This might sound a bit stupid but I don't have much experience in this department, so any thoughts are useful. My best friend just broke up with his boyfriend, who I have a thing for. My bestie knows I have this crush and has said he's totally cool if I want to try and be more than friends with his ex. So I was wondering, if I did decide to act on it, how long do you think it's appropriate to wait before asking someone out after a breakup, and how exactly do you go about broaching the subject?