Final update from the OP:
It turns out the scene was from Season 4, Episode 1 of Parks and Recreation:
Andy: Hey, so Tom offered me a job again. As my manager, what do you think I should do?
April: Well what do you want to do?
Andy: I think it’d be kind of cool to work for Tom.
April: So take it.
Andy: But working at a start-up can be kind of risky.
April: So don’t take it.
Andy: But Tom told me to follow my dreams.
April: So take it.
Andy: But this isn’t my dream.
April: So don’t take it.
Andy: I don’t know what to do.
April: Me neither.
Andy: You give such good advice. Babe, I love you.
April: You’re welcome.
Thanks all!