What Happens When You Date Someone Under 25

I get a lot of emails asking how young is too young to date. And, not surprisingly, most of these emails come from men. Ok, all of these emails come from men. So as a way of answering these “gentlemen,” here’s what happened when, for the first time, I went out with a girl under 25.

Hey baby, you come here often?

Normally, I don’t date young women. I’m 32 (as far as you know), and anyone under 28 usually feels a little…undercooked to me. But a friend of mine, who is, let’s say, a douchebag, recently made an impassioned case. “Younger women are more fun,” he douched, “they’re better looking, and they haven’t been messed up by bad experiences with other guys yet.” He liked to do the messing up himself, you see. This was a gentleman who only after great argument could I get to raise his desired age range from 18-22 to 18-25 on Match. And he’s 35. Did I mention he’s a douchebag? For some reason though, from this person who one should never take advice, I took advice. And of course, because it’s this site, I regretted it deeply.

The girl I chose for my youth experiment was 23. Actually, the one I first chose was 24, but she stood me up – the only time that’s happened in the 100+ Internet dates I’ve attended. A person who is wise would probably have taken that as a sign, but such a person would probably not detail each one of their dating failures on the Internet for others to read, so why even go down that road? 23, however, did show, and she was surprisingly delightful.

She was quiet, to be sure, but had some zip on her fastball once I coaxed her out of her shell. She was a journalism student and from my hometown (as far as you know) of Boston, so my interest was piqued. And, yes, alright, I’ll admit that she was quite attractive. But in that 23 year-old, gravity doesn’t exist, I never have to go to the gym so I really haven’t earned looking the way I do sort of way. So there’s only so much credit you can give for that. But it was a nice and very mature first date, and much to my surprise, I asked her for a second. Say it with me now…big mistake.

I believe she walked right through the middle of this…

I don’t know when people learn to carry umbrellas or buy umbrellas or well, own coats, but apparently it is 24 years and up. It was raining the night of my second date with 23, and she was soaked. But not in the normal way that people get soaked when they’re caught in the rain on the way from the subway or when waiting for a cab – she was SOAKED. Like she had drowned but forgotten to pass away. Dripping, sopping, preposterously wet, from head to toe. I asked her what happened and she looked at me like a crazy person. Obviously further explanation was needed. “You’re so wet,” I said. “Oh, yeah, I had to walk.” That’s all she said. “I had to walk.” Like it was a sentence for a crime she’d committed.  She had walked twenty blocks in the pouring rain and not stopped to get a $3 umbrella or a $6 taxi at any point. Now she was going to sit down with me for dinner in clothes that were more water than fabric and try to have a pleasant evening? It was ridiculous. Her clothes were sticking to her. There were puddles under her shoes. It was the sort of thing a 5 year-old would do. They’d laugh and dance and play in the rain, then when you explained to them that they’d now have to be wet for the rest of the evening, they’d look at you confused and forsaken. The polite sushi ladies were apoplectic, and as usual I was right there with them. (Polite sushi ladies and I agree on most things.) I was growing concerned with my plan to master the under-28s…

We talked for a bit, but 23 was, understandably, quite fidgety. The quietness I noted during our first date seem to expand when wet, and complete sentences were getting hard to come by. The night was officially entering the awkward zone, and for the fifty or sixtieth time in my life I was cursing My Friend The Douchebag. Then a strange thing happened. Or rather, a stranger thing. She just…stopped talking. I asked 23 what her plans were after she graduated (did I forget to mention that she was still finishing up college? I don’t know how I could’ve forgotten that…), and she didn’t respond. Not immediately, or anytime close thereafter. It had to have been at least a minute of silence. Not really sure what to do, I decided to just ask the question again and see what happened. Again, no response. There didn’t seem to be anything else to do but wait.

The only thing the night was missing…

The night took on sort of a bizarre subtext from that point. Basically, it was a game show. I would say something, then she would wait as long as humanly possible to respond. Unwilling to bend to the pressure, I would wait longer still to fill the empty air with a follow-up remark. It was as if whoever could stand the awkwardness the longest would receive a wonderful showcase of prizes and vacations to exotic lands. Really though all either of was going to win was a confused trip home. Alone. But it didn’t stop us from giving it our all. I would open my mouth, about to say something, then close it and turn away. She would lean in, look like she was going to explain exactly what had gone wrong, then grab an California roll and pop it in her mouth. It was breathtaking really, and a performance that far exceeded her age.  If I had any idea what was going on, I probably would’ve swooned with delight.

The evening ended anti-climatically with 23, as she gave me a damp half-hug goodbye and scuttled off into the night. I never figured out exactly what I did to upset or aggressively disinterest her, but I imagine it was my fault. I have that sort of way with women. I did learn one thing beyond all measure however: do not, under any circumstances, listen to the douchebags. Date who you want to date, and if you’re 32 then 23 is most definitely way too young.

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8 Responses to What Happens When You Date Someone Under 25

  1. kmparis says:

    Man, there was something seriously wrong with that girl. I’m 23 and I know how to use an umbrella and I can afford a taxi, and in defense of young women everywhere– there are bad ones and there are good ones, and you seem to have found one with some sort of severe social anxiety. I doubt she’ll be much better in ten years, and it’s probably better for her to stick to dating people she knows in real life first. Jeez, this story was just kind of sad.

