Rich Midlife Bachelor Cannot Find Love

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[You might also want to check out the article here on entitled, How to Date the Wealthy]

As I approach my 52nd birthday, I find myself a never married man with no prospects. Most of my relationships have lasted one to three dates over my entire life, and many of the women that I have had sex with were brief encounters (one night stands, not prostitutes). I was engaged once, but she had a problem with alcohol that ruined things. It seems that the women that I wanted a long term relationship with the most were not interested in more than friendship with me. The women that were most interested in me, were either not very attractive or had way too many problems and drama in their lives. Now, I know that attraction is not the only criteria for a successful relationship, but if I am not attracted to a woman, then I can’t see a future with that woman, other than friendship. I have however felt strong feelings for a few women that most would not consider very attractive. They too liked keeping me as a friend. I think that when someone tells you that they want you as a friend instead of a mate or lover, it means that they are not attracted to you sexually.


At this age, I find that most single women I see would consider themselves too young for me. I am reluctant to ask out women that are obviously twenty or thirty years younger even if they seem slightly interested even if I really want to ask them out because I don’t want to be embarrassed at their reaction at the age difference. I’ve had a couple women to agree to go out only to cancel when they found out my age.

I recently retired after selling my business and am financially set and live well. That has not yet seemed to attract any female attention either. I always heard that if you had money that you would get the ladies. Well, I became a millionaire and it hasn’t helped so far. I look about 40 I am told and I consider myself a decent looking guy. Women closer to my own age are often grandmothers and even if they are unmarried (divorced), we don’t seem to have much in common and they don’t seem to have much interest in me either. They may notice that my eye tends to be drawn to younger women. I do find some older women attractive but almost all are taken. I have all but given up by only asking out a few women over the last ten years, but I do still hope for love, companionship and intimacy. Any suggestions?


First of all – congratulations! You have done well for yourself … sold your business … are financially in great shape … that is AWESOME … particularly for this day and age. I’m sure that you appreciate your good fortune and success, and so if you are bothered by anything else, then KNOW that you do have your security.

As far as women go – my best advice for you is that you get your numbers up … which means make a proactive effort to meet a lot of women. What is “a lot of women”, or how many is that? The answer is – it is all relative. I’d suggest using eharmony or chemistry (visit our Online Dating Promotional Codes and Links page for some great trial offers) or any of the various dating sites to help get yourself out there. The more you meet in person, the better your chances of landing a good relationship. And sometimes it can take TIME … a lot of time.

It can also depend on how you present and project yourself toward women. Hopefully you found the Midlife Dating Advice section of If not, there are some good article there to check out – even if as a sanity check or reference:

1) Midlife Bachelor Personal Makeover

2) Develop a Strategy for Midlife Bachelor Success

Since you said you are a young-looking 52, then I’d suggest that you focus on women in their early 40s. You can try for 30s, too – if you can pull that off. But the main thing is – you have to put yourself out there ANY WAY YOU CAN and meet women who are available. I’d suggest the online dating sites, plus you could try local activities of interest … and/or maybe network through female friends of yours, etc. Online is easiest though.

You should also consider joining our Midlife Forum here on – where men and women our age discuss various issues, including issues like yours.

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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.