Anyone who is part of a celebrity's inner circle has a shot

No matter how "big/famous" that celebrity is (plenty of examples of people like say Britney, JLo or Shania going for the backup dancer or friend's husband, etc).

Albert is already part of Allegra's circle. Her being a client of the firm where he's a junior partner gives him access to her and actually interacts with her (limited and whatnot).

So he can actually talk to her and take his chances without security escorting him off the premises and landing in court for stalking.

Not the same as trying to go for someone you don't get to interact with (say have him have a crush on Beyonce or Britney, neither of whom he has access to in any way/shape/form).

So since he already has access to her, with some help from Hitch he could very well have a realistic chance. If K-fed and Cris Judd could nail Britney and JLo...