December 2, 2017

7+ Fascinating Insights On How To Know If a Guy is Worth Pursuing

How To Know If a Guy is Worth Pursuing

“Being deeply loved by someone gives you strength, while loving someone deeply gives you courage.”

~ Lao Tzu

# Consider the below questions
Caitlin O Gallagher

So you’ve swiped right on a handsome guy and it’s a match.

You’ve been texting back and forth for a few days - some days it’s going well and the witty banter is off the charts and other days he goes silent for a while and you’re not sure how to read him. You probably find yourself asking the question, “Is this guy worth the work? Should I keep pursuing?”

The truth here is that there is not one answer, but instead the answer is going to be different depending on who is asking the question.

You bring your own history, communication style, beliefs and behaviors to a relationship, just as he does. It always takes two to tango. 

Here are some useful questions to ask yourself as you work towards determining if he is worth pursuing:

What are you looking for?

Are you in search of something fun or a serious commitment? Someone to do adventurous things with on the weekends or someone to open up to about your struggles and intimate secrets? The answer to this question will likely change if you think a guy is worth going after. If he doesn’t seem like he wants a serious relationship right now and you don’t either, then maybe it’s just what you need. 

Do your interests and values align?

Are you a vegetarian and he loves to travel the country visiting the best BBQ joints in each state? Do you know you want children and he has his sights set on a childless future? Do you love hiking and camping on weekends while he prefers going out drinking and watching reality tv shows in bed all day on Saturday?

Basically, what do you both have in common? What are your differences? Do you have enough in common and do your values align enough that you could imagine living a life with this person without sacrificing too much of your own beliefs? This brings me to the next question. 

What are your compromises versus deal breakers?

What are the things that you are willing to work with versus your deal breakers? You won’t align in every way, and compromise is a necessary skill in relationships. What’s key to compromise is knowing the line between being flexible and sacrificing so much that you lose your own values and goals in the process.

Are you being respected and treated the way that you want?  

This is the last and important question to ask no matter what you are looking for in a man. At the end of the day, you deserve to be treated with respect, gain what you need from a relationship, and feel generally positive about your interactions, even when they aren’t always pleasant. If a friend was in your shoes what would you tell them? 

Exploring your answers to these 4 questions will help you gain some clarity as you figure out if he’s really worth pursuing.

Caitlin O'Gallagher, LICSW –

# Values + Vision + Attraction + Inner Knowing

You’ve been dating for this person some weeks and there’s a lot to like to be sure.  For example, you enjoy each other’s company and the physical attraction, at least on your part, is undeniable. But you wonder if there could be something more – could this relationship lead to something more enduring?

Well, firstly, it’s early days, isn’t it?

While you may know some things about your lover, there’s a lot more you don’t know. Sure, a bit of mystery is intriguing, but when it comes to commitment, the mystery factor is not the best predictor of long-term viability.

So, what it comes down to is getting to know this person more deeply.

That requires taking some risks – taking the risk of revealing more about yourself, the deeper stuff that you normally keep hidden, because you don’t want to scare a lover off.

Those things might include your hopes and dreams for your life and what you desire in a relationship going forward. And it’s taking the risk of asking your lover what is important to them in life and relationship. You may feel some trepidation taking the relationship deeper, but these are necessary areas to explore in order to gauge how well you’ll travel together as a couple in the longer term.  

Basically, what you are looking for is how well-matched are.

You want to know if there is enough substance in this relationship for the long haul, especially when the going gets rough, as it inevitability will.

There are probably a lot of indicators of compatibility, but let’s look at some of the big ones.


What do you value the most in yourself and in another person? By that I mean those things that you care most deeply about. These could include qualities like: trustworthiness, respect, community, creativity, compassion and spirituality. Symmetry between your values and those of your lover is essential for long-term commitment. So, take some time to consider what your most important values are, then write them down so that you are very clear about them.

Values Question: What are your values and how similar are your values to those of your lover?


What vision do you have for your life? What do you want your life to look like in 5 to 10 years from now? What kind of life do you want to create with a partner? Write this down too so that you are clear about it.  As well, symmetry between your vision for the future and that of your lover is vital for long-term commitment.

Vision Question: What is your vision for your life and does your lover share a similar vision?

Physical Attraction. 

Physical attraction is important and not to be discounted, because it will be the glue in your relationship.  It’s biological and can’t be manufactured. Sometimes it’s instantaneous and sometimes the attraction grows as you get to know someone more deeply and begin to appreciate their qualities. But it needs to be mutual.

Attraction Question: Do I feel a physical attraction to my lover and is it fully reciprocated?

