Should I ask him out?

He must like you too, guys don't have there friend look out for info unless they like you as well. and what do you have to lose? Just ask the guy you like out for a cup o' joe.

You you went out for coffee with ''the guy you like'' bestfriend (because you are friend with this bestfriend). So you are having coffee and he asks you should hook up with that other guy (that you actually like).

If I understood correctly.
He is probably checking do you like his friend (as you do). . So it will be easier for that guy to ask YOU OUT.
At least that's how I see it.

okay, here's how this should go down for you. DO NOT EVER ASK A BOY OUT, that's such a turn off! like, really. what guy wants to have a girl do the thing that he's supposed to do? if anything, you could ask him to HANG out, but I'd stick to just that. And trust me, if you have enough fun, and show him who you really can be, and he likes you, he'll ask you out. BELIEVE ME, I've done this millions of times. And, okay, if his bestfriend is talking to you, the guy might be trying to get his bestfriend to get ya'll together. trust me.