There is a woman in my city that I’ve met once about two years ago, coincidentally on my birthday at the bar I work part-time at. I finished my shift and was sitting down at the bar — she had gotten stood up and I was going through a rough breakup at the time, and we kind of just commiserated and hit it off for a few hours. Nothing else happened although I could tell there was some tension, I just wasn’t in the headspace to try to date or anything else at the moment. Since then, I have seen her on dating apps occasionally but never in person.

Fast forward two years and she came in on a date while I was bartending. She looked completely different, and I didn’t recognize her at first but she kept making eyes with me and smiling. It looked like their date went well enough and after he left, she came over and asked if I remembered her and I said yes. We caught up a bit, and I told her I never got her number before, but it would be cool to hang out. She smiled and said “you want to hang out? that sounds great!”.

So, I am a horrible texter. I’d rather not make small talk over the phone. I also feel as though I don’t want to just ‘hang out’ with her. I think I’d like a chance at dating her, especially since I realize she’s dating. I also don’t want to come off as clingy or desperate, but I did text her the next day to say hello and made a reference to something we talked about, however she wasn’t very responsive to it, so I let it be. At this point, should I just ask her out on a date proper? Like, “I want to take you on a date?” Or what? I feel like my timing is off.

Thanks for any advice.

TLDR; met a girl again after a few years, she was on a date, got her number afterwards. How should I approach this if I’m interested in her?

2 comments
  1. First dates are often a “hang out” anyway. Ask her to coffee or a meal. At that time, get to know her more. If all goes well, you can express your intentions to take her on a “proper” first date and ask her out then.

  2. You’re overthinking it.

    Just throw her a friendly hello and ask if she’s dating right now (she may appear to be, but it’s good to give her an opening to say she’s open to dating) and if she wants to get together this week or next week.

    Then take it from there.

    “Hey! So I saw you with that other guy and I don’t want to overstep or anything. But if you’re not like… with him or whatever, I wanted to see if you want to meet up somewhere with me this week.”

    Something simple like that.

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