I'm going to Mexico this weekend for spring break with my friend and while I'm excited about the opportunity, I'm a little nervous about talking to girls with him. I normally have no problems with flirting, hookups, etc. but he's just coming off a long term relationship, and he seems to be struggling to find that cocky/funny attitude. It comes off as awkward, and it kind of kills my vibe.

I know he's got what it takes, and he's a good looking guy, but he's been out of the game for so long that sometimes it feels like I'm babysitting. Any advice on making us a deadly pair in the field?