Dating Advice #273 - Highly Inexperienced


At age 36 he's just breaking out of his social shell. Is he doomed to dating failure?

Dear Rosie & Sherry,

I am a 36-year-old man and have never been involved in any serious dating. The few times I've had dated have not gone well. I fear that my chances of being married and having children are almost nil.

How did it get to this point? I was an unpopular kid in high school, getting picked on constantly and not fitting in. The only friends I had were other unpopular kids who were isolated from the mainstream. The pattern continued in college. I was a nerd without the academic ability -- a terrible combination. I also have a learning disability (which affects me socially) that wasn't diagnosed until I was 28.

Due to my poor social skills, I had trouble getting along with co-workers and bosses.

I thought that once I got into the work world, things would change. But alas, I had tremendous problems getting and keeping a job. The only jobs I could get were almost always temporary positions. The longest I held a job for was two years, but often I got let go after only a few months. Due to my poor social skills, I had trouble getting along with co-workers and bosses. Things got so bad that I moved to a different city in the hopes of a fresh start.

Things did improve for me. I finally have success in a job and am making as much money as the average person. My social skills have improved to the point that I can "get by" in some social situations, although I still bomb in large group situations. And I have a better idea of what has been holding me back in the past.

I now believe I am finally ready to date. The problem is I am 20 years behind everyone else in terms of experience. How am I going to catch up? In addition, a high percentage of women close to my age are married or divorced.

Is it too late for me to start now? My big worry is that women will shy away from me because of my lack of experience. They will think "Why hasn't anyone wanted you?"

Should I admit my lack of dating experience to the women I date, or should I try to hide it?

I need advice on what to do going forward. I do not want to be single my whole life.


Dear Lenny,

We are impressed by your perseverance. Many people whose life experiences are similar to yours give up on themselves, and get locked into a life of disappointment and under-achievement. Not only did you not give up, but you pushed yourself to learn from your career mistakes and find a job that was a good match for you, move to a city that was more compatible with your own personal style, and work on your social skills so that you could relate better to people. In addition, you're making a conscious effort to identify areas in which you can grow, and to work on that growth. Your character strengths and your willingness to grow are very admirable personal qualities and are great assets for a marriage.

The first issue we'd like to address is your self-esteem. Often, a child who was teased and made fun of carries into adulthood those painful feelings of humiliation, inadequacy, and not fitting in. An adult who has worked hard to address these feelings and to believe in himself, as you have done, can nevertheless experience periodic episodes of self-doubt and personal disappointment.

A dating coach is necessary for anyone who doubts their ability to date successfully.

This can be especially true when it comes to dating, which in itself can be an ego-destroying experience even for men and women who grew up with strong feelings of self-worth. A dating coach or dating mentor, who is an invaluable source of emotional support, encouragement and advice for any dater, is practically a necessity for anyone who harbors doubts about their own ability to date successfully and build a relationship that will lead to marriage.

People experience many possible sources of these doubts -- due to scorn, rejection, being teased or bullied by childhood peers, academic struggles because of learning disabilities, an inability to fit in because of poorly developed social skills, receiving criticism from parents, or years of unproductive dating.

As you get ready to date, we also suggest that you ask yourself if therapy might be beneficial. It seems that you have come very far in addressing the difficulties you had growing up, and it may very well be that a therapist has helped guide you through this process. However, if you regularly have deep feelings of self-doubt and inadequacy, we recommend that you work with a therapist to help you continue to gain a more positive self-image.

We've met many daters who are so plagued with doubts about their self-worth that they can't allow themselves to succeed in relationships. They wonder what the other person sees in them, are afraid that the other person will reject them when they "finally see the real me." They tell themselves that only a real misfit could even be interested in them, or seek out dysfunctional dating partners because "nobody decent will ever want me."


The fact that you're getting a late start on dating should not be a reason to doubt yourself. Plenty of people begin dating a little later in life than others. There are many reasons for this. Someone may not be emotionally ready for marriage until later in adulthood. Others date casually for a long time until they decide that they want to focus on developing a meaningful relationship that will lead to marriage. They may begin their adult lives in a location where there are few Jewish men or women to date. They may have to resolve any of a number of personal issues. Or like you, they may be late bloomers in life, who take a little longer to come into their own.

