It’s good for couples to discuss their previous relationships. It builds trust. But for Serena Van Der Woodsen, that type of honesty is best kept under wraps. She is, after all, the girl who slept with her best friend’s boyfriend and made a sex tape in the same night. On Monday’s Gossip Girl, “Portrait Of A Lady Alexander,” Serena and Steven put their past love affairs on the table.

The Players:

Episode Title: “Portrait of a Lady Alexander”

Chuck continues to investigate his father’s dealings, and ends up at an event with Manhattan’s elite. Serena and Steven reveal their romantic histories, but neither is prepared for what they uncover. After Dan takes his stories elsewhere, The Spectator‘s in jeopardy and Nate makes a difficult decision to keep it in business. Meanwhile, Georgina pushes Dan towards dating to boost his image, but he’s drawn in a different direction.

The Good:

  • Serena Reveals Her “Floozy” Past: Once Steven brings up previous relationships, Serena freaks out. She has so many skeletons in her closet. Her sexual history was a major problem when she was dating Dan. But since, hasn’t really been an issue. Now that she feels like she’s found “the one,” it makes sense for the writers to bring up her past. This was bound to happen. Lily had to come clean with Rufus a few seasons ago, and like Serena, hid a few details (which Rufus later discovered). We love how history keeps repeating itself. What will Steven do once he gets word of Serena’s sex tape?
  • Chuck Is So Close: We’ve mentioned that the most exciting story (these days) is Chuck’s efforts to uncover his father’s secret. Last night, young Bass got very close. It turns out Bart might’ve faked his death to avoid federal prison because he was (allegedly) buying foreign oil. This is huge. If Chuck gets enough proof, he could put his father away for good. But it’s not that simple. Chuck is kind and decent. He’s not his father, and in the coming weeks, we’ll see what he’s made of. Revenge is sweet, but is Chuck willing to go all the way?

Best Lines:

  • “Maybe your father’s secret is just that he’s into horses, really, really expensive horses.” – Blair
  • “Well I heard they lost a fortune in Facebook stock.” – Blair
  • “But Natasha is a Coppola and that does come with a certain cache.” – Georgina
  • “Well this is what we need! Quick Call the CIA or the FBI or TMZ! Let’s turn him in.” – Blair

The Bad:

  • Is Nate Playing Dirty?: Nate is always having trouble with The Spectator. When it’s not money, it’s content or credibility. We get that Dan’s move (publishing in Vanity Fair, instead of The Spectator) harmed the paper, but there are tons of other writers living in New York City. It’s hard to believe that Nate can’t find someone else. And is he playing dirty? We’d hate to see him go to prison for the same reasons his father did. 
  • Serena Overlooks Steven’s Past (With Her Mother): It’s hard to believe that Serena would overlook Steven’s sexual past with Lily. This is just a big no no, right? Are we crazy to think it’s gross for a mother and daughter to have shared a man? We don’t think so. 

Overall:

It seems like Serena and Steven are serious, and Sage  is on board with their relationship. Having Serena reveal her past is important, but are we to believe she’s OK with him hooking up with her mother? Serena might look like a free-spirit, but she’s actually conservative when it comes to relationships. As for Chuck, him and Blair still make an excellent team, and together they are going to uncover Bart’s mystery. We just hope the secret is as shocking as everyone’s setting it up to be.

Rating: 6.5/10

Gossip Girl airs Mondays at 9 p.m on the CW.

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What did you think of last night’s episode of Gossip Girl?