Who was the swimmer Ben is watching at the end? It looked like Madison's brother sans the glasses, but that would make no sense whatsoever (though I suppose that would be consistent with films complete lack of it). Also, are we supposed to take a happy ending away from the film? You can clearly see Ben's girlfriend looking pensive as she holds his hand.
The guy at the end was Randy (Jason Ritter). I thought the ending worked as more bittersweet which was more realistic than all cheery again and back to normal.
Introduce her to your world of sex, drugs and what else do you do?-Kathryn Mertuil, Cruel Intentions
I agree, the ending was more realistic. Ben screwed up, and had to pay the price.
He may have been on probation and had another chance later, but likely he didn't.
He just seemed satisfied his friend was successful, and that he was back with Amy and Madison was out of the picture.
"I'd say this cloud is Cumulo Nimbus."
"Didn't he discover America?"
"Penfold, shush."