Vince Vaughn's had Jennifer Connolly, Malin Akerman, Reese Witherspoon, Isla Fisher and Christine Taylor.
Kevin James' had Winona Ryder, Maria Bello and that chick out of King of Queens.
It always strains my suspension of disbelief when they're cast like this. And then I find out they're both macking some real hotties IRL! KJ in particular - he must have a massive wang or something!
Umm, would you rather watch a movie with Vince Vaughn and Isla Fisher (or any of the other good-lookin' women mentioned), or Vince Vaughn and some random slob off the street? Isla Fisher--you already said it, is incredibly sexy, and most guys would rather watch her than some fugly chick.
Umm... hello, have you seen who Isla Fisher is married to? Borat! FVCKING BORAT! (I'd pick Vince Vaughn over him in a heartbeat!) and Vince Vaughn actually dated Jennifer Anniston, she's hot by most standards. What's so far-fetched about him landing someone like Jennifer Connelly's character?
Besides, women are much less superficial than men when looking for a potential partner. Not a hookup, but an actual life partner. I have seen waaaay too many hot girls going out with average-looking (or even lower-than-average) looking men. Seriously, it's not so far-fetched.
Katy Perry is married to that "comedian" whose name I can't remember. Heidi Klum is married to Seal!
Now, how many men in hollywood are actually married to average-looking women?
---------------------------- WHAT THE FVCK IS A BIEBER????
Women like guys with money, they go for money/security/providers first and looks second. If a guy is funny and has a good sense of humor, that goes even further.
Any man worth millions is automatically disqualified from the "I can't believe she's with him" competition for obvious reasons. How many 26 year old babes would be waiting at Hef's place for him if he worked at Taco Bell?