Inner Knowing.

What does that quiet inner voice (or your gut) tell you about this lover of yours?  I refer to all those things that are beyond the workings of the mind? Your inner knowing or intuition is informed by the sum of everything about this person:  their behavior, their words and everything in between. For example, remember a time when you could just sense that something was off regarding a situation or a person.  Then, remember a time when you just knew that a relationship or situation felt very right. You just felt it in your bones. Too often we try to talk ourselves out of this deep knowing to our own detriment, because we allow our mind to talk us out of it.

Inner Knowing Question: What does my inner knowing tell me about my lover? Do I sense that this a safe, respectful and wholesome relationship?

In conclusion, if you want to know if this relationship is worth pursuing, you’ll need to open the door to a deeper kind of intimacy between you – let’s call it emotional intimacy – that which includes and is, at the same time, beyond the physical.  But you don’t need to rush it.  Pace it out. Allow it to flow naturally. Just begin with your own sharing, gentle asking and attentive listening.

And don’t ignore your inner voice.

Mary Rizk, Transformative Coach -

# The pursuit should be mutual

Two things: one: only you know if a guy is worth pursuing and two: how do you define “pursuing”? 

Is pursuing showing interest and occasionally initiating a date?  Or is pursuing obsessively following him on Facebook, following him in your car, staking him out at locations where you know he’ll be?  In other words, stalking.  If it’s the latter, stop. No guy is worth losing your dignity over, or possibly going to jail!

Isn’t dating how we find out if a guy is worth pursuing?

How can you possibly know if someone is worth the time, energy and inherent vulnerability of pursing if you don’t know him.  If someone seems to meet your basic requirements for a partner, I say by all means pursue.  

Although it still seems that most of the time men are expected to take the lead, the occasional, “Hey I have tickets to a Padres game.  Would you like to come with me?” is fine.  Or just invite him for coffee. You’ll know by his response if he’s interested in you, and hopefully during the game or coffee you can find out more about him.

If he’s not interested or really lukewarm (i.e. isn’t into getting to know you, but can’t pass up tickets to the game), forget him

All the pursuing in the world isn’t going to make someone be interested in you if he’s not.  This is not a judgment on you; it’s about him.  There are many factors that go into wanting to pursue a relationship.  You are only in the know about your factors; you don’t know anything about his.

In a reasonably short period of time, the pursuit should be mutual.

This is another way of saying that it takes two interested parties to create a relationship. You don’t want to be doing all of the work. Taking a risk to make the first move is really OK. But you are entitled to expect some reciprocity. If you aren’t getting it, I say pursue someone who wants to pursue you.

Sally LeBoy, MFT –

# Take your time + establish boundaries + maintain open communication
Lisa Angelini

First, let us address the topic of “worth”.

Every person has value and worth just because they are living and breathing.  Whether you want to be in a relationship with someone, is something altogether different.

Determine your goals for dating.

Ultimately, are you looking for a long term committed relationship or a casual dating experience?  If you are looking for a long -term relationship, you will need to pay attention and not settle for less than what you want.  It is important to get clear on what you want. What experience do you want to have in your relationship?

To do this, identify what qualities you would like your relationship to have.

For example, would you like your relationship have the following qualities: light- heartedness, committed, fun, heart-centered, supportive, mutually respectful, loving, sexually compatible?

You must elaborate in detail and have a very clear picture to attract the experience that you want. In my work as a dating and relationship coach, a common client theme is that they desire a relationship so much, they end up ignoring obvious signs and signals that a relationship may not be worth pursuing.

What partner qualities are important to you?

For example: funny, creative, sexual, spontaneous, grounded, loyal, good communicator, financially responsible, likes to travel, sense of spirituality or not? Again, be clear and detailed here.

What personal qualities do you bring to the relationship?

Some women have trouble with this one especially if there are issues with self -esteem. You must be that which you want to attract. If there is unfinished healing work of your own to do, now is the time to engage.  Perhaps your own qualities are that you are caring, loving, fun, loyal, committed, good listener, family-oriented, etc. Remember, you are a prize. For someone to value you as such, you must realize this yourself.

Most importantly, what are the deal breakers? People will have different ideas of what might be a deal breaker for them in a relationship. Some common ones are: Smoking, drinking, drug use, certain political affiliation, disrespect.

Make lists of these qualities. If someone does not meet the criteria, but you are wildly attracted to them, don’t pursue it. Physical attraction alone will not be enough to sustain a fulfilling relationship.

Now, that you have gotten clear you can focus on him and if you want to pursue him further.

