Before that Halloween picture I would have said probably not but after that picture where
1) She is dressed in a costume that says I am getting laid tonight one way or another
2) She is hanging off of him
3) They are all smiles as is Anna
Not that I expected Anna to go off on him but I thought the the first time he was out on a date in front of her it was going to be like when he ran into Mac, a wee bit awkward. Since it doesn't seem to be and since he seems to do whatever Britt tells him I could see her seducing him and him going along.
Anyway I think he might sleep with Britt now and when Robin returns Britt is not happy about it.