I don’t think many of us, male or female saw it coming. Maybe if we did we would have managed our lives differently. In high school and college we boys struggled and strained to find girls who would give us the time of day. It was a girl’s world, not a boy’s at least not if you were gangly, awkward or otherwise unappealing, like I was. Nothing motivated me like finding a partner. Girlkind was my muse. Everything I learned about life I learned in the service of winning that elusive feminine heart.

I got good enough at it to win my wife’s affections. We were together for 16 years, breaking up at 40. I assumed my ex would tell all the women in the world that I was a loser and that I’d never get another date. But it turned out that there were lots of wonderful women as disenchanted with their husbands as mine was with me. The grief over my ex falling for other guys ended when other men’s exes fell for me.

There’s a window somewhere between say 35 and 55 in which a woman is very likely to be able find a second partner if she wants one. It takes a kind of focused dedication and commitment to the project, a faith that it can happen, not settling for compromise guys or casual encounters that waste the window. It’s hard to keep that kind of faith especially for women who either were burnt by prior partners—the many guys who cheat, lash out angrily, or lie, or just feel burnt whether they were burnt or not, women who with self-flattering certainty call their exes pathological narcissist jerks, even if they weren’t, even if what happened was mostly that the two had grown apart. It’s hard for a woman with a bitter taste in her mouth from past relationships to muster the faith to compromise with a new partner, using this window of opportunity to find a good new and lasting relationship. But many do.

Gradually the window closes down to a crack. Yes it’s still possible for a mid-fifties woman to find a long-term mates, especially if she’s lucky enough to age well and have the other attributes a guy would find exceptional. Of course, it happens but not nearly as often as there are women who want it to happen.

I’m 56 and dating again, women my age or thereabouts. Some own their circumstances realistically. They don’t think the world owes them anything. They’ve integrated their caution, are open to a long-term partnership but are soberly realistic about how things change over time, fewer available guys they’d want and would want them. They can imagine that it might not ever happen and have sufficiently satisfying back-up plans, loving the other projects that make life worth living or learning how to stand in love rather than fall, enjoying the company of those who come and go, loving the company of guys who fit in some ways but not in all the ways that would make monogamous commitment a likely success for either or both.

There are however lots of other women who seem much more unprepared for the circumstances they find themselves in, angry, resentful, feeling gipped and betrayed. They seem unaware of the change that happens by our mid-fifties or just unaware that they’re not exempt, thinking from it. They seem to insist on the fawning they got in their youth.

I understand. I think the world is fundamentally unfair and especially to women in an overwhelming number of ways. If I were one, I’d have a lot to be frustrated about including that no one seems to tell us that each gender gets a chance to be in higher demand and that it’s ladies first, leaving them far too often weaning themselves off of expectations of flattery that may have seemed easy to ignore or assume was a birthright, but actually becomes kind of addictive and is not a birthright the farther women get from their birth.

Like all people dealing with frustrated expectations, these women seem to move first toward moralizing about it, how the world and men should just show up and be what these women want them to be, both more attractive and more attracted. A recent spate of such dates got me thinking about how, when the tables were turned the other way, what it would sound like if a high school boy talked about high school girls the way these older angrier women talk about older men. Here’s what I came up with. Picture Justin, a high school junior:

Girls should be nicer. It’s really something how immature they are these days. They don’t know how to have a deep conversation about important things like video games. I try to get them to open up and be real with me but they’re just too shallow.

They’re so into looks. It’s crazy. I’m 5’7” but guys always tell me I look more like I’m 5’10. And I look good. Sure I’ve got a lot of pimples but they’ll go away. These girls ought to be able to see through them to the real me. But, it’s like all they think about is wanting some taller handsomer guy.

Lots of girls don’t even seem to want a relationship. They’re totally distracted by school or work or extracurricular activities. It’s not fair. It’s like they’re not going with the program. We should all be having our first experiences of true romantic love. I’m ready, but where are they? They’re just not showing up. I think some are just afraid of making a commitment. Anyway it’s pitiful and frustrating.

My heart is in the right place. I just want what every high school boy deserves–a kind, generous, compassionate, interesting, caring, sexy, fun girlfriend. I can’t believe how long I’ve looked but the girls at least around here, they’re too egotistical or narcissistic to be willing to even consider me.

When I get one to talk with me, afterwards she’s like, “yeah, talk to you later.” But then she doesn’t. I mean that’s just weird. That’s just playing games, and I’m not into games. They’re not being real and authentic. If they were real and authentic with me they’d show more care, compassion and interest.

Online I’ve met girls from farther away. They respond maybe to one or two IMs but then they don’t follow through. My dream is that we’ll talk and they’ll see how exceptional I am, and then they’ll find a way to visit me out here, and we’ll fall in love and commute the long distances to see each other because our love will be true. They’ll recognize that I’m uniquely kind, openhearted, spiritual and compassionate, a gem, a special one. There has to be a girl like that because I really, really want there to be, and because I can picture her. And I’m a realist. Not like other boys. I don’t make stuff up. I see how things work and I work with it.


I have faith. I’m committed to my dream that there’s one honorable girl somewhere who will see that I’m right and won’t be afraid of commitment. She’ll do the right and responsible thing, and fall in love with me and be my partner. I deserve that and she’ll know it. She won’t look at other guys. She’ll be faithful and true to my vision.

When my older sister was helping me with my homework last night we got talking about this stuff. She suggested that maybe I should think about other possibilities. Like what if I get all the way through high school and no girl is available? She’s all like, “What if she never shows up? Maybe you should think about how to be happy without it,”

I just said, “She’s got to show up.” My sister can be unbelievably discouraging. There’s a lot of boy haters out there, and I’m beginning to think my sister is one too.