2000’s movie like Shallow Hal

I vividly remember a movie from the early 2000’s about this guy and his friend, who are both relatively unattractive but reject girls for the smallest things. Guy 1 meets an “ugly’ girl, and he takes her on a date on some boat. I just remember the friend going “It speaks!!!” when the girl says something. And I can’t remember any names of the actors, just the the friend, guy 2, has short curly black hair and he’s quite geeky. I initially thought the main actor was Dax Shepard, but I believe he just looked kind of like him, at least in my memory… If anyone has any kind of information, even with how little I’ve provided, I’ll finally be able to stop trying to find this movie lol. Cheers.

could the friend be jason biggs?
edit: saving silverman?

Okay, wait… The actor kind of looks like Samm Levine from Sydney White, even though looking at him, he looks exactly like who I’m imagining in the movie… But I don’t see the film anywhere.

glad we could help. was the correct answer “barely legal” or “hottie or nottie”?