Do you think I should text him even if it's out of the blue?
Should I text him? I like my brother's friend.
Do you think I should text him even if it's out of the blue?
i'd be so nervous. but I'm guessing since nothing has happened so far, he may not really like you like that. several years is a long time for nothing to happen. id get my brother to set something up. like he could just get some insider info for you. it would be weird to get a text from someone you didn't give your number to. I'm not saying its a bad idea, just might not be the best method. at least try to hang out with him and your brother, and get your brother to see if its worth the trouble. he's your brothers friend and apparently isn't going anywhere so you have to think about how it would be if you started flirting and he didn't like you. it could get awkard but you have to be the judge of that. it could be alright either way.
Yes you'll regret it and always wonder if you don't.
Yes.
Pick on him, or say you're going to happy hour at _____ and you'd like it if he bought a round for once.
Sass and nonchalance.
There's only way to get to know someone. And that's talking to them. You do the math.
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2Opinion
Initially ...try to assess the situation through your brother...that would be a safe play here.
No. You can damage the relationship with your brother, and certainly end your brothers friendship with his friend.
There are like 3.5 billion men on this Earth. Find another one.
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