Obie has a bad track record when it comes to dating. Between causing drama between the sisters and now his issues with Grace, Obie seems to put himself into drama.

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Photo Credit:
Emily V. Aragones/HBO Max
Show:
Gossip Girl (2021)
Network:
Max
Episode:
Gossip Girl (2021) Season 2 Episode 3: "Great Reputations"
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Gossip Girl (2021) Photos, Max Photos, Gossip Girl (2021) Season 2 Episode 3 Photos
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Gossip Girl (2021) Season 2 Episode 3 Quotes

Good evening, followers. For those who might have been living under a rock, maybe you haven't heard. There's a new Queen of Constance.

Gossip Girl

Obie: So, when does Tiff get in?
Grace: This morning. She's taking the train down from Exeter, so I guess, like, 10:00? She's literally the coolest friend I have. I can't wait for you to meet her. Julien: Great! You're here.
Obie: Yeah, and I'm in the middle of a conversation with my girlfriend.
Julien: That's who I was talking to. Hot chai with vanilla sweet cream foam? Grace: My favorite order. How'd you know?
Julien: You mentioned it was your go-to afternoon pick-me-up over New Year's Eve, and I'm a good listener.
Obie: Yeah, because you and Monet were trying to sabotage her.