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August 24, 2018

Interview With Amy Sherman: Sharing Her Thoughts on Overcoming Dating Challenges, Overanalyzing Men and Much More

Interview with Amy Sherman

1. Can you talk about some of the most common dating challenges you hear from women who are in their 40s and beyond?

Anybody getting back in the dating world will find they encounter many challenges.  But for women over 40, the challenges are different. After all, things have changed since they were in their 20′s, when life was more carefree and simple.  

Here are a few of the most common concerns when entering the dating world.

1.  I’m not a size 4.  Will anyone be attracted to me?

If you think like this you need to do the inner work to get to a place of confidence and comfort with who you are.  There are many women who are not strikingly beautiful, long or lean and yet they are married to wonderful men who love who they are and how they look.  

Stop wasting your energy worrying about looking different and start being different!  Radiate the essence of who you really are and you will start attracting smart, relationship-minded men who are looking for a sharp, compassionate, fun-loving person like you!

2. How do I meet singles around my age?

You have to put yourself out there, especially in places that are of interest to you — classes, sporting events, book stores, political organizations, gyms and clubs.  Once you’re with people, start up a conversation by asking a question, offering an opinion or seeking some kind of help.  

Be sure to make eye contact, smile and show you are interested in the conversation. You can do that by paraphrasing what’s being said and by keeping your body language open and receptive.  Remember, nothing gained, nothing lost if you don’t meet someone.  At the very least, you are socializing and honing your skills!

3. I can’t seem to get past first dates.  What am I doing wrong?

You must be doing or saying something that is turning off your dates.  See if any of these ring true for you:

a. Are you coming across too needy or desperate? That would cause your partner to find you unappealing or intimidating.

b.  Are you talking too much?  It’s always a good idea to limit your responses and be a good listener so you don’t dominate the entire conversation.

c. As a woman, are you offering to pay your way too soon?  As a man, are you expecting a woman to pay her own way? Most men feel they want to be in control of the first date and like being generous and chivalrous.

d. Are you picking a partner who isn’t the right “fit” for you?

e. Are you sending negative vibes about what you don’t like about him/her — and your partner senses it?

f.  Is your voice tone or body language cold or stand-offish?

g. Are you overstepping healthy physical or verbal boundaries without realizing it?

h. Are you sharing too much about yourself and not leaving anything to your date’s imagination?

i. Are you too negative, cynical or sarcastic about dating and relationships and letting that come across?

4. Why do I keep attracting the same type of person into my life?

Many women do this because they gravitate towards what they are used to and feels most comfortable.  If you are used to dating dominating men, for example, a quiet, mellow man may not be someone you find attractive.  

Without realizing it, your choices become an unconscious habit that is difficult to break without some degree of awareness.  Therefore, if you find yourself dating the same type of person over and over again, you need to step outside the box and try something – and someone –new.  

Avoid the macho man and the “players.” Allow those with a more sensitive and caring nature to sweep you off your feet.  Then see how the relationship goes.  You’ll finally be breaking a pattern that may not be the best fit for a long-term relationship.

2. I think you covered the same major concerns that we hear from our subscribers. What would your advice be for women who are looking to get married fairly quickly and want to start a family because they are wary of a ticking biological clock? One of the problems we hear from these women is that they are not able to find enough marriage ready men.

When they do discuss marriage with men, they hear something along the lines like, “Yes, I do want to get married someday” or “Maybe, sometime in the future”. So this creates a situation where the woman may really like the man and he may like her too but they have two different timelines towards serious commitment and marriage.

Can you share your thoughts on how women can overcome this problem?

In the beginning of a relationship, you won’t know if the two of you are on the same page, but as you get to know someone and your conversation becomes more intimate and personal, the question should come up.

Naturally, the sooner you know their intention, the better it is for you. You do not want to waste your time with someone whose long-term goal is out of sync with yours. At some point, you need to stop second-guessing the relationship and find out what your partner truly wants. Don’t assume anything.

Ultimately, people are attracted to confident, self-assured individuals.

If you approach dating from a place of insecurity, fear or desperation, it will project to everyone you meet. A healthy woman does not look for someone to rescue her from her time clock. To attract the kind of person you want, you have to come across as a desirable, self-confidant individual, and that involves doing the inner work to get there.

If your insecurities are substantial and your fears of getting old are obvious, get private counseling before starting on the road to dating. If what you need is a spirit boost, look yourself in the mirror and acknowledge all your desirable qualities. Start believing in yourself and knowing that there is someone out there who will appreciate who you are and is ready to jump at making a commitment.

Become aware of your self-talk.