  2. kmparis says:

    In defense of young women everywhere, there are plenty who don’t know themselves yet and plenty who do. I’m 23 but for God’s sake, I know to use an umbrella when it’s raining. You seem to have found someone with some severe social anxiety, and the whole post was just kind of sad to me. She sounds like she should stick to dating people she knows in real life. It can be extremely intimidating to go out with men who are upwards of ten years older than you; sounds like she wasn’t really a match for the pressure.

  3. Chris says:

    1/2 your age + 7 is the lowest you go. you were right on the edge my friend, playing in dangerous territory. that was your problem.

    After reading your story, maybe she wanted you to off her a way to get fresh clothes? Not really sure, very odd behavior. I mean I date 23 year olds (I’m 25) and have never encountered something quite like that.

  4. D. says:

    Yeah…I had a somewhat similar experience when I was 32 and the girl in question was very recently 24. Without going into specifics, the thing that made me walk away from it was that she reacted to a particular situation in a way that just struck me as…well, really juvenile, actually. It was probably age-appropriate for someone who was 23/24 or if not age-appropriate, at least sort of less surprising, but it just threw me. I had a “Really? Aren’t we beyond all this crap?” reaction until it hit me that, no, she WASN’T beyond it, and really had no business being beyond it yet.

    It wasn’t that she was immature. She was plenty mature for her age. Key phrase: FOR HER AGE. Her level of experience simply didn’t match mine, and that wasn’t a criticism of her. I’d just been on the planet longer than her, but that gave me more experience and, therefore, more perspective.

    Once in a while, I suppose it can work, but it definitely doesn’t work for me. I’ve also learned it doesn’t work for doing something “strictly casual” either. A 23-year-old might suggest “I’m totally cool with that” up front, but that won’t last (in my experience, anyway). By contrast, my experience with older women (say, 40-somethings) has been that they totally get when things are strictly casual and with all but a few exceptions, generally mean it when they say “Works for me!”

    Again, that’s not a dig against younger women or 23-year-olds specifically. It’s once again a factor of experience and knowing yourself and your own limitations. I suppose folks have to go through the “I’m cool with it……..wait, no I’m not” experience before they learn that sort of thing doesn’t work for them.

  5. gillian says:

    TO reply to the guy who was googled before his MEETING can’t say it was a date because he told her he was staying an hour because he had a party Nothing wrong with someone googling you and it shows she is honest telling him. To be honest it is a bit insensitive to tell someone you just met your going to a party. Maybe this is a case of men are from mars and women from venus because i can totally understand the woman Also the fact you commented on her job and being rich shows you in your true light MR

    • APB says:

      Gillian, I know “women gonna’ women”, but that whole post flew over your head. Are you the woman in question, by chance?

      It’s even worse to assume someone wants to spend FIVE FREAKING HOURS with someone else on a “coffee date”!

  6. Rick says:

    This article made me laugh, your date sounds eerily familar to one I had a couple of years ago. I was 33 and she was 23, I picked her up at her Metro stop in D.C. and went out to an early dinner. She acted as if I wasn’t there, talking to herself, not answering any of my questions and then wanted to go shopping while I tagged along; she seemed to have A.D.D. or something. The night ended up at her place where she stripped her clothes off in front of me, offered me a drink and then promptly went to bed (locking her door) while I hung out in her livingroom finishing my Vodka. I figured maybe she was nervous or was playing some new aged “hard to get” game and I wasn’t privy to the rules.

    I figured things would be more familiar in a follow-up date so I called her and we set something up. The second date was worse and I couldn’t wait to get it over with; it was like being on a date with a 14 year old girl. She was completely different; a mouthy know-it-all and wouldn’t look me in the eye. I told her I was tired and cut the date short. I didn’t bother calling her back, but a couple of days later she called and wanted to know “Where we were going with this”. Really?

    She was within the 1/2 Your age Plus 7 rule too. I later dated two women aged 28 and one 29. Both 28 year olds seemed much more mature, but in the end they were nearly the same as the 23 y/o. At 35 right now, 4-5 years younger is all I can stomach.

  7. OldEnoughToKnowBetter says:

    Actually, it always has to do with the woman – remember there are 50 year olds that STILL can’t carry on a coherent conversation. One of the best relationships I have had started with flirty eyes in a restaurant where I was sitting with my kids (not as cute toddlers, but in the semi-brat stage of 9 and 12) and an incredible reconnection via Craigslist Missed Connections, which for the record I had thought to be populated by highly delusional freaks.

    After beating the odds at finding each other, I found that she was 24, and at the time I was 50. Yeah, I know – LITERALLY young enough to be my daughter, hell she could have HAD my daughter!. But for some reason the age difference didn’t matter as far as the attraction went, and she has continued to be one of my best friends after the relationship got derailed by the usual things that happen when you date someone who is headed to grad school halfway across the country.

    So yes, the rules apply; and no, they don’t.

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