Ask questions and listen to his answers. Are his answers thoughtful or dismissive? Does he seem to be straightforward in his approach or elusive and avoidant?  We are looking for transparency and openness.

Does he seem generally interested in you? Does he ask you questions and really listen to the answers? Does he ask further questions after he gets the answers?

Do not make excuses for behavior that is not considerate of your time or feelings.

Is he happy to see you? Does he reach out to you – calling and texting often?

Does he ask when he can see you again?

Are his actions clear so that you don’t wonder if he likes you?

Are his words and actions consistent?

Does he do what he says he will do?

Take your time.  We are all on our best behavior at the beginning of a relationship. Only time will reveal certain habits, tendencies and behaviors. If you have concerns in the beginning this should be alarming to you. Remember, this is his best behavior.  Run fast in the other direction.

Most importantly, honor your intuition. If something doesn’t feel right, it probably isn’t.

Lisa Angelini, MAPC, LPC -

# Ask yourself how you feel when you are with him
Nancy Harris

I’m sure there isn’t a woman out there who hasn’t wasted precious time on a guy who simply wasn’t worth it. It can be easy to see in retrospect all the red flags that you ignored and wonder why you didn’t take them seriously at the time. You live and learn. And, hopefully, get wiser with each experience.

So how do you know if he is worth pursuing?

You want to notice first and format how you feel when you are with him. 

Do you feel relaxed, seen, heard and cherished?

Does he treat you with respect? Are your feelings and wishes honored? Is he trying to get to know you in a sincere and deep way or is it all about him? Does he do what he says he will do, call when he says he will call and show up as he promises? Is he honorable and trustworthy?

It is important to remember that actions speak louder than words when getting to know a new person. It is easy to promise the moon and stars, and talk about a rosy future, but does he walk his talk? 

Words are meaningless if they are not acted upon.

You also want to look at the state of this man’s life. Is he close with friends and family? Is he able to maintain stable relationships and hold down a respectable job? Does he have dreams and goals for his future or is he lost and adrift?

As a relationship coach, I see on a daily basis the common problems that ruin relationships and cause untold pain.

Don’t expect a person to change if you see non-negotiable traits such as addiction, chronic anger issues or unfaithfulness.  If he is irresponsible and immature with money, be aware that this could also be a life-long trait. If someone is unwilling to learn healthy communications skills, there will most likely be future problems.

So many women enter and stay in relationships thinking that the man will change his bad habits if she just loves him enough, is patient enough, or helps him change. This is a project you may later regret taking on. You cannot change another person. He has to want to grow, heal and change himself. 

One question I would ask a man early on in a relationship is if he would be willing to go to therapy in the future if the relationship becomes serious and issues needed to be worked out. If you are with a man who says he would never go to therapy, you are dealing with a difficult situation should you hit an impasse.

Refusing to seek professional help says something about a person’s willingness to work on the relationship and the value that the relationship holds for them. This is a serious consideration that could undermine future happiness with this person.

Far too many relationships that I see are simply too much pain and work.

It really shouldn’t be that hard. Yes, relationships take work, but how much work is the question. It is important to choose wisely and know when to walk away before too much time is invested. 

Go slowly in getting to know someone and pay attention to the red flags. Notice if the man you are pursuing is open to feedback and personal growth or stubborn, defensive and set in his ways. Healthy relationships are created by two healthy people who are taking responsibility for their own lives. 

As Maya Angelou once said, “When someone shows you who they are, believe them the first time.”

Nancy Harris, LCSW, LICSW -

# Watch out for the below 6 signs

Women meet many men over a lifetime and it’s crucial to know which ones might be keepers. Of course, we can’t know that right off the bat, but we can ascertain who’s worth pursuing as we get to know them. Points to consider include the following:

#1. How he treats you

Too many women settle for being treated poorly in a romantic relationship. Or they accept a mixture of being treated well sometimes and not so well at other times. Emotionally healthy men will treat you well almost all the time. You may passionately disagree, but you won’t be mistreated. You may decide to slow things down and even take a short break from each other, but he will be kind, compassionate and have your interest at heart as well as his own.

#2. How he treats other people

Seeing how your man treats others can be a real eye-opener. Is he courteous and fair with everyone or does he act superior to people in lower classes or lower status jobs? Does he seem comfortable in his own skin or out to impress, perhaps telling small fibs about himself or going out of his way to seek approval? It’s especially important to see how he engages in disagreements and competitions—does he always need to win or does he know how to handle losing, mistakes and failure?

