Should I go for the kiss again?

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songoflutie asks:

I met this girl on Facebook and we used to study together and we kissed when we were teenagers (like, 7 years ago) and we started talking again. I invited her to a date and it went very well; our personalities fit each other, she laughed at all my jokes and her body language was pretty receptive. Then, at the end of the date when I tried to kiss her, she rejected me. I felt bummed out and tried to keep the funny stuff going but I think she noticed. She said she just got out of a relationship because her boyfriend cheated on her. I asked if she still had feelings for him and she didn’t say yes or no.

At the end of the date, she said she’s up to a second date; but I’m pretty confused if she wants anything other than friendship. When we date again, should I go for the kiss again if she’s still receptive?


Demetrius says:

Wait, hold up. Why do you think you should go on a date with her again? Before I even answer the whether or not you should kiss again question, we need to tackle that.

Maybe I’m missing something but, this girl is obviously still dealing with her feelings for her ex, right? I’m not missing anything here am I? Maybe it’s just me, but if someone tells me, through words or actions, that they aren’t ready to kiss me, or that they aren’t over their ex, I wouldn’t consider dating them. I’m not saying that I would burn a bridge and salt the earth as I move on or anything, but I wouldn’t be sitting here wondering if I should go for another kiss. Or another date, if we’re being honest.

Here’s what I’d do in your situation: First, I would reach out and say that I had a great time, but think maybe now isn’t the best time for us to date. I would express my willingness to be friends, but make it clear that as of right now, I don’t think dating would be a good idea but would be open to it when she’s ready and has moved on. I wouldn’t give her a lecture about how she’s clearly not over her ex or anything, I would just be clear that after the date I realized that maybe now isn’t the best time to pursue her. If she presses for a reason why, I would say that it seems like she’s not over her ex, and that dating right now wouldn’t be giving ether one of you a real chance at connecting, but I’d be open to reconnecting if she ever gets over her ex.

You might be thinking that I’m wrong, and that she just needs time, and that she can get over her ex while dating you and I would disagree. Which one of us is right? Neither, quite frankly. Remember I said “Here’s what I’d do”, well that’s because it’s how I date. If you’re an optimistic dater, you might date with your primary driver being hope. My primary driver in dating, and when I give advice, is practicality. Is it possible to woo someone who is still hung up on their ex in the hopes that they will be able to move on while dating you? Yes, it’s possible. Is that a probable outcome? No, it’s not a probable outcome. Would it be practical to do something that requires a lot of time and effort with minimal chance that you’ll get a return on all your effort? No, and that’s why I advise against it.

However, I can understand how having a hopeful approach to dating appeals to people, so if you want to go through with another date, go for it. My word isn’t law or objectively right, so if you’re comfortable using your valuable time and money on dating someone who is clearly not ready to date, go for it if you’d like. Maybe your persistence will win her over, you’ll end up together, and everything will be all sunshine and daisies and happily ever after and you’ll chuckle when you think of the terrible advice I gave you and I’ll hang my head in shame, in perpetuity, for being so wrong. If you do want to take her on another date, you should check to see if she wants to go on a date platonically or romantically. If she says that you can hang out as friends, don’t try for another kiss. If she wants to see you romantically, ask if it’s okay to kiss her at the end of the next date, since you were rebuffed before. Maybe she wont want to kiss you on date number 2, but maybe things will change if you make it to the third date. Who knows, right?

Anyway, you’ve got my advice on how I’d handle things, which is to stop pursuing her romantically. You also know how to approach pursuing her if you’re feeling optimistic. Whatever you decide, as always, I wish you the best of luck.

Good Luck Out There.

Demetrius Figueroa

Demetrius is a sex, dating, and relationship writer based in Brooklyn.

2 thoughts on “Should I go for the kiss again?

  • July 9, 2016 at 1:46 pm
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    I’d say everything is going well. A teenage kiss 7 years ago….well….doesn’t mean much, but clearly there seems to be mutual attraction and the ‘date’ went well.

    Either she gets over her ex or she doesn’t. I think its appropriate to have a little patience – especially if she wanted a second “date”. I’d be careful with what language she used, she really may be in a friends only mode, which is her prerogative considering she’s just out of a relationship – but if she’s cognizant that it is going to be an actual DATE, then everything is going fine. For instance, an anecdote: I was pretty persistent and checking in on a plan a girl and I had to go to a ramen restaurant and have ‘dinner’ together. Turns out, I show up outside her office, as we had planned, and she says she’s in the mood just for drinks and music. OK, that’s fine, I like her so whatever, we go for drinks at a bar with music. And, naturally, we end up having dinner later on that night anyway. Confused? Yeah, so was I. But think about it – having a sit down dinner with a girl can have an immensely different connotation – its closer to our definition of a ‘date’. Just hanging out a bar and drinking, is closer to just….well….hanging out. And that’s how fine the line is for some women. She was absolutely hell bent on making sure there was no pressure of a ‘date’ and that we were just hanging out as friends. But it did suck because I wanted to treat it one way, and she was treating it another way.

    So remember, you can have patience, but sooner or later that patience can wear thin if you put too much investment into it. Sucks to put it in financial terms, but that’s really how it becomes. She eventually has to take the step, but you can’t be stuck in neutral.

    Cautiously optimistic – I think that’s the term here.

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