I wrote this post in 2006, when I was a whipper-snapper of 39.
On the subject of men and aging, a friend of mine told me a wonderful story yesterday. With his permission, I repeat it. My buddy "Sean" is 39, just as I am, and single. He goes to a Starbucks a few miles from here almost every day, and in recent weeks had been smitten with a very attractive, outgoing young barista there. She’s a Citrus College student and is about 19. For his (our) age, Sean is a handsome fellow; we originally met at the gym.
In any event, Sean and his young barista had been getting friendlier and friendlier, and Sean had been thinking of asking her out. (He didn’t tell me this beforehand, knowing my strong feelings about older men/younger women relationships.) In any event, on Tuesday afternoon, the pretty barista asked Sean a question after taking his order.
Barista: "Uh, can I ask you a personal question?" (Sean told me he was "stoked" when he heard this, thinking she might be getting ready to make the first move.)
Sean: "Sure."
Barista: "Are you single?"
Sean (now sure the gal is interested, and getting very excited): "Yes, sure am!"
Barista: "Well, I know this is weird, but you seem really great and I really want to introduce you to my mother. She’s really awesome, and I think you two would be perfect together."
Sean confessed this to me, and was more rueful and chagrined than devastated. I gave him a very hard time, of course, laced with compassion and humor. Until Tuesday, it hadn’t been driven home to him how younger women (mostly) see guys our age. But he’s starting to get that we are not as we were, and that’s not only not a bad thing, it’s pretty awesome. Sean says the barista gave him her mother’s number, and he’s considering calling. (She’s prepared her mom for the possible call.) I hope he does at least give it a chance, and I’m hoping that this little episode has ended his fantasy of eternal youth once and for all!
In any event, I’ve heard similar stories before (why do I think this scenario was in some sitcom, once?), but never from someone so close to me. And since like many 39 year-olds I’ve been ruminating a lot on getting older lately (and writing a lot about age-disparate relationships), this anecdote came along at just the right time.






1. Stay grateful and remember where you came from.
2. Keep striving.
3. Don’t get obsessive about it and realize that it’s quality not quantity…..that you already do and have done plenty…..and that you are more of service by doing good work for fewer than by doing okay work for many.
This has been a Bill” I can manage others’ lives better than my own” Funt presentation.
That reply was meant for today’s new post below this one.
Hugo,
as I have by now often repeated here, I’m a bit of a very late bloomer when it comes to success with women – so it’s a bit hard for me to speculate how women would have reacted to me in my early 20s had I been as – for the lack of a better description – sexually confident. I’m not thirty nine, but a bit closer to 39 than to 19. I always thought that younger women would never be interested in guys about ten years older – but they are, and more of them seem to be than not.
Maybe that’s a matter of male confidence being more tied to social accomplishment and female confidence being more tied to appearance makes such an attraction pattern more likely than others, I really don’t know. And in my case, I can’t really compare – and my first “girlfriend” was older than I was. But I do think that both younger women and older men think of each other – if nothing more – as a particular form of ego validation and status affirmation.
I think that there’s a world of difference between the way in which a 19 year-old woman thinks of the flirtatious attention of a man twenty years her senior and the way in which that man interprets her flirtatious attention.
If you’re a freshman girl in high school and a hot senior guy flirts with you, that’s status affirmation. If you’re a college frosh and a middle-aged man flirts with you, that’s tiresome and so frequent as to be anything but flattering.
Hugo,
“If you’re a college frosh and a middle-aged man flirts with you, that’s tiresome and so frequent as to be anything but flattering.”
Frosh is Freshman?
Thing is, that’s what I used to believe. By now, I’m not so sure anymore… of course women getting will be as annoyed by unwanted attention as they will appreciate wanted attention. But I doubt that age is a decisive factor in determining unwantedness – to a degree of course. Sean Connery will be too old by now even for most female fans of James Bond. But ask a 19yo about George Clooney…
I my personal – obviously limited and recent (spanning about 3 years now) – experience, I’d say that women generally seem to be more attracted to men who are (a bit?) older than they are. I remember talking to one now 22yo who seemed interested in me, and I mentioned my age in a way that was designed to tell her that I thought I was too old for her and that she was too young for me… her reply… “I look around, I only see boys, I see you, 10 years? Perfect age difference.”
