do second chances often convert to success?

August 10, 2007 5:46 AM

How to re-approach cute girl for something serious, with whom I had a drunken make-out session a couple of years ago?

Said Cutie and I made out a bit while out dancing one evening. We saw each other afterwards for a couple of "dates" but I rushed things a bit and it stalled. We haven't seen much of each other since, except when we run into each other every few months or so in our common office building.

There's obviously a physical attraction but I think she was put off by my drunken groping of her. Whenever I happen to see her I still think she is a great find, and tonight I convinced her on MSN chat to give me a second chance. I'm supposed to call her next week to arrange a date.


I am a great boyfriend when I'm with someone I care about, so how can I make Said Cutie mine? Ladies, tell me how I should romance her, excite her and win her over again -- without trying too hard.

posted by anonymous to Human Relations (8 answers total)

The answer to this question is basically always the same. Take it slow and get to know her. Don’t make it obvious that you’re trying to put the moves on her. Plan fun dates that combine some downtime (coffee, drinks, dinner, dessert, walk in the park) with some shared activity that will lead to discussion either during (mini-golf, hike, museum) or after (movie, concert). Try to suss out her “thing”—whether it’s chill conversation, food, or outdoor activities—and do some of those, while also introducing her to things that you like that you think she’d get a kick out of. Try not to get too physical too quickly (there’s nothing wrong with that, but if you want this to Last, that’s one way of communicating that you’re in no rush, that you expect to spend plenty of time with her). Compliment her respectfully from time to time.

And for goodness’ sake, no more conversations over IM except for in-between stuff. Call her to make plans. Nothing drives me crazier than a guy who’s too afraid (or too lazy) to pick up the phone. (I can see you said that you’ll call her next week, this is really just a PSA.)
posted by CiaoMela at 6:32 AM on August 10, 2007

Small tip:

If she asks, don't explain your motivations for seeing her again in terms of 'We made out once, like, two years ago, and I still haven't gotten you out of my mind even though at the time I scuttled our romantic chances.'

Stay casual for God's sake, it's a date with a chick from your building. Don't worry about being 'a great boyfriend,' just have a good time. That's the most positive thing you can bring to the hangout scene, man: having a good time and wanting/working to share it with someone. The more you think about Making Her Yours the more the manipulative character of early dating will shine through.

And as far as 'compliment her respectfully from time to time' goes, a less irritating (to me) translation might be, 'Notice when she does cool stuff, and let her know.' Emphasis on 'does' rather than 'has' or 'looks' or 'dresses' or whatever. You sure as hell don't owe her compliments, but if you're actually interested in her way of being-in-the-world, definitely let her know. (I hate the idea that you should ration out respectful compliments or anything else in order to 'succeed' at a relationship. If she's not worthy of your compliments, you're wasting your time; don't let yourself work too hard to find nice shit to say. The flip side goes for her, of course - she's doing you a nonnegligible favour going out with your ass on the basis of your !@#$ MSN conversation. Realize how silly the situation is and rise to its level of silliness.)
posted by waxbanks at 7:38 AM on August 10, 2007

Seconding the "slow it down". Dating was invented so you can get to know someone before you get involved with them.

Romance means different things to different women. But generally, no drunken groping, and listen more than you talk, ask her questions. And say her name frequently (we all love the sound of our own name). Also seconding the nixing the IM convos. I'd also avoid excessive texting just to say "Hey". Be a man and call her! Most guys don't, so that sets you apart right there. But trust me, she doesn't need, or want 10 calls a day (creepy).

I personally love it when a man gives me something that I mentioned in passing, or he does some random act of kindness for me. For example, preparing dinner one night, I was laboring chopping garlic and moaning that my ancient wood salad bowl recently broke. For my b'day, I received a new wood salad bowl, with a garlic press inside. It's cheesy to some, but I thought it was terribly romantic because it showed that he was paying attention and listening.

Good luck!
posted by socrateaser at 7:47 AM on August 10, 2007

Forget that you ever dated. Don't be overly familiar because you made-out at a party. After 2 years, you're different and so is she.

You need to build some trust. Go slowly. Pay attention to her, but let her set the pace. Given your history, she may worry that you're attracted to her because you think she's easy. You need to give her a chance to stop seeing you as a drunk groping guy and start seeing the guy who waited 2 years for a second chance.
posted by 26.2 at 8:02 AM on August 10, 2007

Show her that you have some self-control. Try not drinking alcohol on the next couple of dates and not putting the moves on her. Just be casual; that takes a lot of pressure off of you both.
posted by momzilla at 8:17 AM on August 10, 2007

I agree with momzilla -- in her shoes, given the history, I'd be watching like a hawk for any problems with drinking. Stay away from bars on this first date, and find things to do that demonstrate you have a lot of wonderful ways to spend time, and drunken groping is not your normal MO.
posted by Miko at 11:52 AM on August 10, 2007

Agreeing with most everyone here, but less that I--personally--would be worried about your drinking and more put off by a nagging suspicion that you only relate to women as "cuties" or pieces of ass. I'd add that what you do in pursuing this relationship should show that your interest is in her, as a person, not her, as a hottie. Yes, of course, tell her when she looks great--everyone likes to hear that s/he is attractive--, but waxbanks is dead on with "'Notice when she does cool stuff, and let her know.' Emphasis on 'does' rather than 'has' or 'looks' or 'dresses' or whatever", especially since it seems that you're basing this whole thing on physical attraction and drunken making out. This ask.me strikes me as though you are commodifying her (and yourself, for that matter) with the whole "she's a great find" and making her yours attitude.
posted by crush-onastick at 12:46 PM on August 10, 2007 [1 favorite]

I'm going to go slightly against the flow, there - the guy I ended up marrying, we didn't talk over the phone pretty much ever, and most of our pivotal convos occured over one form of IM or another. Lazy? No, we just both dislike the handicap imposed by less-than-full bandwidth conversation, coupled with lack of a backspace key.

So, if IM works for you, great. Do check if IM works for her, though.
posted by ysabet at 7:53 PM on August 11, 2007