, too quickly!

Stand out from the crowd by asking more interesting questions by avoiding the standard “So what do you do?” and inject some fun and energy into your chit-chat while you get to know your date. If you ask the right questions, all the while listening for interesting nuggets on which you can probe further, you’ll be surprised how much you’ll be able to learn about a person.

Consider popping these questions on your next first date and see where they take the conversation. If nothing else, you’re bound to learn some interesting tidbits about your companion.

1. What do you like and hate most about the dating process? (I use this question as an interesting way of avoiding unknown pet peeves and potential landmines as I get to know my newly-found friend.)

2. What’s the most thoughtful gift you’ve ever given/received? (I want to see how thoughtful and considerate someone is of others and their preferences. Will he put some effort into picking out the perfect gift for me and will he appreciate the effort I put in to doing special things for him?)

3. What are the top 3 things on your bucket list? (This question gives me insight into what my date is interested in and perhaps has a passion for. And if things go well, it could be a fabulous surprise gift idea down the road!)

AND A BONUS QUESTION: What should I know about you that I’d never think to ask? (I LOVE this question and have received all sorts of attention-grabbing responses—some funny, some a little embarrassing, some quite telling, but all interesting!)

Don’t be afraid to think out of the box. With all the cookie-cutter first dates we’ve all been on, set yourself apart from the rest and demonstrate your creativity, fun, and uniqueness. I guaranty it will yield more second dates!

Deb Daufeldt, MA, MBA, NCC - www.newchaptersolutions.com

# 18. Explore his willingness to take accountability and learn about his coping mechanisms

1. Why did the last relationship end?

This question gives you lots of invaluable information. Does he blame everything on the ex? Find out why. Get the details because how he tells the story will say a lot about how he functions in intimate relationships.

For instance, if he tells a good guy/terrible gal version, it indicates a lack of personal accountability. That is a major red flag.

Another sign is portraying himself as a victim. If everyone is wrong but him, expect that to show up in your relationship eventually.

On the other hand, if he talks about his own mistakes and has some insight into his own behavior, that’s a good sign! You are looking for his perspective on relationships.

2. How does he handle emotions?

This is critical because if he doesn't handle or acknowledge emotions, coping with life's challenges is going to be difficult. When the chips are down he won't be able to cope well. He may develop destructive coping methods like drinking or other compulsions. If he becomes an addict, it will set you up for a lifetime of heartache.

Watch carefully because this one takes time to see. Wait until after the honeymoon stage where everything stops being perfect. You'll be so glad you did!

3. When there is a problem what does he do?

Does he handle a problem directly or does he avoid it? Does he drink to avoiding dealing with it? Life comes with problems so if he doesn't have the skills to handle life on life's terms, you're in for a long haul.

Or, does he spend a lot of time fixing everyone else’s problems? This can be a sign of codependency when you are giving too much for approval. If he loves being the hero but neglects his own obligations that’s not going to work long term. You won’t feel like you have an equal partner.

Michelle Farris, LMFT – www.counselingrecovery.com

# 19. Ask questions that mean something to you

For me to suggest questions for a woman to ask on a first date, I would need to know the woman.

Each woman, as an individual, has different needs, and therefore what would be important to one might not necessarily be just as important to the next one. I would most definitely ask her to consider what is important to her in her life and for her relationship.

When meeting a guy, if you’re interested in seeing him again, ask questions that mean something to you.

In this case, you must know yourself. It’s very difficult to get to know someone else when you aren’t clear on who you are. Once you’re clear on who you are, you know your requirements, needs, wants, likes, and dislikes, then ask away of what interests you about the other person.

More than being concerned about the “right” questions to ask a guy on a first date, try connecting, relating, and getting to know the person, while having a good time with him.

This way, if after that you decide to see him again and the feeling is mutual, then take it from there and let your inner guidance kick in and direct you, based on your knowledge of yourself, and trusting you. Hope this helps.

Barbara Ann Williams, LPC, MS – www.barbaraannwilliams.com

# 20. Try these 3 engaging questions

If you are like me, then you probably don’t like to waste your time. Let’s face it. Time is precious, and we want to spend it on people and activities that bring joy and value to our lives.

Dating can be pretty time consuming, and it’s important to get to know your date on a deeper level before making any serious commitment.

How do you know if you are compatible? How do you know if he is trustworthy? What does he value in life? What kind of food does he eat? What are his hobbies?

I believe asking fun and engaging questions can be a great way to learn about your date pretty quickly.

The answers to your questions can tell you a lot about a person, and how they think and respond to life. Questions also keep the conversation going when there are awkward silences or long intermissions between conversations.

3 Engaging Questions to Ask on the First Date:

1. If you could be anyone in the world for a day, who would it be and why?

This question can tell you a lot about who your date admires and what he values in life. Does his answer reveal that he admires someone who makes a lot of money? Loves animals? Respects women? Listen attentively to his answer, and notice the clues it tells about him.

2. What is your fondest memory from childhood of your father? Or your mother?

The answer to this question will tell you a lot about his experiences growing up. Our relationship with parents often set the tone for all future relationships. What does he say about his mother? Is it all positive or all negative? Does he put his mother on a pedestal?

3. What is the longest period of time you’ve gone between relationships?

I like this question because it reveals a lot about his emotional and physical needs. Does he need a lot of time to process one relationship before starting another one? Does he jump into relationships quickly? Allow him to answer the question slowly and thoughtfully. Give him time to consider his answer.

