The one that got away
Deleted because this was stupid to post. I was a dumbass
Sorry my dude but you had several chances to seal the deal and it didn't go down. Good reengagement is not going to do much. You're best bet is to leave her alone and focus your energy elsewhere, maybe you'll bump into her down the road and you can go from there.
Just a side note..when you were walking that girl home you shouldn't have felt awkward about bumping into the other girl. You could have had simply said. "This is my friend (name), what are you up to?" I've never had that happen to me honestly, but I do bring different girls around friends all the time and I never try to justify that I'm going on dates with multiple girls I just introduce as her being my friend and go from there! Guys and girls hangout there is nothing weird about it.