Episode
| Moment
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Remains of the J
| Serena is introduced to Poppy's boyfriend Gabriel, and he claims to recognize her from that night she went out with Georgina. She was roofied that night so she doesn't remember meeting him. Serena, Poppy and Gabriel head to Spain together.
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Seder Anything
| S and Gabriel hit it off in Mexico after Poppy and Gabriel break up and Poppy leaves.
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Seder Anything
| There is a brief marriage scare, which turns out to just have been a fun, drunken night out. They decide to date anyway.
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Southern Gentlemen Prefer Blondes
| Serena really likes Gabriel, although he can't seem to commit to plans. Chuck and Blair become suspicious about Gabriel after inquiring about the night he met Serena.
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| Southern Gentlemen Prefer Blondes | Gabriel comes clean (partially) to Serena by telling her that he can't tell Poppy they are over because his business contacts are all through her. When Chuck and Blair scheme to get Gabriel, Poppy and Serena in a room together, Gabriel "chooses" Serena but later we learn he is in cahoots with Poppy and it was all just an act.
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| Southern Gentlemen Prefer Blondes | With S's help, Gabriel charms the pants off Lily, Rufus and some other high society types and gets them to invest in his Ponzi scheme, though S still thinks this is a legit business.
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| Southern Gentlemen Prefer Blondes | S becomes suspicious of Gabriel and upon further questioning, she realizes he was lying about the time they met. She takes off, and when she comes back she sees he is nowhere to be found. |
The Wrath of Con
| S is desperate to get the money back , so she calls Gabriel and tells him she thinks she might be pregnant.
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| The Wrath of Con | They meet up, Gabriel confesses to having only gone after Serena for being the daughter of the late Bart Bass's wife. But he claims, now he really has feelings for her. Thankfully she tells him she is not interested.
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