While I believe asking great questions can tell you a lot about the heart and soul of your date quickly, I also believe that your first date should be light and fun. Take your time asking these questions. This is not an interview. Don’t’ go in there with a clip-board, a stop watch, and a serious look on your face. Be curious and open about your date. How does it feel to be with him?

If you enjoyed yourself, let him know. If you didn’t, thank him for the date, and let him know that it wasn’t a match. This allows you to leave the date with clarity, and a positive impression of you.

Dr. Shannon Tran – www.shannontranphd.com

# 21. Ask questions that matter to you and your values

When we have a first date it brings with it the same level of importance as a job interview or interview to get into a collegiate program, but we often do not even plan or think about the questions we might want to ask and the things we want to know so we can decide if we would like to meet again, spend time, invest emotionally etc.

We should plan for our first date with the same importance we give other areas in our life. Beyond our outfit and hair, we need to think about what is really important on a first date.

First question to ask on our first date is: What are your deal breakers and must haves in someone you date?

If we have complete opposite deal breakers and must haves, why would we devote more time and investment to have issues we cannot overcome. Instead ask and decide if there is even a level of compatibility in these two areas before we meet again or call it a nice to meet you and I hope you have a great life date.

Second question to ask is: What is the children situation?

We want to know if they have children in case this could be a situation we might have an issue with or have feelings about. Do they have an issue dating someone that has children if we do. Also, do they plan on kids in their future, this could be or not be an issue for us depending on where we sit in our lives. Also as a side note if this throws someone into freak out mode then do we really want a second date, I think that bears serious consideration.

Third question to ask is: Are you close to your family?

This can let us know how they feel about their family. It can also show red flags if they are in an enmeshed relationship with their mother, no relationship with anyone in his family and why. It could really tell us a lot about the person and see if we have compatibility in this area of our lives.

These are my top three questions, but whatever the questions you ask on a first date they should matter to you and your values. They should help you feel more comfortable in accepting a second date or parting ways. Ultimately, we should devote as much seriousness and thought to our relationships in life that we do to other areas.

Neesha Lenzini, MS - www.relationshipsinneed.com

# 22. Consider the ideas below to break the ice and open the dialogue

So he asked you out….now what?

First dates can be filled with anxiety, anticipation and dread. Before panic overwhelms you recognize every situation is different, there is no right or wrong. Think of this as an adventure and embrace the experience. This is your opportunity to test the water and find out if this person is someone you would like to get to know better. It is the perfect time to set the tone for future conversations, open-ended questions are key to getting communication flowing.

Here are some ideas to break the ice and open dialogue.

1. What excites him…what is he passionate about?

This clues you in on where his head and possibly heart is at. Is he passionate about career, education, friends or family? This may reveal some of his values and help you to better understand where his focus is.

2. What challenges him?

This gives you insights into how he interprets obstacles and navigates challenges. You may get more information on the level of stressors in his life and how he manages them. Is he easily overwhelmed, dependent or able to take charge of situations?

3. How does he like to relax and recharge?

This question sounds benign but is very telling. For instance, some may choose to watch a movie, take their stress to the gym for a workout, go with their friends to the bar for a drink or engage in high risk behaviors. Does he rely on healthy positive sources of relaxation or engage in behaviors that may not be in line with your habits or preferences.

Pay attention to the way you feel as you interact and receive information. What you have learned? Is this someone you would like to get to know better? Does it feel like friendship or possible romance? Only time will tell. Remember to relax, have fun and be open to the experience.

Stacey Shumway Johnson, LPCC-S, LICDC-CS, BCC - www.2xlcoach.com

# 23. Be open minded and ask open-ended questions

Relationships are based on connecting and relating to one another. In today’s world, people are often privy to information about the person they are dating. With social media, dating sites, and google, we are inundated with information at our finger tips.

Although when it comes to connecting with another human being, especially romantically, consider ways to authentically get to know the person you’re on a date with.

Use open-ended questions as a way to relate to your date.

Try to avoid questions that stop the conversation short, like anything that would end in one word responses.

Open-ended and exploratory questions let your date know you are interested and have a desire to get to know him.

“Tell me about yourself” is a good place to begin any conversation.

1. What are you most proud of in your life?

This question highlights someone’s values and provides a compass into someone’s inner world. Look out for superficial versus authentic responses. An example of a superficial answer would be listing material possessions. On the other hand, an authentic response would be one’s family, caring for others, one’s education, serving others, engaging in any volunteer or charity work, and sharing how your date has helped others in life.

2. What’s an example of a challenge you overcame?

This question illustrates how resilient your date is and how brave this person is when faced with adversity. It also reveals vulnerability and how comfortable your date is with not always being in control. Men often times struggle with this concept, so if he can share something he’s struggled with, he is able to emotionally open up with you.

3. Where is your favorite place to spend time?

This question shows us who your date really is. When this person has down time, where does your date like to go? Look again for superficial versus authentic responses. An example of a superficial response would be: “bars, the gym, shopping etc.” There is nothing wrong with visiting any of the above aforementioned places, but if this is your date’s favorite place to spend time, it illustrates a superficial lifestyle.

On the other hand, if your date shares places like: “church, spending time with family, visiting a favorite vacation spot, or participating in a hobby he enjoys” then you can identify that he is showing you his authentic self.

More than anything, try to be flexible and adaptable within your conversation. Practice active listening which means you are deeply hearing and validating the other person.

Bring your authentic self to your date and practice answering openly as well if you are feeling a connection.

Brooke Campbell, MA, LCAT - www.creativekinections.com

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