Dating Older Men: How Old is Too Old?

9 years ago

When my roommate and I go to a bar, we largely attract the attention of older men rather than males closer to our own age. (By “older,” what I mean is “noticeably older than myself.” Like 15 years or more.) I’m not saying these older men act like they want to “hook up” with us – most of the time they’re just looking for a conversation. (Or at least that’s the way they make it seem...I’ve never had an older man ask for my number.) There have been a few older men who were more overtly obvious about their intentions – I’ve had several blatantly walk up to me and say, “I think you’re beautiful” – but in those instances they’ve always said their piece and continued on their way.

(Continuing on their way is a good move, because otherwise my response would be, “Thank you. Now move along.” It’s not that I’m trying to be rude. I just don’t think “You’re beautiful” is a good opening line, no matter the person’s age – even if they’re thinking it; even if they really believe it to be true.)


Credit: Robert S. Donovan on Flickr

It’s not like we don’t catch younger guys looking at us – but they look from where they’re sitting, or standing. And I don’t have a problem talking to older men if they’re being nice, but I don’t see them as someone I’d want to go out with.

A good friend of mine, a woman in her mid-40s, has given me her opinion multiple times on the types of men she thinks I should be dating. “We live in DC,” she says. “You should be attending parties at embassies and meeting diplomats. Or you could be an executive’s wife.” My friend has good intentions, but all I say in response to her suggestions is, “I have no desire to go to a party at an embassy. I wouldn’t have any idea what to say to those people. On top of all that, I’m not looking for someone with a specific title – the man himself comes first.”

So how old is “too old” for me? I’d say ten years would be my max. But having said that, I know age differences of ten years or more don’t bother everyone. My older sister was married to a man eleven years her senior (they’ve since divorced), and my younger sister is currently living with a man ten years older than she is. A good friend of mine was married to a man fifteen years her senior for over six years (they married when she was nineteen).

I wonder...why is it that younger guys aren't as comfortable approaching my roommate and I than the older guys? Are the older men not as worried about looking “cool?” Does the possibility of being rejected not bother them as much?

I also think this phenomenon might be related to where you live. City Girl DClives here in my area. She went out with a female friend one recent Saturday night, and had this experience:

What I love about Marvin [a bar] is that it seems perfectly designed for meeting and conversation. You would think there would be lots of mingling. Instead, as we looked around, all we saw were completely sex-segregated groups. To our left were two women who could pass for models. Behind them, clearly gawking was a group of guys. Not once did the guys make a move. […] Pam and I were curious as to what the guys would say and decided to ask three attractive, well-dressed guys standing behind us. One was Indian, one Latin American, and the other second-generation African. We figured we would get a good mix of responses. Instead, they were pretty much the same guy. […]

They didn't feel the need to approach women and were of the belief that women should be more willing to approach them. Hmmm. I always find it suspect when a guy has decided that women should take the initiative in dating: asking out, paying on a first date, making the first move, etc. All I know is that these guys were typical of so many guys in DC. They seemed way too interested in saving face. Sorry, but being a guy involves some degree of regular rejection.

Tarahas the same experience with older men being the only ones bold enough to approach her, and wonders what’s up with younger guys.

Why is it that I find myself getting hit on by older gentlemen in Hoboken and not the younger fellows? Where are the bright young men of Hobo? […]

A girlfriend and I recently went to a bar in Hoboken on a Saturday night.

We were there to have a drink and watch her alma mater, the University of Virginia football game…hey, a great way to meet guys…young guys! WRONG! No one even approached us… The guys that were there didn’t even budge to come up and say hello. On the way out, I walked passed a young guy who hardly turned his head but did get the slight nerve and sober energy to say “bye ladies”. Ugh! And that, Ladies and Gentlemen, is a brief portrait of the wildly gifted charm imparted America’s Best – our Young and Upcoming World Financial Business Leaders of Tomorrow.

New blogger Jenny Prunaasks, “Does Love Have a Number?”

I am currently dating a man 10 years older than me. We met at my old job and ever since then we have been dating. Its been a year and a half and we are still in love; if not more than ever. It is not common to see someone dissaprove of us being together when they have not met my boyfriend. Just the age difference alone shows how wrong it is. The common arguments are… “He’s only seeking one thing from you and its not being with you.” “He is too old, you should be with someone your age.” and etc.

Problem is with that last argument is that every guy I meet at my age isn’t what I am looking for. I want to fall in love and be in that relationship. I no longer want to explore a bunch of bad relationships when I can have one great one full of love.

At the Huffington Post, Christine Hassleris asked for advice by a 27-year-old female dating a 42-year-old man. This is part of Christine’s response:

In my opinion, there is a lot more than just 15 years that separates you from your 42-year-old boyfriend. He's had a heck of a lot more life experience than you have. You are in your late twenties, a time in life when you are just beginning to become sure of who you are and what you want. You are creating your life while he is already in the prime of his. If you were 40 and he was 55, I would not be as concerned about the age difference as both of you would have had ample time to experience life and mold your identity. By dating someone so much older, you are missing out on being with someone who is in the same phase of life that you are; someone with whom you can share the joys and pitfalls of discovery.

The male perspective: Jay Rusovichis in his early 50s, and has this to say about attracting younger women:

Anyone whose reached middle-age has to face the fact that – no matter how we look or feel – we can’t outright cheat the clock. Let a few more years pass and we start to wonder whether or not it’s even appropriate to approach younger women. By ‘appropriate’ I’m thinking along the lines of …will she look at me like I’m out of my fucking mind for assuming she would consider me as a dating candidate? […]

Many young women simply don’t give a damn how many bootcamps you put yourself through every week. Or how interesting you think you are. Or how talented you are. Or how successful you have been. By this time, life was supposed to have yanked you out of the game and thrown you onto your Lazyboy, out in the suburbs, with a family, watching network television… […]

The truth is, a ever-growing number of young women are actively dating older men; particularly in big cities, because these tend to be more sophisticated than their fly-over sisters, and don’t hold the same appreciation for being treated like objects by young men. The same men who routinely take them for granted, and have nothing to talk about other than domestic beer. This notwithstanding, you still have to also accept the fact that there are a corresponding number of women who can’t fathom dating older guys from any perspective. They want Cinderella. They want Snow White. And intend to ignore the odds against realizing those fantasies in today’s world.

How old would be “too old” for you?

(Contributing editor Zandria also blogs at Keep Up With Me. She will continue to talk to older guys in bars as long as they don't start the conversation with, "I think you're beautiful.")

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