Gossip Girl
Summary
Serena van der Woodsen was a true icon onGossip Girl , with adating history of boyfriends that was just as complicated as it was exciting . Since the dissolution of her human relationship with Dan in time of year 1 , she has dated a plethora of man , some of whom included her childhood friends , former teachers , con game artists , politico , and then Dan ( again ) .
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When she was n’t looking for Gossip Girl ’s identity element or chart her own unique path in a world of perquisite and traditions , her love life was a major peak of her story on the show . Like most other teens on the Upper East Side , Serena kept a swiftly revolving door of partners , and she liked to mix things up . Serena van der Woodsen ’s significant others in the serial publication were n’t just those in her cockeyed societal rope but include hoi polloi she meet in her travel and some characters who only stayed for a handful of episodes before they moved on .
Blair and Chuck were always meant to be endgame on Gossip Girl , but what about the other men the Queen B date on the show ?
10Tripp Vanderbilt
Played By Aaron Tveit
Serena and Tripp started having feelings for each other while she was working on his campaign , butthe job was that he was married . Tripp tried to keep Serena as a kept woman while the Vanderbilts stayed matrimonial , but Serena did n’t want to be demand in any of it .
Tripp was an dread partner because he lie to Serena , tried making deals with his married woman without her knowledge , and then eventually pass on her in a car stroke to go when he realise that getting caught would harm his reputation . He had no humanity whatsoever and Serena deserve better .
9Gabriel Edwards
Played By Armie Hammer
Some fans might not even remember that Armie Hammer play one of Serena van der Woodsen ’s boyfriends inGossip Girl . While on vacation with her friend Poppy , Poppy ’s fellow Gabriel left Poppy for Serena and followed her to New York . pathetic Serena did n’t know better than to recognize all the red flags and got sweep away in the exoticism of European vacation and sudden romance .
Unfortunately , the intact relationship was a scam , and Poppy Lifton was revealed to have been in on itfrom the beginning . What begin as a ploy to get some money off of Serena ’s moneyed meshing became way too complex , and even though Gabriel did seem to have genuine feelings for the gilded girl , he was too shady at the nerve of it . This was one ofthe saddest matter to happen to Serena , who was naturally swear .
8Aaron Rose
Played By John Patrick Amedori
In time of year 2 , Serena started date Aaron Rose , seemingly for something to do . He was a pretentious artist - type who look at delineation of beautiful women but could n’t bring himself to place to monogamy . This clash tremendously with Serena ’s dating style . Though she ’d had multiple partners in the past , that was n’t something she want any longer .
The only emotion he showed was mild annoying when Serena dared to assume that they were sole before he decided that they were . The kinship was quite inconsequential , ashe only serve as a bargaining tool for Serena to endeavor to get Dan to admit he still loved her .
Blake Lively rose to stardom as in Gossip Girl . However , another major star topology almost beat the role , which would have majorly affected Hollywood .
7Max Harding
Played By Brian J. Smith
time of year 5 saw Ivy impersonate Charlie Rhodes , but her dissatisfied boyfriend made it back to New York to haunt her , and to use Serena as bait . Max seemed like a sweet unseasoned mankind but became spiteful presently after , as often happened with the Serena van der Woodsen significant others who got a crash course in the Upper East Side . It was obvious that his agendum was to get in on the riches of the UES gang , and like many others , he used Serena as an in .
The two dated very in brief , but broke up when Ivy made everyone believe that he was a liar . Theunpopular opinion was that Serenawas too naif to know better , but Max take vantage of her to pressure Ivy , which made him a passably terrible someone . Despite Serena knowing how manipulative those in her social circle could be , she always seemed to bank those with a amorous interest in her .
6Ben Donovan
Played By David Call
Ben was Serena ’s teacher when she was a embarkation school student(and a minor ) . The two had feelings for each other , but never act on them . Though nothing physical ever transpired between them , Lily mould an affidavit incriminate him of statutory rapine , but this bit her later on when Ben and his sis , Juliet , dream up a plan to ruin Serena ’s life .
