Lonely Boomer Guy Seeks Compatible (younger) Women

Dear Dating Coach,

I'm a 48 year old, heterosexual male who has been divorced about seven years. I have no children. Even though my divorce was emotionally painful for me, I believed at that time that I would have an easy transition back to my old single (and dating) life, and that my sadness would soon be over. A few short lived relationships with younger women followed fairly quickly, but none of them lasted longer than a few months. All said they had enjoyed their time with me, yet in the end they found younger men to settle with.

For the past two years I have been living dateless and in celibacy. I'm beginning to experience a kind of desperation, due to my fear that I'll never be able to find a woman again with whom I could enjoy sex, love and intimacy. I have heard many women talk about how getting older is much easier for men, but in my opinion, this is only true for men who are wealthy, very successful in their careers, influential/famous, charismatic and/or handsome. Unfortunately this is not me. I am a slightly built, light skinned, baby faced, balding teacher, and not exactly a classic woman's dream. I get along very well with women and have many women friends (a number of them single). They appreciate my humor, intelligence and understanding nature, yet it is rare occurrence when one of them shows an attraction towards me.

Many of the women I come into contact with are married, very successful and affluent and looking for the same and/or living a complicated life (problem kids, money problems, angry ex spouse, no longer attractive, boring, etc.). I avoid these situations as my work is draining enough and I don't want these problems coming into my life. The women who would be a better fit for me tend to be spiritual, vegetarian, artistic, open-minded, easy-going, and about 20 years younger than I am. I would like to meet a woman close to my age, who has these qualities, but find it almost impossible to do so.

I've tried online dating but found it to be a flop, and can't afford the services of dating agencies. I also don't feel confident relating virtually to someone I have not yet met in a face to face situation. Then there's my reluctance to post a photo, as I know that my strengths are my personality and intelligence, and my physical appearance will work against me.

Is it possible for a man my age (48) to successfully find a lasting relationship with a woman who is about 20 years younger? If not, where and how could I find women closer to my age that are single, compatible, and who could be interested in me? --Boomer Dater or Bust

Dear Boomer Dater or Bust--

What stands out in your email is the negative picture you paint of yourself, your career, and the available women in your age group. I wonder how your beliefs, and how you may be projecting them, could be impacting your search for Ms. Right. Is it possible that you are experiencing some depression, perhaps brought on by frustration and loneliness?

What I am about to say may be obvious, but I will say it anyway. There are lots of guys out there who don't fit the classic image of handsome--yet they have no problem attracting women with the strength of their personalities, their charm and a healthy measure of positive self-esteem. Knowing this leads me to suspect that you may be projecting a low self-esteem, and this is a turn-off to women (and men).

Let me also say (for the record) that there are plenty of great single females who are not looking for wealthy or high status men. They just want to find one good guy that they have the right chemistry with. I have talked to these women and have heard their frustration. By the way, they are not unattractive, gossipy, overburdened, etc. No woman comes without any baggage, just as you do not. You asked about meeting women 20 years younger, and I wonder what is wrong with all those great never married, childless women in their mid to late 30's or early 40's. They ARE out there. Granted, you may have difficulty meeting them at work, but what about in your community, through adult sports leagues, volunteering, community boards and special functions and/or all the other resources must be available around you, regardless of your geographic location?

You must have some interests or passions that you would like to get more deeply involved in. This is a great way to meet like-minded people. There are also niche dating sites for vegetarians and people with other special interests or lifestyle concerns. It takes a little willingness to go beyond your comfort zone, but it's worth it, don't you agree? You could address some of your self-esteem issues by starting a work out routine--it does not have to cost a lot or take up too much time. If you feel you are too thin or would like to get more tuned, this is something you can work on. There might be other image things you could do to address your desires to enhance your looks and play up your good features. You have them, I am sure, despite your assertions to the contrary.

If depression is an issue, get some help for this as well. I'm sure your insurance covers therapy visits--and the right male therapist might be just what you need to help you address some deeper issues and encourage and support you in making positive changes. We all have choices, no matter what life hands us. Before you give up and your whole world gets "painted black," come up with some easy objectives to address personal issues, body image, where you could meet compatible women, and anything else that may be standing between you and what you want.

Here's an article I wrote on the topic of meeting people, maybe you will find it helpful:

(from August 2007)

Want to read other columns on this subject?

"Handling red Flags in Dating"
List of more
"Compatibility Issues"

"A Place in His Heart- or Holding a Place for Someone Else?"


Toni Coleman, LCSW
Phone: 703-847-1768


Copyright 2008-2015 Antoinette Coleman. All rights reserved.

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