Somebody like Dana (Rose Byrne) would NEVER be available for dating...
Seriously, that was the most implausible aspect of the film, and there were several.
Why? Simple: she's drop dead gorgeous, still young (early 30's), smart (works at Google, right?) and quite polite/fun to be with (not a total douche).
So either she's:
- taken (dating somebody already or married)
- not interested in dating anyone right now (career focused)
Either one, she would just not be available. I mean, she would have guys lining up everyday to ask her out. And not only at work, but everywhere she would go.
That someone like Owen Wilson would be able to pick her up so easily is too insulting. He would have been reported for stalking in real life after their first "random" encounter. Maybe a really smooth talker like Vaughn would be more believable getting away with that, but not Wilson.