Maybe he should pick on someone his own size.
I want the doctor to take your picture so I can look at you from inside as well.
Could be any number of reasons - not all of which have to do with the content of the script... Maybe she just came in, and did the best audition?
"Your mother puts license plates in your underwear? How do you sit?!"
Maybe he's a chubby chaser?
shareThat scene was pretty hilarious actually ... like you said, it was a big surprise a good-looking fellow like Will dated her. On top of that we are learning that she is the one who ended the relation !
However, she seems like a smarter person compared to Will who seems kind of lost without her :
1. She has to bring back his stuff and he doesn't understand it at once;
2. She has to tell him how to take care of his plant;
3. Wiil asking if they are at least still sleeping together xD
Probably a scene to show's will flaws. However, the rest of the movie seems to prove that scene wrong since Will was actually pretty clever the rest of the time.