Catch yourself putting yourself down, calling yourself an old maid, washed up or undesirable or any other term you may have previously used to make yourself feel less valuable to the world. Start consciously calling yourself “a great catch,” and begin visualizing yourself laughing and walking hand-in-hand with someone special.

Keep mentally affirming, “I deserve a great mate, and I’m attracting him into my life,” or some other phrase that resonates with you. Start anticipating success and feeling like the person you want to be. Know you deserve to share your life and special attributes with some other very lucky person — because you found each other!

3. Can you talk about the importance of chemistry for a relationship to succeed long term and if women don’t quite feel chemistry right away, can it grow over time?

The truth is: Chemistry is important but it is not the “end all/be all” solution to all relationships.

Chemistry is usually there at the beginning of a relationship to keep you interested. You feel a physical attraction, a yearning, a sense that there is a connection that you want to pursue. It is an emotional desire to keep the relationship going and a physical magnetism to keep the romance flowing. Once you get to know someone, the chemistry remains, but what lasts even longer is the committed, emotional love that makes all healthy relationships worthwhile.

Remember that no one is perfect and that your mythical “soul mate” may not even have the chemistry you are looking for. However, you can create a happy, fulfilling relationship with many good partners. Choose one and give it your all!

Can chemistry happen over time? Here are some tips to see if that is possible:

1. You can grow to love someone as you get to know them.

This means that you will find them more attractive as you understand who they are, how they act and what they mean to you. The relationship becomes based on more than the physical, but instead is focused on the emotional, mental, intellectual and spiritual qualities that are even more important to you.

Things like respect, understanding, effective communication and the ability to forgive are very attractive qualities and will keep a relationship thriving and long-lasting.

2. If you’re forcing the relationship, you wont create chemistry.

Searching for chemistry in a relationship is touch and go. You may be able to find it eventually, but you also may be looking in the wrong place. If you and your partner are not sharing common values, goals, beliefs and interests, it doesn’t matter how attractive you are physically. It just won’t work long-term.

3. Relationships take a lot of work, compromise, respect and rapport.

There needs to be a sense of comfortableness, an opportunity to be authentic and at your best. The stakes are high when you give yourself to someone else and the incredible emotional connection is unmistakable. But, if it feels “right” even when it seems “wrong,” you are basing your relationship solely on an exaggeration of chemistry at work.

Your goal is to create a healthy, mutually satisfying relationship where you both are emotionally available, sexually attracted and growing together as you forge ahead. With this foundation, you are fundamentally on the road to a happy, healthy, compatible partnership.

4. What are the red flags that you would recommend women pay attention to especially when they are just getting to know the man. One problem that we hear is that sometimes women are so blinded by chemistry and passion that they either ignore or minimize or think that they would be able to change the man with their love.

How can women overcome this problem?

Nobody deserves to be in a bad relationship, but it happens.

Sometimes, you don’t realize it until it’s too late. Personalities clash, philosophies differ, values change and interests are no longer compatible.

But even through it all, there are some red flags” to be aware of so that you don’t get caught making the same mistakes over and over again in another relationship.

1. Avoid anyone who comes on too strong, claiming he/she has “never met anyone like you” and pressures you into an exclusive relationship early on. This dynamic can easily “suck you in” causing you to ignore the dangers of this hyper-charismatic personality.

2. Avoid anyone who is excessively possessive, calls constantly or visits unexpectedly. It may seem attractive, at first, but a healthy relationship allows you to have your own life, interests, and outside friends without feeling guilty or intimidated.

3. Avoid anyone who interrogates you about people you talk to, where you go, how much money you spend, etc. Again, this possessive nature is not only unfair, but it is controlling.

4. Avoid anyone who blames others for his problems or things that go wrong. Be alert to individuals who don’t take responsibility for their own actions and find fault with everybody else.

5. Avoid anyone who is hypersensitive or easily insulted. If you have to walk on “egg shells” because you are fearful or uncomfortable speaking your mind, your relationship is one-sided.

6. Avoid anyone who is cruel to animals or makes demands on children beyond their ability. A person who is not empathetic to the pain or suffering they are inflicting on others can be emotionally and physically dangerous.

7. Avoid anyone who uses “playful” force during sex. If there is no regard for your comfort or concerns, this individual is only caring about himself and his own needs.

8. Avoid anyone who is consistently critical, degrading, nasty, argumentative or moody. Emotional abusive people instill fear, insecurity and doubt in the person receiving the abuse and can destroy the self-esteem of the victim.

9. Avoid anyone with a history of past physical battering. A batterer usually will not change unless they’ve had some professional intervention.

