So I (21f) recently bumped into an old school friend (21M) that I hadn’t seen in years. Back in secondary school/college we were good friends and got on really well. He also liked me at the time.

Flash forward to a few weeks ago, we bump into each other on the train and realise we now always take the same train. That same day we just went to sit in the park as we hadn’t seen each other in so long and ended up spending 3 hours talking and laughing. This has become a regular thing so now every time we see each other we spend hours just catching up and walking around. I think I’m starting to develop feelings for him after spending so much time together.

Sadly today he told me that in a few weeks / next month he’ll be moving house & naturally we won’t be having these walks together anymore. I want to tell him how I feel before he moves but I genuinely have no idea where to even start.

All the dating experience I’ve had is either high school relationships or online dating, none of which put me in a position of asking someone out.

There’s also a slight complication as he is relatively good friends with my old secondary school / college boyfriend who I broke up with nearly 2 years ago. This of course makes me a lot more nervous that he’ll reject me but I feel like it was just a secondary school relationship & nothing overly serious.

I guess I just need some guidance on how to do this. In person or over text? Is it even worth telling him? Do i tell him i like him or just ask if he ever wants to hang out outside of our random encounters? What do I even say? How do people do this?! I really need all the help I can get lol I’m so lost and bloody nervous.

TLDR: im developing feelings for an old school friend and i dont know if/how i should ask him out

3 comments
  1. The worst he can say is no.

    The worst you’ll feel ever is playing the ‘what if’ over and over.

    Do it. Do it and either succeed in glory or burn in ashes. Life’s too short to wonder away happiness.

  2. How far is he moving away?

    Just shoot your shot. “Hey, I really enjoyed hanging out with you recently and would love to keep spending time together even if we can’t sit in the park like we do right now. Do you want to go on a date some time?”

    Worst that happens is he says no, moves away, and you don’t see him again.

  3. I don’t think it’s so much that you don’t KNOW what to tell him. I think it’s more that you’re nervous to do so because you think the way you tell him will determine whether he says yes or not. it doesn’t.

    You told me everything in the 2 mins it took me to read your post, so you clearly know how to use your words.

    >is it even worth telling him?

    Lol, of course!

    >Do i tell him i like him or just ask if he ever wants to hang out outside of our random encounters? What do I even say? How do people do this?

    Lol first off, don’t beat yourself up for overthinking it. It’s perfectly normal.

    I think you need to re-frame how you’re thinking about this. Think of it this way: Instead of wondering what to say, when to say it, how to say it, just explain the situation to him. That’s it.

    Say: “Hey, XYZ, I have a dilemma… ” and EXPLAIN the situation to him.

    I mean, worst come to worst and you forget the English language in that moment, you could even just show him this post, lol.

    Best of Luck!

    And definitely keep us updated

Leave a Reply
You May Also Like