Gossip Girl, Season 1

Nate:
Where's the girl?

Chuck:
In my dreams, I was trying to get some shuteye. What's on your mind?

Nate:
It's my mom.

Chuck:
Sounds Freudian.

Nate:
She wants me to give Blair her ring.

Chuck:
What? You guys broke up.

Nate:
Yeah, I know. I mean, wait, how did you know?

Chuck:
Predictably, your ex ran the old, uh, grill-the-best-friend play. Tried to find out where your head was at. So uh...where is your head?

Nate:
Spinning. I mean, my mom wants me to get back with Blair so Eleanor won't pull out of their business deal. It's all cause of my dad's whole trial thing, you know?

Chuck:
Hey, I'm sorry about all that. But look, if you're done with Blair, be done. Don't cave to your parents wishes if they're not your desires.

Nate:
Excuse me? Where's my boy? Seal the deal, tap that ass? Money marries bigger money?

Chuck:
Look, I care about three things Nathaniel. Money, the pleasures money brings me and you. I'm just trying to have your back here. Your parents have been controlling you your whole life, if it doesn't end now, when will it ever?