Guy is definitely fearless in his approaches. You could view his style as awkward, but it fits his personality. I think he used to be a standup comic. You could also view it as screening girls who he would have a good time with. It seems like he approaches enough that screening out the ones he wouldn't have fun with wouldn't be a problem.
Does come off as a bit of an entertainer, but he doesn't come off as try-hard.
Does come off as a bit of an entertainer, but he doesn't come off as try-hard.