10. Avoid anyone who makes you feel unsafe by being intimidating or threatening.

Your relationship needs to be safe, supportive, nurturing and respectful and if you “feel” otherwise, those indicators should not be ignored.

Women are often blinded by passion, chemistry, and charisma. While those are all wonderful and positive characteristics, just don’t discount other times when circumstances cause you to feel differently.

The healthiest intimate relationships are based on substance and you and your partner need to be sharing, growing, compromising and working together so the relationship keeps blossoming.

5. A problem that we commonly hear from highly successful professional women is that they tend to exude masculine energy that is largely responsible for their success in their careers but they find it difficult to transition to feminine energy in the dating world.

What advice do you have for women who struggle with this problem?

Being single certainly has its perks.

You can do what you want, when you want, the way you want to do it. There’s no one directing, controlling or leaning on you – either physically or emotionally. And for many independent singles, that’s just the way they like it!

However, sometimes these independent singles have high powered, leadership jobs that create an energy and lifestyle that could be intimidating, even too masculine – leaving no room for anyone else to enter. There’s an emotional wall that hinders others from sharing and this energy flashes a “keep out” sign across their forehead pushing others away or making them feel unwelcome.

If this description sounds like you and you keep saying you want to find a rewarding relationship but there’s no one out there, the answer may be simple: your job and lifestyle make it difficult to be the warm, fuzzy, feminine and inviting individual you really are – and you are ready to change all that.

We all know that being in a relationship means you are not just you alone anymore.

You’re expected to compromise, to be flexible, to explore life’s activities together. To play a part in a relationship, you’re expected to be a partner – and to make your partner feel special. For some folks this is more of an impediment than they want to accept – even if they won’t admit it.

Happily, if you are aware of this, you have options.

You need to work on maintaining your independence while in a relationship, yet also making sure there is a balance – a give and take soft, nurturing side– that is healthy and acceptable.

For many, finding another independent type is a good option. They can complement you without smothering and they will also understand your need to be in charge when it feels right. However, you need to let go and allow others to lead as well, as that is what a healthy relationship calls for. Steer clear of needy, co-dependent types. They’ll feed your nightmares and will likely overwhelm you with “togetherness” when that’s the last thing you’re looking for.

Rather than giving up on a relationship, look for a comfortable fit for your personality type and create the relationship parameters that best fit YOU. You’ll get the best of both worlds – and be better for it!

6. Some of the common dating problems we hear from women are “He said he would call, but he didn’t”, “I feel like I am doing most of the work in the relationship”, “I am not sure where we stand in our relationship”, “Things were going so well and suddenly he pulled away” etc.

A lot of times, women tend to worry a lot and excessively over-analyze why the man is behaving the way he does. However they fear discussing these issues with him because of the fear of losing him. What would your advice be for women dealing with these problems?

This question reminds me of a joke I once heard.

A woman was telling her friend her side of what happened last night. Her boyfriend didn’t call and the night before he was in an odd mood, causing her to think she did something wrong. She said it may be her fault because she was a bit later than she promised, but it could be something else.

Later that night, she told him how much she loved him and all he did was put his arm around her. When they went to bed that night, they made love, but things felt different. Woman said she doesn’t know what to do and that he may be seeing someone else.

The guy was telling his friend his side of the story. He said the Cowboys lost, but he got laid, though.

Women tend to over-analyze situations, creating scenarios that are overblown stories, created in their heads.

This doesn’t mean that what they are feeling or seeing is not true, but it also means that she shouldn’t assume things without getting all the facts. The best advice is to communicate to get clarity. Had she asked her boyfriend why he’s in a peculiar mood, he may have told her he was down because his sports team lost. But jumping to the conclusion that there’s something going on makes her “crazy” with uncertainty and unanswered questions.

John Gray, the author of “Men Are From Mars, Women Are From Venus,” says that men and women need to understand each other’s needs and wants (caring, validation, appreciation and reassurance) or else there will be frustration and difficulties.

So, to understand your partner’s primary needs, you have to learn to listen, being aware of gender differences and communication styles.

With this greater awareness, you can eliminate the pitfalls that sabotage most relationships and instead focus your attention on what your partner most desires and craves from you.

7. On the other end of the scale, some women face the opposite problem whereby they ignore the red flags and set no boundaries in their relationships. As a result they find themselves in unfulfilling relationships and they stay because they are either too scared to be alone or they hope the man would change some day. However that seldom happens.

Can you talk about the importance of setting proper boundaries in relationships and how do you recommend women set boundaries especially for those who have never set them?

Many singles know how to respect limits.

