The characters on Gossip Girl have a pretty low overall success rate when it comes to their many, many relationships. They often jump right into things before finding out important information, like that their parents were in love, or that one of them is being paid by a third party to feign interest for some mildly nefarious purpose.
Because of this, their track record with first dates, unsurprisingly, aren't all that great. From mildly awkward to truly disastrous, these dates are definitely the worst.
10 Dan And Serena
Dan was psyched to finally get a date with Serena, whom he'd had a crush on for years. He took her to meet his dad first, which was pretty awkward. They still manage to enjoy each other's company, but their date is cut short when Jenny texts Dan asking for help at the Kiss on the Lips party.
They find Jenny on the roof being accosted by Chuck, who Dan punches before they get Jenny out of there. As first dates go, it's pretty disastrous, but Dan still manages to charm Serena enough to get a second date.
9 Dan And Serena (Again)
Dan and Serena's second first date (they decided the first one didn't count) started on the wrong note, with Dan showing up dressed for an evening much fancier than Serena had anticipated. Next, Serena mistakenly believes that the Vespa sitting outside of her apartment building was rented by Dan for their date. Dan waits until she's finished gushing over his thoughtfulness to point to the Towncar behind the Vespa that he rented for their date.
He takes her to a fancy restaurant that he can't afford and makes lame jokes the whole time. None of his attempts to impress Serena work, and he's horrified to learn that Serena paid for the meal before he had the chance. Once Serena tells him that he doesn't need to impress her with an expensive meal, Dan relaxes and they manage to turn the night around. Unfortunately, their date is once again interrupted, this time by Serena's younger sibling.
8 Dan And Amanda
While on the rebound from his second breakup with Serena, Dan asks new girl Amanda out on a date after they bond over their love of writing. Fans never get to see how their first date goes, but their second date is memorable enough to discuss as one of the most terrible dates on the show.
Serena is offended by how quickly and publicly Dan has moved on, so she third wheels with them on their second date. The night becomes all about Dan and Serena's issues, so an upset Serena orders Dan to take his date and leave. They don't leave fast enough, and Blair's minions give Amanda a Nair-tini.
7 Dan and Lexi
Aaron's ex-girlfriend Lexi comes to town the day before the Snowflake Ball, and Dan asks her to accompany him after they hit it off. Serena's mostly fine with it until she finds out from Aaron that Lexie might want to sleep with him.
The idea of Dan being with someone else really bothers Serena, and doesn't bode well for how the dance will go. Serena tells Dan about what Lexi might be thinking, and his reaction upsets her, even though she is being completely disrespectful to the other girl. The two end up spending the evening talking to each other about their first time together, which doesn't exactly bode well for Dan's first date with Lexi.
6 Serena And Gabriel
Not sure if this totally counts as a first date, but Gabriel's pursuit of Serena after their vacation (with his ex-girlfriend, Poppy Lifton) leads him to barge into, and subsequently be invited to stay for Cyrus' Seder.
Serena doesn't want to see him, so she lies and tells him that she's back together with Dan, who is catering the ceremony. Awkward hilarity ensues, and it becomes clear that Serena's lied. She finally comes clean and admits her feelings to Gabriel.
5 Blair And Cameron
Blair's first date with Cameron is interrupted when Dan and Nate approach her for help with a plan to unearth the truth about Rufus' supposed infidelity. He ends up following her around while she teams up with Chuck, her most recent ex, on an elaborate scheme.
Cameron isn't present for the grand finale, so Blair spends her evening with Chuck. He picks her up at the end of the night so that they can continue the date they'd had planned, but it's clear that her thoughts are still with Chuck.
4 Blair And Louis, Serena And The Fake Prince
Blair is excited when Louis asks her out on a date, thinking he's the Prince of Monaco. When he shows up driving the "real" prince, her fairytale dreams of a life of eternal luxury are shattered. To make matters worse, she takes a phone call from her mother during the date and finds out that Serena, who's there on a double date, is going to be attending Columbia with Blair in the fall but failed to tell her.
She tells Serena off and leaves the restaurant. Serena follows her in an attempt to bring her back, so Blair shoves her into a fountain and goes back on her own. Louis then reveals to her that he is the real prince, but that he was posing as a driver in order to ascertain whether Blair was only interested in him because of his title. He's disappointed in how she treated him when she thought he wasn't royal, and leaves her by herself.
3 Dan And Charlie/Ivy
For Dan and Charlie's (who is really Ivy) first official date, she shows up dressed and styled exactly like Serena was at the debutante ball (which she sort of went to with Dan). Charlie proposes that they have sex in Headmistress Queller's office, but Dan puts a stop to things when Charlie asks him to call her Serena. She then gets really drunk and starts embarrassing herself and Dan.
When it's clear that she's completely screwed things up, Charlie heads to the top floor of the building, threatening to jump. Serena finds her and talks her off the ledge, but by that point, the date has been an absolute disaster and the season ends with Charlie leaving town.
2 Nate And Charlie/Ivy
Blair holds a competition to choose her bridesmaids, and one item on the agenda is kissing Nate. Charlie, desperate to win the competition, exploits Nate's desire to make Diana jealous and proposes that he take her as his date to a Spectator party. They're having a good time, and they seem to actually be into each other.
Charlie kisses Nate in order to make Diana jealous, which works, but also makes the two realize their feelings. When Nate finds out Charlie used him for a competition, it makes things less genuine. Overall, the date is much too complicated.
1 Serena And Max
Serena meets Max, unaware that the woman he's traveled to New York to find is her cousin (who she also doesn't know isn't really her cousin), Charlie. She's smitten by... something and decides to ask him out on a date that night.
Diana uses this as an opportunity to break up Charlie and Nate and sneaks Max by Serena. Serena waits for him all night but thinks he never showed up. This is the only date where neither party ever actually interacts.
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December 07, 2020 at 02:30AM
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Gossip Girl: 10 Worst First Dates The Characters Had | ScreenRant - Screen Rant
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