Honestly, Cutter being wary around women makes Annie want to start sneaking up on him just to see if he jumps or does something weird. She's like that. And Simon has no plans on 'trying anything funny'. He doesn't really see himself as attractive and would never bother a straight guy anyway. It's a wrong thing to do.
Frankie: Annie thinks he looks cool and his act is interesting. She'd want to play with his snakes. The reptile snakes. Not... a metaphorical snake... You know. Anyway. Simon would generally avoid him. One of those Bad Feelings sort of things.
Ella: Annie says that if they both were any sort of lesbian, Annie would want into her panties. Not even gonna lie. As it is, as long as Ella doesn't mind the fact that Annie's a sarcastic know-it-all bitch, they'll get on like peaches and creme. Because of her influence though, Simon feels its best to avoid her... for now. Eventually though he's likely to have a relapse without his adoptive parents to guide him through sobriety.
Esther: First of all, lol. We did fun things with names on this one. Annie Boleyn and H/Esther Prynne fun tiems. Aaaanyway, as long as Esther doesn't push any religion on Annie, she'll be tolerant. As soon as there's a lecture though, she'll get pissy. I don't really see Annie as sticking to one religion. She's been all over the Middle East and Asia so she's created her own hodgepodge thing although she's a big fan of Kama... Simon would be kind to her and tolerant. After all, it's her opinion and who is he to claim that her opinion is wrong? Neutral zeeeeen.