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troperville

This is a "Wild Mass Guess" entry, where we pull out all the sanity stops on theorizing. The regular entry on this topic is elsewhere. Please see this programme note.

Hitch

Hitch arranged for the jerk at the bar to obnoxiously hit on Sara.

While it appears he just happens to be able to intercede during an unpleasant situation, we've seen him arrange countless other scenarios to bring a guy to a woman's attention. The Grey Goose martini that shows up just as Hitch leaves pretty much proves that he planned it all beforehand.

Hitch had already ordered a Grey Goose martini for Sara before he went over, so this seems a little thin.
- Also his facial expressions as the guy tries his awful pick-up lines are very pained for someone who knew it was going to happen. Likely he just told the waitress to come over with the martini as he left and not before.

Yes, I know, different stories, the movie was first, and this is really contrived. This is just a fun idea.

Hey, It's That Guy! + Mind Screw = What if Michael Westen's mom emotionally manipulated him into doing the craziest inverted honeypot operation in Hitch's vicinity, just to get him to get out of this cynical, loveless career and actually give himself a chance at love? Michael would totally take a Groin Attack for that. Hell, Fiona would probably even be cool with the dalliance. WHERE ARE THE FANFIC WRITERS WHEN I NEED THEM?!?

Actually... Not the craziest idea. Though since this movie, as you said takes place before the pilot of the show, I'm seeing it as more along the lines of Michael being in the middle of a covert op (while still on the government's payroll) and staying in character meant goading Hitch into attacking him. This way he could properly keep up his cover to the other players around him. Painful, but effective.

High School Musical

WMG/Film

The Hobbit