Context: 26M and 26F

I saw this girl from college (who was a friend) at a basketball game a couple months back, I messaged her and we just caught up over coffee today. It was friendly vibes, but I could tell that she was wondering why I hit her up randomly. I tried to casually say that I was just looking to reconnect with some old friends, work for the team, etc.

Overall, I was reading the situation and she was also giving off friend vibes. But nice and good ones! So I left it at that.

Honestly, I’ll probably never run into her unless I make plans with her, so I’m thinking of shooting my shot regardless. How should I go about it?

I was thinking of waiting a couple days and then messaging her and saying this:

Hey it was cool catching up Tuesday, we might be coworkers next season if I do (the hype squad) 😂
But in all honesty I think you’re a really cool and genuine person, we should grab a drink

Should I keep it subtle like that? Or should I say:

Hey it was cool catching up Tuesday, we might be coworkers next season if I do (the hype squad) 😂
But in all honesty I’ve always thought you were pretty and I think you’re a really cool and genuine person, we should grab a drink

Or neither lmao

6 comments
  1. The second one. Should make your intentions clear, so she knows what she is getting into by saying yes or no. The first one even if she says yes, she saying yes because she thinks it is platonic. It would be a blindside if you suddenly brought up romantic intention.

  2. Sounds a little simp. The first line before the emoji is fine. But I would refrain from the compliments and just say something like – I would love to take you on a proper date and continue to catch up. Are you up for grabbing a drink or maybe dinner later this week?

  3. You are being decisive about wanting to see her and take her on a date. I think it is okay to offer options. You are cool if she only has a little time or is not sure about you and only wants to commit to drinks. Or you are happy to spend more time and money and offer her dinner.

  4. I would cut out the text compliments & just ask if she wants to get a drink. Better but not 100% necessary, if you’re already planning it going somewhere, you can be hey I’m doing xyz, you should join. (Honestly, you can frame it this way even if it’s something you won’t do if she says she’s busy.)

    I thought you meant you were longtime friends right now with the topic, that’s more difficult/not possible sometimes.

    Complimenting women isn’t bad but it’s better if you do it in person, also if you notice some detail that’s not just “you’re pretty.” I mean I’ve called a woman pretty when the conversation is already there, like she changed her hair or something, just about context.

  5. Since your first “date” was just a friendly catch up, your intentions are not really that clear. You need to make it so. There is no need to say “you’re pretty” in a text when you ask a girl out. They know. It’s implied. Why else would you be asking them out? So you just need to ask them out.

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