They understand when they become too intrusive and are aware when they are being too invasive. They pay close attention to the cues from others and are able to maintain a healthy balance in their relationships and interactions with other individuals. They are also willing to make the necessary changes so that their relationships remain strong, vibrant and equal.

However, sometimes people are not so intuitive. Especially with the men you date, there needs to be some guidelines that you follow so you don’t continue to get hurt or feel compromised by your partner’s behaviors.

Here is how you can handle things in the future.

1. The purpose of setting boundaries is to protect yourself from people who can be abusive, inconsiderate or clueless.

2. By stating your feelings, you let others know that your rights have been overstepped and that you are taking responsibility for how you feel and what you need from them.

3. It is easier to set boundaries and assert yourself with people with whom you don’t have strong relationships. It becomes more difficult, but even more necessary, with those you care most about.

4. Remind yourself that you deserve to be treated with respect and dignity and that it is vital if you are to love yourself. Therefore, you feel comfortable revealing to others unacceptable behavior and the changes you will like them to make.

When you set a boundary, you also have to let go of the outcome.

This is because some people are incapable of changing. It is their choice to refuse to make things better. Then it is your choice whether you are willing to stay in this situation. Just remember that how others treat you is based on how strong or weak your boundaries are.

Your personal boundaries define the edges of your physical and emotional space.

Pick and choose the most important behaviors that need to be discussed and then state your request. Hopefully, the men you care about will be willing to make the necessary improvements to keep your relationships honest, respectful and mutually satisfying.

8. Some of our subscribers aren’t quite sure whether they should stay or end their current relationship. Do you have any guidelines regarding when it is worth staying in a relationship and work things out and when it is better to end it?

Should you stay or should you go?  That is an important, yet confusing question. Ideally, you would want to be with someone who is considerate, kind, sensitive, emotionally stable and supportive. If you throw in romantic, affectionate, funny, attractive, healthy and intelligent, you have it made!

Realistically, relationships have some of these qualities.  You may have to give up a few, but if you recognize that you already have what’s most important to you, you are very lucky.

There are three factors to consider when you are assessing whether your relationship is a good one and worth working on.  They are:

1. A good relationship will possess what you consider your “must-have” necessities

In other words, you share the same religion, same philosophy of life, same political affiliation, same level of commitment or same moral values.  These are things you find very important and ultimately give your relationship a solid foundation.

2. A good relationship also has some flexibility, which means you can each be who you are

You love Chinese food, but your partner hates it.  You love listening to jazz and your partner doesn’t understand it.  You read inspirational books and your partner likes mysteries. Obviously, it’s OK to be different and this in fact makes the relationship more exciting.  It also makes you more tolerant and respectful of different perspectives and opinions.

3. A good relationship makes concessions

You’ll agree to watch a war movie with your partner and your partner will agree to go to the ballet with you. You’ll learn golf and your partner will take dance lessons.  You’ll sit through the Super Bowl and your partner will watch Sex and the City reruns.  These compromises show that you care and that “bending” is more important than winning a fight.

In other words, your relationship is really good if you allow each other to be who you are, yet are flexible enough to step out of your box to explore each other’s interests

Evaluate how much significance you place on each of the three factors above and see if some of those more rigid necessities can be made more flexible. As you work on compromising, listening and sharing, your relationship should grow.  If it isn’t growing, it may be time to move on.  Cooperation, negotiation, adaptation and conciliation are all essential tools for keeping the relationship healthy and long lasting.

9. Can you share your top 3 tips that can help women create better connection and commitment in their current relationships?

1. Don’t Be a Martyr

Do not be a martyr, sacrificing yourself of behalf of your new love. Take care of yourself, above all else, to ensure you maintain your health and well-being.

You should never feel guilty about focusing attention on yourself and your personal needs. Continuously nurture yourself through your self-talk by repeating approving messages of support and encouragement. Your personal internal dialogue should reflect your belief that you’re doing well and deserve the best in life.

Say things like, “I am doing and feeling well,” “I deserve to be happy,” or “I love life and will continue to enjoy myself daily.” This kind of dialogue will keep you focused on yourself, something too many women forget to do when in a relationship.

Continue following your daily routines.

If eating out often, for example, does not make you feel comfortable (for health or weight reasons), but it is something he prefers, don’t sabotage yourself to please him. That is the opposite of empowerment. Consider your health and self-image. No relationship is worth disrupting your life and your well-being. The best thing to do is be flexible whenever possible, but always maintain the values that are very important to you.

While compromise is an important quality in successful communication skills, never compromise who you are for the sake of anyone else.

Keep your integrity and the standards that you live by, so you won’t feel put upon or diminished by a new partner. Honor yourself by thinking independently and enjoying your own perceptions and opinions. Live authentically, speaking and acting from your own convictions and values.

