This is now the 3rd night they've slept together and with the excess amount of groping he's done with her I find it hard to believe that she's been sleep through all of it, not unless she becomes 100% comatose during her sleep sessions. I think this guy MAYBE could have better luck if he actually made some kind of move on her instead of waiting until she was sleep to start feeling her up. I can understand after one night, but after all this time this guy has no confidence and Ana is almost entirely about confident guys.
As for her and Dax, if they are in fact done Ana will have no problems finding someone else. I'm not entirely sure she was ready to jump into another relationship to begin with. This guy was actually 3rd guy she had fucked since she broke up with her boyfriend, 4th if you count the BJ's she gave to Dean.