Man Wants Girlfriend 20+ Years Younger (don’t we all?)

People write in to ASK MIDLIFE BACHELOR with questions.  An index of all Q&As is located on the ASK MIDLIFE BACHELOR INDEX page. Email your question in complete confidence to [email protected].


I am a 60 year old white male who is just now trying to get back into the social scene after a nearly 20 year hiatus. My last relationship ended in 1991 when my then fiancé gave me my pink slip. I lived with her and her two children for eight years and was her de facto husband and the children’s de facto father. It seems that in truth I was really just a cash cow for the deadbeat sperm donor father of her children. After the son left to live on his own, and the daughter was a year from graduating from high school, the mother cut me loose, I was just 42 years old. She found someone with deeper pockets. Hurt, and with a mountain of debt that she had charged on my credit cards, I left and went into a depression that only deepened with the recession that was just beginning to take hold. I was destroyed emotionally and financially. It was bad, very bad. I lasted 11 months in my new apartment and had to leave because I could no longer afford the rent and all the bills. For the next 10 years I lived a hand to mouth existence and very nearly wound up having to sleep in my car. To say the least, I was not a good catch for any woman, and I knew it. I’ve had three long term (live-in) relationships in my life, but have never been married. But that’s a whole other tack. It’s


not that I didn’t not want to be. To quote Shakespeare, “I loved not wisely, but too well.” At this point in my life, these words would make a fitting epitaph for my grave stone.

All these years later I have rebounded from that awful episode in my life, but I’m 60 now and I have no place to go. All of the social venues are not for people of my age even though I am seeking a younger woman. My recent foray into membership at a personals site has met with no success. No one, it seems, is willing to even give me a chance. No, I’m not a movie star look-alike, but neither am I an ogre. I’m well educated, well read, classy, and cultured. From what I’ve seen in the personals ads I am severely height challenged being just 5′ 8″. But I’m slender and fit. No bald head, and no beer gut. I have manners and excellent social skills. All of my life I have owned the skills that a gentleman should have. I know well how to treat a lady, both in and out of bed. I give nothing away to younger men except years. And if I can no longer prevail in a footrace or other physical contests, I can prevail in all the ways that really make a man a real man.

Under the circumstances it may seem fanciful to hear me say this, but I am not interested in meeting post-menopausal women. I may be 60, but the truth is that I still have plenty of life left in me and I feel perfectly capable of meeting at least most of the need and desires of a younger woman. Someone 30-ish or 40-ish. I’m done with women who are looking for a free ride, who have intractable emotional issues, and previous relationship/divorce issues. In other words, unattached women who are my age contemporaries.

What is a man like me to do? Where can a man like me go to get honest introductions to younger women who would at least not dismiss me out of hand? I suppose I could go to one of the plethora of international mail-order bride sites but this is no answer. If you have any, and I mean ANY advice for me, please reply.

MIDLIFE BACHELOR ANSWER: Thanks for writing in. You know – you are in a somewhat similar boat to someone who wrote in recently – and much of what I told him also applies to you, so please check this other ASK MIDLIFE BACHELOR Q&A out:

Older Bachelor Needs a Cougar

Now you are different in several respects – at age 60, you are much older than the gentlemen who wrote in with that question, and much older than all of us here. Sounds like you want to raid the women in our age group though – and I definitely admire that!

In reading what you say you are and are not looking for – I notice that you are extremely exclusionary. For example, you don’t want anyone post-menopausal … you don’t want anyone looking for a free ride … you don’t want someone with emotional issues … nor anyone with baggage. Well to me it looks like you just excluded pretty much ALL women! I mean – even women in the 30s and 40s have at least one of those characteristics. [And so do most of us men, too!] So I think you might seek a form of perfection that does not exist. Remember – (and this is the second time I’ve used this saying today), there is what’s ideal, and there is what’s real … so my #1 piece of advice is to loosen up your criteria a bit ;o)

The core advice I have for you is identical to what I told the guy in the Older Bachelor Needs a Cougar article. The only thing I can add is that if you really insist on finding a woman in her 30s that your best bet is to use one of those mail order bride websites.

I mean you can also join and blanket all of the traditional online dating sites, and be persistent with respect to going after the 30s crowd … but really your only chance for success there will be if you find someone with a lower sense of self esteem … a woman who desperately needs someone to pay attention to her … and I’m not sure that someone like that would constitute an ideal girlfriend for anyone, right?

Concerning mail order brides – to my own horror at the time, one of my best friends went that route several years ago and got himself a Filipina bride … and one could make a case that he is now the happiest of any of us. Go figure! [I’d personally look toward Mexico or Brazil if I were to do something like that though.] Anyway – my buddy’s wife is happy because she has running water in the house, and plumbing … and my buddy is happy because he has a wife who is younger and better-looking than anyone he could possibly have attracted over here.

If I were you, I’d honestly go after more normal women between age 45 and 55 – and see what happens. Good luck to you!

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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.