When Ben was released , he and Serena started a legal relationship . deplorably , there was no clip to unpack the creepy-crawly origins , the harm of being falsely accused and sent to prison house , or the fact that his sister drugged her and place her up . The two dated pretty briefly before it became exonerated that the kinship was too complicated to go anywhere . Ben was bothSerena ’s friend and a threat to herduring his brief clip on the show .
5Dan Humphrey
Played By Penn Badgley
Dan Humphrey is the well - known of Serena van der Woodsen ’s boyfriends becausetheir on - again - off - again romance limit much of their time inGossip Girl . Dan and Serena started dating early on in time of year 1 , but complications like Georgina , their differing social status , and sharing of half - sibling made their kinship extremely mussy . Dan could n’t accept many of her personality traits , which made fans feel bad for Serena .
Despite their knack - ups , Dan and Serena ’s love life persist , even when Dan was very much in love with her best admirer Blair . He could be loving and supportive , but his moments of jealousy and waver trueness proved to be problematic . Still , it was clear that they were meant to be . Despite Dan being uncover as Gossip Girl and torturing Serena for a better part of 6 years , she said she understood him and forgive him before they stop up together in the stopping point .
devotee were shocked when it was revealed Dan Humphrey was Gossip Girl all along . It did n’t seem to make sense , but these clue say otherwise .
4Colin Forrester
Played By Sam Page
Serena run into Colin Forrester by chance , but they hit it off almost instantly . Things were made complicated by the fact that he was her professor , but Colin did seem interested enough in her to stop his forgetful stint as a guest lecturer to be with her . He was genuine and helpful , but his fault was speculative timing .
The two separate up shortly after , mainly becausethis relationship come in the middle of the Dan vs. Nate debacle . Serena could n’t choose between the two men in her life , so she used Colin as a distraction which made this Latinian language fizzle out quickly . He ’s not exactly the most memorable of Serena van der Woodsen ’s significant others as a result .
3Steven Spence
Played By Barry Watson
Being the primary character was Serena’sjob , but it get exhausting . After running away from Manhattan , she met Steven and pretended to be someone else . However , he was mature enough to realize Serena ’s ogre , and accepted her wholeheartedly , despite the sham pretenses under which their relationship began .
deplorably , the Upper East Side and his teen girl Sage had other plans for the match . Sage essay to sabotage Serena at every step and succeeded when she released her sex tape recording . Steven was a adequate man who wanted Serena enough to propose to her , but the play eventually got to him , and he conk out it off .
2Nate Archibald
Played By Chace Crawford
Nate and Serena seemed like star - crossed lovers whenGossip Girlbegan , but their romance was just a teenaged dream . Nate , who always had a affair for Serena , stand by her through every awful choice she made with his cousin Tripp and the backwash of the stroke , which made them realize they wanted to be together . Heseemed like he would have been the perfect final young man for Serena van der Woodsen , but the show had other programme .
Nate had a pure soul , and he always wanted the best for Serena . Nothing could retrain his focus from her , not even Jenny , but Serena left him behind when he called the fuzz on William for giving her imitation Crab . He had the honest intentions but played his cards incorrect . alas , Serena ’s fondness for Dan in the end put an conclusion to her and Nate ’s relationship .
1Carter Baizen
Played By Sebastian Stan
Serena and Carter were actually pretty well - suited to each other : both had scandalous pasts and were n’t particularly trusty , but were trying to be better multitude than others give them deferred payment for . Carter showed up for her when she was struggling with her beginner and sample to determine answers , and he helped her emotionally , which was something nobody else ever did for her .
Carter was a worthy married person because of how self - aware he was . He never harm Serena and tried to make her palpate better at all give points . If his past tense had n’t make out back to haunt him , he may have been her ideal collaborator , and they could have finishedGossip Girltogether .
