Older Bachelor Needs a Cougar

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’m 54, and my first wife divorced me after 25 years of marriage. Dated a woman for 3 years, got married again, retired from my job, bought a house with her for cash in the state she lived and worked in, and moved there. All hell broke loose, and I filed for divorce and left after 8 months of trying to make it work. She was perimenopausal, into her career, and couldn’t afford to not spend any less time with her girlfriends. She told me that “Husbands come and go, but girlfriends are forever.” Well, I guess she was right. I told her that I was better off being alone then being lonely in my own house. The divorce becomes final in July. We obviously should’ve cooled our jets, and not gotten married nor bought a house together. She bought me out and I lost $12K because of the market drop.

I moved back to my former state but to a different town and started a business. I subscribed to an internet dating site which has proven to be a poor performer. Went out three times with a woman who told me she wanted to be “friends” and that she was “confused” after I kissed her. I laughed at her and told her that I hadn’t heard that since I was in high school. Needless to say, we don’t date anymore. I contacted a woman that I had known in


college thirty years previously living in another state … there had been chemistry then … as a lark and now it has gotten interesting. Lot’s of phone calls … emailed photos, etc. I have told her that before I do anything else, she needs to finish ending her marriage. I don’t even want to be part of that because I know what happens in rebounds. Plus I don’t want to get shot. But damn, she sure is cute.

Here are my problems:

1) I’m really horny, and desirous of female company. I just love being with women. They’re great.
2) The women that I have met who have indicated more then a passing interest in me (within my age range of 45-55) are really overweight or much older than I am … like in their 60’s. I know that this is limiting, but visually it just don’t do it for me – the fat or the wrinkles. Don’t get me wrong, I’ve got no hair on the top of my head, and it’s all gray.

I think I like the idea of cougars … in fact, I got nailed by a 37 year old divorcee when I was 24 one time. Hard body but a little crazy. However, I can’t get there from here with women who remind me of my mom.

I’m in really great shape because I do hard physical labor all day in my business and wear the same pant size I wore in basic training. Prior to that I was a dedicated gym rat for health reasons.

I have no debt, own two homes outright, have an excellent credit rating, and my medical is through the VA. No sports cars, no gold jewelry habits, but I do have a motorcycle and I sleep well at night. Got any advice or tips?

MIDLIFE BACHELOR ANSWER:  Thanks for writing in – and yes, I do have some advice for you. At 54, you are a bit older than most of us here – but I believe what I can tell you is universal and relevant. First of all – let’s look at the basics. From a positive standpoint – you are in great shape and health, and you have zero debt. You also have a great attitude – and you want to get back on the horse. Those all provide an excellent foundation for you right now … which means you are better off than a lot of guys in your situation.

Now let’s look at the issues. You are currently attracting overweight women or women in their 60s. Since you are 54, this represents your “low hanging fruit” … your own personal “base level” which you state you are not interested in. I submit that at least you are attracting SOMEONE … and you now just have to work on attracting the type of woman you really want.

My suggestions boil down to these bullet items:

1) Revisit your overall appearance … the clothes you wear, your hygiene, your teeth, how you carry yourself (what you exude). Have a female friend help you out here, if possible.

2) Do an attitude sanity check – spread good karma, avoid insecurities, be a good listener, learn to recognize and avoid ruts.

3) Create a dating strategy for yourself to meet the type of women you want to date

4) Periodically revisit and refine what you come up with for items 1), 2), and 3) above.

Going into detail on the above is too much for this Q&A, but I discuss all of it at length in the Midlife Dating Advice section. Here are the URLs to the subsections that I suggest you read through. The first two links come from the Midlife Bachelor Personal Makeover section.

Personal Appearance Rev 2.0 – Look the Part
Attitude Adjustment / Mental Makeover Rev 2.0
Develop a Strategy for Midlife Bachelor Success

Here are a few high-level elaborations for you. On the personal appearance front, you need to make sure that you are dressing yourself with your target female market in mind. And if your teeth are yellow or jacked up – I’d attach a high priority to getting those fixed. There’s not much you can do about baldness in the short-term … so I’d say just go with it … you could even shave your head. If you have any other outlying conditions – like spider veins on your face, get those lasered. Get rid of any hair growing out of your nose or ears … trim those Andy Rooney-style eye brows. You get the idea. Again – a good female friend can coach you through a lot of this.

On the strategy side, read the section of this site I highlight above. The basic idea is that you want to first identify the type (and age) of woman you want to go after … and then you’ll need to proactively do things to get yourself in front of that type. If you are doing the internet dating thing, you should carefully reconsider the photos you post of yourself … along with what you write in your profile. A good female friend can be a big help with all of this.

Now if none of the above works, you could buy yourself a Corvette. ha ha My neighbor, Chuck, did that – and now he drives around with younger women in his car. [He’s 54, too.] A former neighbor of mine named Gil who was actually age 70 took a different path … he started hanging out at strip clubs, and passing out $100 bills … and he wound up dating a 21-year old bombshell Latina stripper who let him take cell phone photos of her nude. (See Wakeup and Smell the Coffee in Your Midlife Crisis for that story). All I’m saying here is that there is a fairly wide range of strategies available for you to experiment with!

Good luck – let us know how things go. Don’t forget to check out our Midlife Forum – there are both men and women there, so you can get a range of opinions on specific topics or questions.

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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.