My buddy with the fedora is really just looking for friendship first. He has a lot of female friends. Saw a girl with a cool shirt, brought it up, and they spent the hour talking and pretty sure they're doing coffee dates now and moving into something more.
Where my brother who is a gym rat goes around asking literally every woman under the sun if they want to have dinner. I watched him go up to the bartender, ask her out, get rejected, then while walking to the bathroom, get rejected by a girl waiting in line in the bathroom. He calls it a numbers game and is oblivious of how he sees women. Also yuck when he asked out the bartender.