None of this should be confused with being “selfish,” thoughtless or uncaring with your relationship partner, family or others. It doesn’t give you license to mistreat or be insensitive to people. The message above is about honoring yourself fully. But it should never be an excuse for bullying or abusive behavior.

2. Remember Your Four Basic Rights

Always remember you have rights. You, your partner and everyone else, all deserve the same things. They are:

1. The right to think what you think
2. The right to feel what you feel
3. The right to want what you want
4. The right to say NO

When you say NO to something that doesn’t feel right, you are saying YES to acknowledging yourself and letting in a more loving, supportive experience.

But remember, if you have the right to an opinion, so does your partner. That means, through mutual respect and understanding, you can avoid the arguments associated with trying to change someone else’s mind or make them behave differently.

Your life is yours to control.

Work on managing your challenges with skills that help you overcome obstacles and bounce back from adversity. The way you do this is by expecting things to turn out well, by staying calm in the face of turmoil, and by keeping your focus on healthy solutions and actions.

When you’re in control of your life, you are free to implement the most effective coping skills and management strategies. These decisions will result in better choices and more successful outcomes for you.

3. Watch Your Expectations

The relationship you have with your partner is special. Your partner is there to grow with you and to share in your life. However, if you expect too much from someone or put too high an expectation on someone else’s role, you are setting yourself up for failure. In other words, don’t rely on a fantasy to fulfill what you desire.

Be sure to openly discuss long-term expectations.

Opposites don’t really attract if your value systems are not in synch. For example, are you a homebody, satisfied to stay inside to read or watch TV while he is the social butterfly, always looking for friendly get-togethers? Are you attached to frequently spending time with your family, while he has little interest in promoting family outings? Differences such as these build up to become major issues if not addressed early on and accepted with grace.

Smart women understand the value of discussing their expectations to be sure you both have the same intent, values and goals. When you know where someone is coming from, you will be less likely to misinterpret their actions or behaviors and, therefore, not be disappointed.

10. What books or resources would you recommend for women that are looking to create long lasting fulfilling relationships?

Dating Rescue! 10-week eCourse for Women

This powerful 10-week eCourse will have you dating smarter, feeling more empowered and having more fun! That’s because in each Transformation Module you’ll find some of the most important advice and dating strategies available anywhere for women of all ages! You’ll get answers, advice and solutions to all your dating frustrations.

The 10-module format is easy to access, easy to digest and easy to implement … so you can attract and create the meaningful relationship you are looking for! You learn everything from how to realistically begin a romantic relationship … through the strategies for developing a healthy, mutually satisfactory bond with a potential significant other … and lots more!


Dating After 40: Create Your Ideal Relationship Kit Everything you need to attract the right love partner!

Within this Kit you’ll find strategies, advice and tips you need to know about before dating, while dating, when entering into a romantic relationship and when deciding whether you’ve found a “keeper.” You get five valuable resources, each one created to enhance your dating skills and radar while building your intuitive sense of personal empowerment.

The Kit’s Dating book, Coaching Seminar CD, Assessment Guide, Communication Skills ebook and Transformation Journal were designed to complement one another … working together to boost your strengths and firm up your weaker assets. It’s a winning combination that gives you a competitive edge that has nothing to do with looks, weight, background, finances or other self-sabotaging beliefs.

And all the tools, tips and techniques are easy to access and implement in one comprehensive Kit!


99 Things Women Wish They Knew Before Dating After 40, 50 and Yes, 60!

This book targets you, women aged 40, 50, 60 and beyond – the Baby Boomer generation. You are the dynamic, active women re-entering the dating world in mid-life with challenges and baggage vastly different from in your younger years. You don’t want to waste time and do want sound advice from experts you can trust and relate to. In fact, the content is so relevant, women of all ages will benefit from the powerful wisdom and valuable techniques.

This step-by-step guide will have you dating smarter, feeling more empowered and having more fun. Why keep kissing frogs — when “99 Things Women Wish They Knew Before Dating After 40, 50 & Yes, 60!” will show you the way to confidently attract the “prince” you’ve always been looking for.

Available on Amazon and Barnes and Nobel, digital or paperback.

About Amy Sherman

Amy Sherman

Amy Sherman, LMHC, is a licensed mental health counselor in the state of Florida, with a master’s degree in Counseling/Psychology from Vermont College.

She has over 13 years experience in the field and has worked with adolescent substance abusers, abused men, women and children, patients with severe mental illness and the elderly.

To know more about Amy, visit her website www.yourbabyboomersnetwork.com.

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