YMMV / To Rome with Love

• Anvilicious: Leopoldo's storyline and its extremely unsubtle satire of modern celebrity culture. At one point, Leopoldo is flat out told that he became "famous for being famous", just in case the audience didn't get it already.
• Hilarious in Hindsight: Monica's graphic retelling of her supposed lesbian affair, which comes across as a blatant grab for attention/attempt to get Jack's interest more than anything else. A couple of years after the movie was released, Elliot Page first came out as a lesbian, then eventually as a Transgender man. Which also fits this trope, as earlier in that scene Monica was retelling her doomed attempt at seducing a gay man.