Megan [about Charlie]: When all is said and done, he's my best friend in the whole world and I have to say goodbye
Will: And what I'm saying is you've already kissed your best friend goodbye

Will: I'm sorry I told you to ditch your family. The woman I fell in love with could never give up on anybody
Megan: did you just..?
Will: That's right, I love you Megan Smith. Deal with that
Megan: I love you too

Megan: Cancel the check!
Will: The bank's closed
Megan: You're a billionaire, isn't there a special number you call?
Will: Yah it's 1-800-im-rich
Megan: That's not even enough numbers

Will: I'm just trying to be respectful here
Megan: Respect is for grandmas. I want naked and stuff

Will: So what happened tonight? You got pretty enthusiastic with the vodka
Megan: That was not the plan
Will: There was a plan?
Megan: Well yeah. I thought we'd, you know, have a few drinks, get a little loosely goosey. I kept drinking when you kept drinking and you're much bigger than I am and all of a sudden I got very loose very fast.

I do know that part of being a good boyfriend is listening... and big presents never hurt either

Will: I want a second chance
Megan: It'd be a third chance, the balcony was your second
Will: I want a third chance

Megan: What are you doing climbing up my balcony?
Will: In my head this was romantic, but now I see that it's just creepy. And for the record, you're on the ground floor so there wasn't any climbing involved

Will: You don't have to worry, this isn't a rebound thing. I've been out with a few women since lily and I broke things off. So by definition...
Megan: You rebounded.. and scored. Look at me using the sports metaphors!

Will: I've been refilling your coffee for over a year now peter, you never had a problem with it before
Peter: I didn't know you wipe your ass with my paychecks before. I'm sorry, was that too blunt?

Will: I work for Peter Friedland, he's a sports photographer
Megan: Hey, like you!
Will: Like me, except he gets paid and published and all that good stuff

Megan: My friend Karen is flying in from new york and she's going to stay with me the next few days and I was hoping you could show us some of that rich ass Palm Beach living. You know maybe we could take a spin on one of your yachts tomorrow afternoon
Will: How many yachts do you think i have?
Megan: Okay well if the yachts unavailable, we can go for a ride on one of your horses or elephants.

Privileged Quotes

Boss [about Megan's hair]: It's just so bright
Megan: Everyone loves Lucille Ball but no one does anything about it.
Boss: This isn't about the hair, though it is really distracting...

Hey lady, i can see your va-jay-jay!

Random kid