How to enter the dating scene gracefully, in your twenties.

March 18, 2012 8:50 PM

In my mid-20s. Am just now really getting into the dating scene. Help me figure out how not to deal with this like a teenager.

Hi. I’m a 26-year-old woman. Until late last year, I was a virgin. I’d been putting my energy into school and my career and was dealing with a lot of anxiety issues around men. Though I did go on the occasional date, I really didn’t know what to do with male attention. Now I’m just starting to catch up.

Also, I’ve only had two real ‘relationships’ to speak of: one when I was nineteen, and one until about a month ago. The longest relationship I’ve ever had was about 3.5 months plus a month of long distance; my average is about 3 months. In both instances, and, in fact, in every dating scenario I’ve even entered into, I was the person who ended it. In the first case (what turned into a LDR) it made sense for things to end because we were probably never going to see each other again and were both quite young, going back to school, etc. In the second instance (my recent relationship) I really, really cared for him but he was unable to show me the affection I needed in order to feel valued (in fact, he had difficulty with affection in general) – plus, he decided to move to another city thousands of miles away.

But I feel like I need a bit of advice on how to navigate the dating world, being an older-than-usual rookie. I don’t want 3 months to be my batting average. I don’t always want to be the one who ends things. Already, I’m having doubts about whether I’m just not good at…well, working things out. Like I fly when the first bad thing happens, instead of dealing with wrinkles like an adult. (FWIW, the man I recently broke up with, who’s in his early 30s, has also never had longer than a 3 month relationship and shares my fears, which at first felt like something we had in common and something we could learn from together, and ended up probably messing things up for both of us). How can I make dating, and relationships, feel more natural, or make better choices at the beginning rather than going for guys who probably won’t be able to meet my needs? For men in my dating range (mid-20s to mid-30s), would knowing the lady you’re dating had never had longer than a 3 month relationship effect your opinion of her, or the way you approached her? In every other respect I’m quite mature, which makes things even more awkward. I’m not attracted to younger men; typically, I’m attracted to men who are at least in their 30s, if not older.

Any and all advice appreciated.

posted by anonymous to human relations (9 answers total)

Already, I’m having doubts about whether I’m just not good at…well, working things out. Like I fly when the first bad thing happens, instead of dealing with wrinkles like an adult.

Sometimes, the "adult" thing to do IS to "fly" when dealbreakers come up. You said you broke up with the last fellow because he couldn't show you affection and he was moving thousands of miles away. *Either* of those things would be a pretty firm dealbreaker for most average people. Those aren't just some silly little things. You did just fine there with the choice you made. Hey, you did really well in fact. I think you might be better at this stuff than you give yourself credit for.
posted by cairdeas at 8:55 PM on March 18, 2012 [4 favorites]

And --

How can I make dating, and relationships, feel more natural, or make better choices at the beginning rather than going for guys who probably won’t be able to meet my needs?

Can you make friends with them and get to know them a bit before getting involved romantically? That would give you a bit of time to find out what they're really like as people, what their issues are, etc., without pressure.
posted by cairdeas at 8:59 PM on March 18, 2012 [1 favorite]

For men in my dating range (mid-20s to mid-30s), would knowing the lady you’re dating had never had longer than a 3 month relationship effect your opinion of her, or the way you approached her?

As a man in this range, no, it wouldn't, and if someone happens to have a problem with it, then it's their problem, not yours. As long as you're awesome and you think you're awesome, other people don't have the right to hold small stuff like that against you.
posted by un petit cadeau at 9:01 PM on March 18, 2012

You have no idea how much better off you are having not habituated yourself into staying in relationships for their own sake.

Also: you will have no difficulty finding older men, so no need to worry about that.

Practice practice practice. Get to know your OkCupid community. Most of your dates are going to suck; that's normal. Don't worry about finding the right guy immediately -- right now you just need to figure out what kind of person you can function with. You're in no hurry.
posted by modernserf at 9:02 PM on March 18, 2012 [6 favorites]

he was unable to show me the affection I needed in order to feel valued

Judging by the amount of askme's about breaking up on here, it seems like a lot of people are not brave enough to break up with someone for the above reason. So it seems to me like you have a good head on your shoulders and are confident enough to go after what you want, and not allow yourself to be treated like shit. I say keep up the good work.
posted by costanza at 9:27 PM on March 18, 2012 [2 favorites]

For men in my dating range (mid-20s to mid-30s), would knowing the lady you’re dating had never had longer than a 3 month relationship effect your opinion of her, or the way you approached her?

Yes it would, without the detail that there were five years not in the dating scene and not in a relationship. Without that detail I would assume 7+ years of less-than-3-month relationships, which suggests not serious-relationship material, maybe some other kind of relationship instead.

But with that detail, not a lot, though I'd still be a bit wary for another reason - I'm of the opinion that everyone unintentionally fucks up their first major relationship, and in the clarity that only comes of surveying the smoking wreckage and the struggle healing a shattered heart, learns how to be awesome at relationships and awesome at life. (Or becomes bitter and twisted and hardened. Hopefully the former!)

You haven't done that yet, and I'd prefer you not do that with me. But if I like you, I like you, and I take my chances before someone else snatches you up! :-)
posted by -harlequin- at 11:13 PM on March 18, 2012

Costanza is right on; the fact that you were able to acknowledge the someone wasn't meeting your needs and end things means you have some natural talent at this dating thing!

I'm 25 and have had two relationships - one that was eight months to start, then on and off for a few years; the other for just two months. I just celebrated three months with my current boyfriend, and it's the first time I've been in what feels like a very healthy, adult relationship. I've been on OKCupid since I was 21 and have gone on countless terrible dates, which helped me a) realize what I am and am not looking for and b) practice my flirting, my catching red flags, etc.

As far as not choosing guys from the start who won't be able to meet your needs.. that's a lot tougher. In addition to my relationship, I've had a few other non-committed things with men, and this is the first guy that I actually chose who has been able to meet my needs in the slightest, really. Sometimes a man will demonstrate to you that he can meet your needs and then he can't. Sometimes he will think that he can and he can't. I dated a man who had issues with sharing his living space, and after about a month he told me to bring my stuff over to his place and spend the night. Within a few weeks he was asking if he could drive me home after we slept together and wouldn't even let me stay in his bed (at one point instead of bringing this up to me he went and slept on the couch!).

But you'll get better at identifying that kind of thing with more practice.
posted by anotheraccount at 5:19 AM on March 19, 2012 [1 favorite]

Carry on, keep doing what you're doing, check back in 9-12 months.

You seem to be keeping ahead of at least one major pitfalls ("you're not doing it for me. take a hike"), but there's not really enough information for us (or maybe you) to really notice a pattern.

When I was dating again (at 26, after 8 years of serious relationships), I went through focused/analytic phases and very casual phases, and both served me well.

Be yourself, and your track record shouldn't be an issue.
posted by itesser at 4:45 PM on March 19, 2012

"I don’t want 3 months to be my batting average."

I wouldn't worry about this because it doesn't mean anything.

You sound really cool and not prepared to settle and let it shake you.

Rock on sister!
posted by misspony at 2:46 PM on March 20, 2012