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> He's around my age last time I remembered
> We used to be friends in the 8th-9th grade, but we haven't spoke since I transferred schools back in 2021
> Because we haven't spoke in so long, there's a 98% chance he' probably gonna say "no", and for all I know he might have a gf already
> My whole family keeps saying that he's "into me" despite this, and I'm staring to get really fucking tired of it (which is why I'm thinking about doing this in the first place)
> Last time I remembered, he was going through training for the military (I think JROTC, not sure)
> Appearance is average (basically he looks like your typical male high schooler who's in the JROTC)
> Thinking about taking him out to this pizza restaurant near my place (it looks like the perfect spot for a date, at least from what I've seen in the movies)
> Haven't thought of a specific day that I want to do it on since I'm still not sure if I want to go through with this; If i do decide to go through with it though, I will update this post
> Gonna ask one of my other friends IRL about him to see if she has any advice
> I'm pretty damn nervous tbh
> If anyone has any advice they'd like to share, please let me know
> Wish me luck
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Taurus🐂
I think asking him out on a date now is a bit risky since you two haven't talked in a while, you could ask him to hang out first. If you ask for a hang out and not a date there's always an option for you to say that you just "wanted to restory the connection" or something, and you will see if you two really click. If you think the hang out went well ask him out.
But I think the most important thing is that you're asking him out because YOU want to, not your family. If the date goes well he might be YOUR partner, not your family's. So think if you really want to date him or you just feel pressured to do so/feel the need to prove you can do that.
Sorry if it isn't helpful, I'm shit at romance.