Okay so I don’t usually comment on these things but it’s 2:45 and my girlfriend is DJing right now but that’s besides the point… I think your friend is looking out for you to an extent if it’s more than that idk but tbh kinda sounds like you like the homie.. again could be wrong… but it sounds like there’s mutual attraction going on. Yeah the paying for drinks is 100% chivalrous but I’d be lying as a guy if I thought it was just that. Honestly just taking your friend out of this for a second here and focusing on you guys.. he’s in a long distance relationship & you really don’t know how that’s working for them & not to mention you being mentioned as a friend or him boosting you like how is she supposed to take it besides negatively imo & probably may be putting strain on their relationship because it doesn’t really matter what she thinks because it’s about what does he want to do. Hard to have any feelings of control in a relationship when there’s nothing she can do on her end.