There's just one question I want to pose today: Where is Aunt May really going?
I don't know about you, but I don't buy the whole "getting together with friends from work" thing. You get that dressed up for a work get-together? She's definitely seeing some one, but who? Two possibilities leap to my mind:
One, it's a member of Nick Fury's staff (like an accountant or something) dating Aunt May to get her in trouble and further mess with Peter's life. Because, you know, Nick Fury gets his kicks from stuff like that. Heck, Fury is probably in charge of Deadpool and his Mutant Loser Brigade. And now I'll stop before I start ranting.
Two, she's dating J. Jonah Jameson. I can't remember if he's married in this continuity, but if he isn't, their mutual distrust of Spider-Man could be a connecting point. Jameson may not believe Spidey is evil anymore, but he has (understandable) questions about someone who swings around in a weird costume punching people. And Aunt May, well she made her feelings pretty clear when Peter was going to tell her he was Spider-Man.
Plus, I can recall at least one or two occasions where May put Jameson back on his heels, particularly when JJ offered Peter the job at the Bugle. Jonah seems to like/respect people who aren't intimidated by him. Ben Urich is constantly giving him crap, but Jameson lets him because Urich gets results, and because Jameson trust people who don't let him push them around, up to a point. So that may make her intriguing to him.
Seriously, how badly would that mess with Peter, his boss dating his aunt? He might be better off with the "Nick Fury is trying to mess with you" option.