Many late-to-start daters have found that they can catch up on their lack of dating experience quickly and go on to meet the right person. In fact, they often have an advantage over other unmarried people their own age. How so? Because they are focused, sincere, and not ashamed to ask for guidance. They're open to learning how to choose dating partners who have spouse potential and how to date in a way that builds a lasting relationship. And the people they date, for the most part, won't be concerned about how long they've been dating -- they'll be focused on who they are, where they are going in life, and whether they are right for each other. Remember this focal point - that your goal is to build a meaningful, enduring relationship. It will help keep you centered.

Get a Coach

It's understandable for you to be concerned about having the social skills to be able to relate to a woman you're dating. We've found that the acquisition of social skills is a little like learning to use a computer. Some people seem to have an innate ability to figure out how to use computer programs, just as some people seem to have a natural ability to relate to others. The vast majority of the population can become computer-literate after they receive a small amount of instruction and observe people with computer know-how, just as most people develop social skills by getting advice from parents, teachers, or peers and by modeling how they see others behave.

The rest of the population may believe they are either technologically challenged or socially challenged, but it is usually just a matter of needing to learn these skills differently. They may benefit from more intensive instruction that other people, but eventually they pick up on the basics. And because of the learning curve, once they attain basic competency, they find it less and less difficult to become proficient.

You may need pointers on dating etiquette and how to keep a conversation running.

This is another area in which a little bit of coaching can go a long way. Instead of struggling through your first several dates, agonizing over whether you're doing things correctly and wondering how you can ever be yourself when you're so anxious, find a coach to help you prepare for dating. You may need pointers on dating etiquette, what to talk about, how to listen to and show interest in your date, how to keep a conversation running, the best ways to pace a date, and how to relieve any anxiety you may be feeling.

A coach may role-play dates with you, help you decide what to talk about or do on a date, listen to your concerns about what might happen, and encourage you to develop strategies to deal with these "what ifs." Eventually, you'll be able to handle these aspects of dating on your own.

Who can play this role in your life? You may know of someone who is happily married, has good judgment and discretion, and is willing to make the time and effort to become your dating mentor. Or, you may want to use the services of a professional dating coach or life coach. Ask about their training and experience in helping people with social skills and with building and sustaining relationships.

Telling the Past

You asked whether you should tell a woman you are dating about your lack of experience. It's not necessary. She also doesn't need to know that you were a nerdy kid, that you struggled with an undiagnosed learning disability, or that it took you a while to realize your potential. Painful subjects like these aren't good topics for anyone to discuss during the early stages of courtship.

People sometimes mistakenly ask the "wrong" questions on a date. If your date asks about your dating history or your past relationships (these should be taboo topics during the first several dates, because every answer takes the daters' focus off of each other), we recommend saying that you'd prefer to talk about what's going on in each of your lives now. Have a couple of different subjects in mind that you can easily steer the conversation toward.

Your date may ask why you aren't married yet. Instead of the safe but meaningless answer of, "I haven't meant the right person yet," why not tell her that you spent a lot of time developing yourself and your career, and only recently became determined to focus on finding the right woman to marry.

There will be time, in the future, for you to reveal some of the painful aspects of your social history to a woman you are dating. When you reach a point in a courtship that you feel a strong sense of friendship and trust, the woman will be more receptive to hearing some of the difficulties you overcame in your journey to become the person you are. That's when it may be appropriate to talk about your childhood, teens and early adulthood -- and how you overcame these challenges and worked to develop and refine your character and personal strengths.

Finally, we'd like to offer an unsolicited suggestion that we believe will help you start your dating career on the right foot. We have found that daters who feel good about how they look, also feel good about themselves and project a positive energy that appeals to others. That energy can make all of the difference in the world, because people are attracted to someone who thinks positively about themselves.

It's important that you think, "I care enough about you to make a good impression."

In addition, someone who has taken care of his appearance gives his dating partner a message that, "I care enough about you to make a good impression. I want to look good for you and I want you to feel comfortable when you are with me."

For these reasons, you may want to meet with a style or image consultant before you start dating. She'll give you pointers on how to maximize your appearance with an attractive haircut, grooming, and stylish, flattering clothes that suit your taste. Why not enhance the real you and feel good about yourself? It is a small investment that can pay enormous dividends.

It seems to us that your hard work on developing yourself, and your courage in writing to us, is the sign of a man who is ready to invest the time and effort to meet the right woman and have a wonderful lifelong marriage.

We wish you success in navigating the dating maze,

Rosie & Sherry

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