#3. Whether you share similar values

You will have the best shot at long-term happiness with a man who shares the same values as you do. Values are our deeply-held convictions on topics such as politics, religion and the purpose of life. They are the conscious or unconscious basis of how we choose to live our lives. Although you may be attracted to a man because you both love art films and sushi, that does not make him a worthwhile match for you. You will need many long discussions and time spent together to learn about a man’s values.

#4. Whether you share similar lifestyle views

As with values, it’s important that a man wants to live a similar lifestyle to what you seek. If he’s a nomad and you’ve purposely never lived anywhere but your home town, you’d better think twice about hooking up. If his ideal lifestyle is buying a tiny house and yours is to live on a sprawling farm, he may not be the best match for you. Of course, if you’re looking to change your lifestyle, a man who’s the opposite of you in this regard may be just the one to help you broaden your horizons.

#5. Whether he is emotionally healthy

Perhaps, this, above all else, makes a man worth pursuing. Emotional health is found in introverts and extroverts, men who are brilliant and those who have more common sense than education, rich and poor men alike. Among other things, it’s about his having: reasonably high self-esteem, good boundaries (he knows where he ends and you begin), a stable sense of self, sufficient self-knowledge, curiosity about himself and the world, the ability to identify and express feelings, the capacity to be vulnerable, comfort with dependence and independence, compassion for himself and others, and a view of you as an equal. You also want to look for someone who’s addiction free and that includes, alcohol, drugs, work, gambling, pornography or computer games.   

#6. He is interested in pursuing you

A man is not worthwhile pursuing unless he’s as interested in you as you are in him. If he’s distant emotionally or his comfort level is having an on-again-off-again relationship, don’t bother. If you’re looking for Mr. Settle Down, don’t settle for Mr. Run Around. His value does not increase because he’s hard to get. He’s hard to get because  he’s not looking for a meaningful, long-term relationship.

Obviously, there’s more to what a worthy potential partner might need to have for you to pursue him, including being sexually attractive to you. The above factors embrace only the basics. So, if you find most of them in a man, pursue away.

Karen R. Koenig, LCSW, M.Ed. –

# Watch out for the below 5 signs
Jacklyn B

Here are some tips that can help you figure out if the man you are interested in is worth pursuing.

#1. He is respectful. 

He never calls you names or hurts your feelings. He treats others around him with the same respect he shows you.

#2. He keeps his word. 

If he promises you something, then he always follows through.

#3. He is reliant. 

He follows through not just on his words but also his actions. If he says he will take you to see that movie you've been waiting to see or he tells you he will take you to try that new restaurant that just opened up. You know you can depend on him.

#4. He goes out of his way for you.

He drops you off at an appointment even though it is out of his way which means his commute will take longer than usual. He doesn't mind it because he cares so much about you that he wants you to be comfortable. This shows that he wants to take care of you.

#5. He is kind. 

He is giving and kind to you with his time and attention. He makes you a priority in his life and you truly feel special. He gives you his attention when you are feeling down and cares enough to ask whats wrong. He gives you advice on issues you are dealing with. He brings you flowers or a small gift once in a while to make you feel special. It doesn't have to be an extravagant gift, instead just something that he thinks you would like which shows his thoughtfulness towards you. 

Jacklyn Bystritsky, LCSW –

# Consider the below 5 points

One of the biggest hurdles in the dating game is to find the right match

It is very difficult to be patient when all of your friends are settling down into relationships while you are still waiting to find your “Mr. Right”.  This desire to ‘nest’ can create a lot of pressure and make you more apt to overlook warning signs that you are heading in the wrong direction.  How do you keep your bearings and know if the guy you are attracted to is worth pursuing?  

Here are some points to consider:

1.  How do they manage stress?

Are they able to cope adequately or do they engage in negative, addictive or violent behaviors?  Poor coping skills can contribute to destructive relationships with poor outcomes, do not minimize or excuse away these types of issues as they create major obstacles in relationships.

2.  Are they ‘plugged into’ the relationship?

Is the relationship a priority for them

3.  What is their communication style and how does it mesh with yours?

Are you able to have meaningful conversations and resolve conflicts in a healthy way?

4.  Does the relationship feel balanced?

Lopsided relationships tend to breed resentment so it is important to feel mutual support.

5.  Finally, time for a reality check.  

Does the “potential” of the relationship match the reality?  You have to accept the person you are with as they are today, not who you “think” they are capable of being.  The way things are at this moment, may be the way they are in the future.  If that is the case, is this relationship going to be ‘enough’ for you? 

Stacey Shumway Johnson, LPCC-S, LICDC-CS, BCC -

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