This is a bit of a long story but I’ll try to keep it as short as possible –

I (27M) live in the same city as a girl who I went to grade school with and have had a bit of a crush on for 10+ years, since we were in middle school together (was mutual when we were really young but just kid stuff). We haven’t interacted much aside from following each other on social media, etc but a year ago she showed up at a show of mine (I’m a musician) out of the blue. I was dating someone at the time so couldn’t in good conscience go after her, but got her phone number and we followed up briefly afterwards saying we should get some friends together to hang out sometime.

Fast forward to a year later and I’m in a position to finally try and start something with her. It feels really awkward to text her to hang out literally a year later … what do I say? We don’t see each other anywhere or have mutual friends so it’s the only way I could get in touch (that or Instagram, but she doesn’t post much so not many opportunities). Any thoughts / advice on how I should reach out or how I should approach things?

2 comments
  1. Man who cares if it’s awkward. Sure a random text a year later can be a little daunting but who knows, she may have been thinking about you this whole time too. Just be straight up about it. “I was thinking about you the other day and how I didn’t get to know you as well as I would have liked, how would you like to grab a drink with me sometime and catch up?”

    Or something similar. Idk, I feel like taking risks are a huge plus in dating

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