Midlife Crisis of Confidence

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DEAR MIDLIFE BACHELOR: I am 43, and a few years ago, I lost my job and moved in with my dad. I started working out at a local gym, and I got along with a lot of the college-aged men there. In turn, the college-aged girls became friendly with me, too. I never asked any of these girls out because I thought they were off limits. It was only when some of them started asking me out that I became uncomfortable. At first and because I was down on my luck, I thought they were teasing an old guy but then I realized all these people thought I was their age group. So, it wasn’t that I was just an interesting older guy, it was as if I was a recent college grad. None of them ever even asks how old I am. I haven’t changed much in terms of looks since I was in college. Even older people think I am in my 20s. Some of it is because I have a very easy-going, fun-loving attitude. All my friends in their 40s have steady jobs or are married, and so I have no choice but to hang out with the younger people. So what’s the problem?

Recently, I have started going out in groups with some of these 20s people. Obviously, I have fun but I fear they will discover my actual age. It was an accident that we all saw a movie and got some dinner and now they all want to keep getting together. Additionally, embarrassing things happen like getting fixed up with a 19 year old which is flattering but terrifying. There’s a 23 year old girl formerly from my gym who won’t stop calling me or emailing me. She actually called me a wimp for not asking her out! At this point, I have been avoiding her but it won’t last. I don’t want to get a rep for being ghey. These college guys in the area are impressed that I can talk to women so easily which is astounding considering how careful and shy I am. Usually what happens is that I hold the door open for one or let them use a workout machine before me. Apparently, this type of behavior is so rare that it makes me a stand out.

Most of my friends my age don’t believe me when I tell them I have this issue and I merely wonder out loud am I complaining about a good thing or am I right to live in the shadows? I don’t make a lot of money right now so it is very tempting to date 20 year old women who don’t expect a lot. They have nothing to fear from me because even though I sound like a failure, I am a very responsible person, have no bitterness and I always enjoyed making women laugh and feel special. It’s like a domino effect women see other women hugging me or talking to me and suddenly, like electricity, women I don’t know start smiling or talking to me. And yet, I never ask any of them out. I find ways to disappear; stop going to this store, stop having coffee at that cafe, change my workout schedule.

I am very lonely right now. I haven’t had a girlfriend for almost 3 years – partially because I am in this rock/hard place. If I ask out someone in their 30s, they consistently put pressure on me for commitments which I feel uncomfortable with, or they look down on me because I have no career. I haven’t been able to land a permanent job in 5 years after almost 2000 applications. The younger women are more accepting but I have only gone out with a 21 yr old once because she cornered me in a coffee shop and demanded I take her number. That didn’t work out primarily because I couldn’t stand dealing with her punk rock friends. Is there any problem with dating a woman more than 20 years younger besides your own personal anxieties? It would be nice to just date until I could get my life back but it makes me wonder about myself that I can identify so much with people half my age. I don’t know if this is something you have heard of before. Arthur, age 43

MLB RESPONSE: My initial reaction is that you have great/obvious potential to date some of these outstanding much-younger women – and the only thing holding you back is your feelings of being down-on-your-luck career-wise. You have to keep in mind that in these times, MANY people are unemployed … some for extended periods of time. This is nothing to be ashamed of – it just is what it is.

One of my very good friends (Cornfed Ed from Iowa) went through something similar to what you are going through. He lost his job, lost his home, his wife divorced him … this was several years back. He had no money whatsoever, but he looked younger than his age 40 … and he had a pretty good attitude, and was smooth with the ladies. He would just tell these women flat out that he was unemployed, and that he couldn’t afford to take them to dinner (because he also had a young son that he had custody of). And the bulk of these women were understanding – and the women paid for their dates. So he practiced “full disclosure”, and became a dating maniac. He even started attending a local junior college during his period of unemployment – and met/dated a handful of 19/20 year old women. I was in awe!

I also work out a gym, and enjoy the company of the young early 20s perky women there. [I live with my girlfriend so I don’t ask any of them out.] But they will do things like exercise with me … and I am so entertained … and I tell them so. I don’t know if any of them would date me if I were single, but you obviously have that option – so you should definitely go for it. [Remember – the midlife bachelor motto is ALWAYS GO FOR IT. If there is any doubt about what you should do in any given dating situation, just refer back to that rule. ha ha] You must also keep in mind that some younger women (for whatever reason) want to date older men … so my suggestion is that you use what you’ve got, and see where it takes you. Also remember that “practice makes perfect” – which means if you do go out with one of these young hotties, and if it turns to shit – then don’t let that ruin your momentum. Just learn your lessons, and continue moving forward. Read the section here on this site called Periodic Re-Evaluation of your Midlife Bachelor Strategy for an elaboration … under the section called Develop a Strategy for Midlife Bachelor Success. Sounds like you have a pretty good strategy already though – the “nice friendly guy at the gym thing” appears to be working quite well for you!

My other recommendation to you is to keep looking for a job … maybe develop a Plan B if Plan A is not working out for you in terms of a career … and try to keep a positive mental attitude. Everything happens for a reason – and fate has brought you to where you are right now. It is up to you to make fate work for you with respect to dating, and also with respect to your next career. The only real issue you have right now is in your head – it is a crisis of confidence, and you can work through that. You might check out the section here called Reaching Midlife Bachelor Personal Equilibrium … under Midlife Dating Advice. Good luck – please report back with some good stories about dating young twenty-something hotties! Wooohooo!

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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.