How do I ask out a childhood friend?

So I grew up with this guy, we were close friends but distanced after he went to different school when we hit high school. Never considered him at all when I was younger but it’s been about 8 years since we were in the same class. (We are both 23 now) The last time I seen him was when I was with my ex about 3 years ago. It was in traffic and he waved me down in the car next to me and we had a short interaction. A couple months ago we matched on tinder but never spoke. I deleted tinder as I started seeing someone. Since we matched he liked every single one of my Instagram posts. Then recently my best friend ran into him on a night out and said he had matured and become extremely good looking. He also told her to say hello to me. I just downloaded tinder again and he matched me again. I sent him a joking message about him looking extremely familiar. He replied saying it was like a high school reunion because he seen my friend the other night too. I replied saying it’s a small world and he didn’t continue the conversation? I’m wondering if I should just let it go or if there is a way I can pick the conversation up because I wouldn’t mind exploring if we potentially have a connection! But I don’t want to come off to intense because I obviously have lots of mutuals with him.



Submitted July 04, 2022 at 01:15AM

So I grew up with this guy, we were close friends but distanced after he went to different school when we hit high school. Never considered him at all when I was younger but it’s been about 8 years since we were in the same class. (We are both 23 now) The last time I seen him was when I was with my ex about 3 years ago. It was in traffic and he waved me down in the car next to me and we had a short interaction. A couple months ago we matched on tinder but never spoke. I deleted tinder as I started seeing someone. Since we matched he liked every single one of my Instagram posts. Then recently my best friend ran into him on a night out and said he had matured and become extremely good looking. He also told her to say hello to me. I just downloaded tinder again and he matched me again. I sent him a joking message about him looking extremely familiar. He replied saying it was like a high school reunion because he seen my friend the other night too. I replied saying it’s a small world and he didn’t continue the conversation? I’m wondering if I should just let it go or if there is a way I can pick the conversation up because I wouldn’t mind exploring if we potentially have a connection! But I don’t want to come off to intense because I obviously have lots of mutuals with him.
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