Dating at almost 60 is nothing like I thought it would be.

I actually didn’t think I’d really be actively dating at almost-60. I assumed I’d have settled into to a nice long-term relationship with a delightful man who was not my husband but offered many of the perks and none of the headaches of a husband.

So that didn’t happen and I was OK with that. I’ve always liked dating and never quite grasped the idea of finding a man at a tender young age and staying there for a lifetime. Serial relationships were more my style. We’d stay together for however long we could and, then, when it stopped working, we’d move on. There always seemed to be another interesting guy not too far away. And I (apparently foolishly) assumed it would always be that way.

But that was before I reached 55. Fifty-five must be a really scary number to men because I — seemingly overnight — went from a dating feast to a dating famine.

Part of the problem is the way I look. I look a lot younger than my chronological age and this throws men off. Dating is the only space I can think of that looking younger than your actual age can work against you.


Once I entered my 50s, it would work like this: A guy would flirt with me, we’d connect, go out a few times and then, at some point age would come up, either directly or as a reference point. And then, trouble.

Like the time we were discussing politics and presidential security, and I mentioned that I still remembered my mom’s reactions to the Kennedy assassination. Uh-oh. At first he thought I was joking. When he realized I wasn’t, he became quiet for a bit. The conversation eventually picked back up but it had lost some of its steam.

We went out once more and, over dinner, he “playfully” (at first) accused me of pulling a bait-and-switch on him — meaning pretending to be a lot younger than I actually was. Except there was no pretense. He assumed I was something that I wasn’t (a younger woman). I was about 10 years older than he was and he just couldn’t see himself with a 55-year-old.

And the guy I’d been dating for about six months. We were having a great time and age, somehow, never came up, although I now know he’s 2-3 years older than I am. One night, when we were out with my best friend and her husband, she asked what my plans were for my upcoming birthday and laughingly commented that she never thought we’d still be so happily celebrating our birthdays at this advanced age.

My date’s face froze. The other couple thought he was kidding but I knew he wasn’t. I could see it in his eyes. Two days later, he broke up with me, claiming he still wanted the option of having more children. (Update: It’s years later and he has not had another child. Whatever.)

So after a few more fiascos like that, I no longer wait for guys to “discover” my age. I tell them pretty quickly. Saves us both a lot of time, and saves me some hurt feelings since. Here’s what often happens:

✓ He likes me (or thinks he does).
✓ I, casually, work my age into the conversation.
✓ He retreats.
✓ On to the next one, for both of us.

And this is true if the guy is my age, younger than I am, or even older than I am.

I get it, kind off. Aging is scary to lots of people and we live in a culture that prizes youth above almost anything else. To most, a 58-year-old woman is just old.

Except I’m not. I’m awesome. In so many ways, I’m the best I’ve ever been. I’m more secure (financially and emotionally), can’t surprise anyone with an accidental pregnancy, have built a pretty nice life for myself, and won’t be issuing any “marry me or else” ultimatums. We can talk about it, but marriage isn’t a must-do for me.

While these men are still chasing youth, they may be missing out on a pretty spectacular woman. Not just me, but so many other women-of-a-certain-age whom I know to be pretty dynamic.

I want a relationship that is good and solid and fun and supportive and monogamous with a guy around my own age. Is that really asking for too much?



This post originally appeared on XOJane. Republished with permission.Click here for more Eleanore Wells on XOJane!

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  • Martin

    What a lot of you all aren’t grasping is your 55 is actually somewhere between 30 and 35 because you, unlike this woman, look your age or look older than your age. If you are overweight/out of shape, have kid(s) and/or no degree and career (aka broke) it’s closer to 30 than 35.

    It’s not fair but it’s a buyer’s market for a man with a degree, good job and/or good looks and physically fit until the day he dies. It’s a buyer’s market for young average to attractive black women from puberty until 30. Choose wisely. This is one of the failures of black feminism (ie waiting) that many don’t want to acknowledge. This women is being honest about the unrealistic fantasy that’s being sold to young black girls.

    • imnotasian

      now what?

  • jane

    there is someone for everyone truely this woman look real good for 60… but some women look like they are ready for a nursing home at that age …. men are about youth ,thats why so many of them pick wrong .. so many get trapped with babies they cant afford ,and in and out of dramatic relationships .. it all about some young chick who they think can put it down on them … and they can intro duce as my side peice …. rarely does a woman in her 20s or 30s really want to settle down ..some 30yer olds make the mistake of rushing to get a child to be left alone or single parent status which is worst than, than them haveing a woman a little older than him … dating someone 20 years older than you and your 40ish is nothing wrong cause if your 40 …do you need more kids by some woman seeking child support if it dont work out …. im over 40 and i feel like the lady in the article men are funny about age ,,i lie on my profile page and go back 10 years but that dont help me cause they dont want babies by some 30ish who havent had kids and want them …. people dont care who they have a child with as long as theirs a check…. i got lucky i ahave no kids …. i dont feel the need to have someone to care for my aging self …thats why i stay young in the mind ,cause children often cause people to act old …. lol …
    i bet you the lady in the article has either one child or non … she looks great … somewomen with kids look sooo old by 37 or 40ish …..
    me like a nice body ,pretty smile and a non chalant attitude .

  • Souflower

    Yo really just put my life story out there, it is refreshing to see it in print. Most blogs I have read are about 20-40 year olds, and I have moved so far beyond all of what they are concerned with. Like you I am financially, emotionally and physically LIGHT YEARS AWAY from where I was even 10 years ago.

    Too bad all of the men I have talked to in my age group (58+) are still looking for younger women. But hey, their loss, not mine.

    • Axona

      It’s so true. I am 58 old European woman who looks much younger than my age. My experience with dating is very similar to Xojane’s. Men my age are interested in casual relationship while still on lookout for women who are 10, or more years their junior.
      Younger man find an affair with an older woman exciting, but have no interest in serious relationship. Men who seem to be interested are typically two decades older than I am and look the part.
      Looks aside, there is usually a generational gap and common interest seem to be few and far in between.
      I would really like to find someone my age to share intimate moments, laughs and common interests, but to most men of my generation, my age seems to be a turn off no matter how accomplished, youthful and creative I may be in other people’s eyes. It makes me feel sad.

  • Deborah

    Men are so weird. And you are completely gorgeous! I dated in my 50s and didn’t get too much pushback. But men really are weird.

  • Jacob Hughes

    I suggest women over 50 fib just a little about their age to avoid being shut out and not given a chance. Later on if he likes you… he will overlook your typo. It worked for mom.