And this is just the story most to the point. A lot of others point in the same direction. I don’t know. Maybe it’s really just me, and I’m not able to separate attraction to me from attraction to more mature men. But this is definitely my experience.
You can’t pigeonhole women and their desires. What might be “tiresome” for one woman may be refreshing for another. All women have a slightly different idea of what they consider attractive. Same thing with men.
Some young women are into much older men but most aren’t. Hugo’s point still stands. Especially if the age difference is more than 10 years and/or that woman is over maybe 35 or 40. Basically, women start to become less interested in older men when older men start to look “old”.
I come from a line of men who married women older than themselves–my grandfather was 11 years younger than my grandmother, my dad was 3 years younger than my mother, my brother married a woman a few years older than him, all my serious girlfriends were older than me–but then I got involved with a lady 2 years younger than me, just a kid really, and we ended up getting married. Funny how life works out.
Anyway, did the guy end up going out with the barista’s mom? Was she a clever, funny and attractive woman, with the wisdom that only experience can bring, a true companion for a man matching her mature years? Not to mention a woman who’s been around the block a few times in various company, who knows how to enjoy herself in bed, and help a man enjoy himself too.
Older people belong together; forget these young girls who haven’t lived yet. Let them grow up with the guys their own age and be happy.
Sean did go out with the barista’s mom. Mutual lack of interest apparently.
Ah. Well, you can’t force these things.
But we have to accept the possibility that Sean really is attracted to cute babes, and not to women his own age. If that’s true, I’d call it a problem for Sean, and for both the younger and older women.
I get this. I check my sense of agelessness though and, in any case amd in a wonderful relationship and am not looking for a woman, of any age. I still harmlessly flatter myself though that much younger women who make eye contact and smile are attracted to me.
Truth is they likely see a not-bad-looking 40-something man with a sparkle in his eyes (put there by his loving spouse) and respond without the reserve they would exercise with a potential mate.
Frankly — I really prefer a little harmless self-flattery to that rather neutred reflection of myself. In any case, as I said, it is all hypothetical since I am not wanting.
I notice much younger men making eye contact with me sometimes (I’m forty), and I too sometimes flatter myself that they find me attractive: maybe they do; maybe we’re deluded! I did notie one of my 19 year old students quite obviously eyeing me up, but hat possible had more to do with him being bored – he does also tend to fall asleep. But I can also remember just switching off and feeling creeped out by proper flirting from much older men (more than 10 or 15 years – so their 35 or over to my 20) as a young woman. They seemed to flirt in a different way to the men/boys my own age did, much more knowingly, and as if they had some agenda I sensed I wasn’t keen on or that I coudn’t connect with. Boys my own age seemed more gentle and equal about it, things seemed develop as a result of us sharing experiences. I still feel that way, that attraction which is based on connection, shared experience and being on a level is the best kind for me.
I too sometimes flatter myself that they find me attractive: maybe they do; maybe we’re deluded!
Or maybe you just think I’m 19; I look awfully young for my age and have been quoted as anywhere from 4-7 years younger than I really am; I’m not 30 yet but I’m pretty close. The most embarassing time is when a friend of mine though I was still in high school.
This presents as a bit of a dilemma because I’m not interested in dating much younger women (last time I did that was when I was 23 and she was 19; I didn’t like it.); my social circle, up until I graduated college, was 2-3 years older. I do feel sometimes I’m not taken seriously when I try.
“Sean Connery will be too old by now even for most female fans of James Bond. But ask a 19yo about George Clooney…”
The thing is, 99,9% of men are not George Clooney. Or Johnny Depp. Or Clive Owen. An overwhelming majority of men who go after women half their age are not incredibly handsome AND internationally famous AND talented AND charming AND rich etc. And just because a 19 year old woman swoons over George Clooney doesn’t mean she wants to date the 40 year old average Joe. Just like a 20 year old man who has a strict “no older women” policy would probably make an exception for Salma Hayek or Angelina Jolie.
Being attracted to (older) public figures doesn’t really count since they are almost always much more attractive and often much younger looking than the average person, not to mention all of the other added benefits I mentioned before (fame, charm, wealth etc).