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How do I know when to stop pursuing someone? Basically, I'm

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How do I know when to stop pursuing someone?

Basically, I'm interested in this guy, but I'll only be seeing him one or two more times unless I do something about it. I feel like we have good chemistry and he's easy to talk to (which is extremely rare for me). I'd like to get to know him as a friend first mainly, but we're only acquaintances at this point.

On one hand, I feel like I've been jumping through hoops/stressing myself out in order to get to the "right" convo/situation with him. He did give me his email to contact him, but I'm pretty sure he was just being polite and even then I don't know what to talk about. On the other hand, I know that if I don't take chances and have some initiative, I won't get anywhere with him, or in life in general. I just don't know when I should say to myself "okay, enough is enough."
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>>17995810

why dont you just ask him to hang out?
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>>17995816
I can try and twist it as much as I want, but at the end of the day I'm just scared he'll say no.
>>
And so what if he says no. You are already living with him saying no. Ask him to hang out , perhaps with a group of friends and have more conversations with him. You'll regret not asking him. Rather to have tried and get a no than live with regret and a possible yes. If it doesn't work out there are plenty of fish in the sea. Get him! Good luck! :)
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>>17995914
Well won't that put you at ease? If he says no it'll sure sting but then you have a definite answer, he's not interested.
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>>17995914

>im scared he'll say no.

he might. only way to find out is to ask. you have two chances left. there is literally no other avice to give other than ask him.

if you just stop pursuing someone when you literally didnt even ask him to hang out, then you never pursued him at all and should probably give up on life
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>>17995940
You (and the others) are right...

Last question. Should it really just be something simple like "Hey, wanna hang out sometime?" The phrasing seems odd to me but I usually overthink these things.
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>>17995977

it can be. it can be something super specific, or it can be in the middle.

i like to talk and then if something i can use comes up, or bring something up, like 'im getting a mad sushi craving right now'. then she says 'OMG I LOVE SUSHI' and i say 'we should go get some this weekend'.
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