The friendship between Chuck Bass and Vanessa Abrams.
Overview
'A Connection..."
A tumultuous, opportunistic, and fleeting relationship occurred between the characters Vanessa Abrams and Chuck Bass sporadically across Season 1 and Season 2. Their short-lived relationship originated from Blair Waldorf's attempts to protect Serena's affections of Dan Humphrey. In doing so, a hostility grew between them, thus intertwining Chuck Bass to sometimes intervene on behalf or because of Blair. What started out as an opportunity of circumstances became a mutual respect for each other. In the few episodes of Season 2 they developed a further connection with each other from social interests and family problems that were revealed. Chuck's initial interest in partaking the purchase of a run-down Brooklyn Inn was the result of a Blair scheme to take-down Vanessa for another video-tape blackmail. Chuck took a genuine interest in purchasing the Inn thus surprising Vanessa as her 'miracle.' Unfortunately, Bart Bass quickly vetoed the idea as a naive venture.
'Stay for Me?'
Concurrently, an update to Blair gives hints to a change of affections from Chuck. This causes Blair's insecurities to awaken. She then directly confronts Vanessa with the truth. Abhorred, but not showing it, Vanessa says she does not want to be part of their game. Chuck then takes the firm action of explaining the truth to Vanessa but is stone-walled at the Inn.
Ironically, Vanessa's own mentality changed later the season when her own insecurities, alongside with Chuck's, became an issue with their respective relationships with Nate and Blair. Vanessa schemes a plan make their intermittent partners jealous by going to the party together, but after realising that they did not faze them she then kisses Chuck in front of them to provoke a response. Later that day, Chuck awakens to have slept with Vanessa and sometime afterwards. This was revealed during a candid conversation with Dan.
Personalities
Pretences???
On a general glance, Vanessa and Chuck share little in common in personalities or interests. But beneath their public facades they both share a distaste for social conformity and disadvantages. When it comes to both schemes and social interests they believe in charity for others + steadfast convictions to see through with a plan. As a result, they rarely think of the consequences of their actions before acting on them. They also share a degenerate personality when trying to express themselves to each other. This of course led them to having a sexual relationship with each other. It is also mentioned that although they have convictions of following though with their schemes, they often feel great guilt for their part. Almost immediately they would either take a tactical retreat or try their best to fix the situations that they have irreparably created.
There are hints and confirmations that Vanessa has partaken a perchant for schemes as a a result of Chuck's presence in her life.
Novel Series
In the Novel Series, Chuck Bass has no interaction with a Vanessa Abrams as they are not in a relationship with each other. Vanessa does share a on/off again frienenmy relationship with Blair Waldorf whom she befriends or sabotage on occasions.
TV Series
In the television series, both Vanessa and Chuck share a short fling and sexual relationship with each other. This predominantly occurred in Season 2, but their foundations were set in Season 1.
Season 1
Cause and Effect from Blair
In Season 1, episode 11 Roman Holiday, Vanessa encounters the first wrath and suspicion of Blair Waldorf when she places interest in helping Serena gather the perfect gift for Dan Humphrey's birthday. This is the beginning of a type of rivalry between Vanessa and Blair which later causes her to become attracted towards Chuck Bass.
The first real encounter that Vanessa has with Chuck is in Season 1, episode 12 School Lies, whereby Vanessa intercepts a revealing conversation between Blair Waldorf and Chuck Bass's indiscretion at the pool and their 'limo night.' Mid conversation, Chuck requests that Vanessa hand over the incriminating evidence, but a protective Dan allows her to exit. Initially, Blair makes first attempts at negotiating the recovery of the tape but in vain gets ignored by Vanessa. Chuck takes a second attempt for the tape by tapping the shoulders of Vanessa and asking for it for a handful of cash. Although, he comes off as chauvinistic it appears that he succeeded in persuading that Vanessa could truly need the money to live by. What he failed to realize was that Vanessa handed over a fake tape. It is hinted that Vanessa might have started a medical grant in Chuck Bass's name for genital herpes. It is also hinted that Vanessa enjoyed the banter with Chuck.
Season 2
"I'm Chuck Bass"
In Season 2, episode 7 Chuck in Real life, Blair once again feels antogonized by Vanessa when she blackmails to help her send flyers to the Upper East Side with another incriminating video tape. Later, Blair uses her flirtatious relationship with Chuck to ask him to pretend to purchase a Brooklyn Inn. He agrees stating that it can be in the mutual interest for both parties to take down the 'two birds' (Dan and Vanessa respectively).
Vanessa is somewhat happy with the turn around at the 'speakeasy' rally event for the Inn. That is until Chuck Bass turns out at the event with his limousine. He outlines his business proposal which is oddly well thought out. Nevertheless, Vanessa is hesitant in believing him; much less the crowd as he is 'slushied' for his efforts. Humiliated, he takes a tactical retreat from a whisky Vanessa.
However, Vanessa does come over to Chuck's place when Horace
Gluck Slushie Moment
receives the contract for purchasing the building. She is impressed that he has included the addendum that the building will not be replaced or taken down. Thus, she is willing to vet him to meet Horace to talk it over despite her misgivings. When meeting Horace Rogers, the owner of the Brooklyn Inn, he discovers a rapport with him that cements that he might be the Inn's saviour. Chuck himself sees the potential of the run-down Inn being a nice addition to Bass industries. Displaced from his initial motivations he walks outside with the full intent of purchasing the inn. Vanessa is grateful but also flabbergasted that their miracle came in the form of Chuck Bass. Feeling guilty Chuck is about to explain the truth to Vanessa, but Blair's text leaves him to invite Vanessa over to a party. It is left unsure if this was ploy to continue Blair's plan in taking down Vanessa or a genuine invitation to the Upper East Side (UES).
While at the party and ignoring Blair, Chuck welcomes Vanessa, but he is taken away for a candid conversation from Bart. Vanessa takes this moment as victory against Blair in gaining Chuck's affections by glancing at her direction. With Blair's insecurities tipped she decides to back down from the scheme. As for Chuck and Bart's conversation, Vanessa overhears that Bart Bass has no intentions to approve the purchase of the Brooklyn Inn even though Chuck himself fully endorses the contract. Bart scoffs off 'What is the value of Chuck Bass's promise?'
In a private room, Vanessa confides in Chuck that it is not his fault and she contemplates on how hard it has being raised with a father like Bart. Regressing, he states that she can not possible know what type of person he is and defends his father actions as a wise decision. However, Chuck's actions betray his words, and he asks Vanessa to stay for his sake. An onlooking Blair is convinced that there is definitely something going on between her and Chuck.
Confronting Vanessa with the truth, Vanessa disagrees with Blair justifying Chuck's good character from what she saw from the conversation and explaining that perhaps Chuck is better person when not around her. Unfortunately, when cornered, Chuck's silence confirms the existence of the scheme, thus revolting Vanessa; although she keeps a brave face. Chuck returns to find Vanessa at the Brooklyn Inn, but is blocked by Horace who is disappointed in Chuck's character. Vanessa stares onwards from the passing Chuck thinking about his gesture.
The 'Epic' Kiss
In Season 2, episode 20 The Remains of J, Vanessa coyly thinks that she is reuniting back together with her boyfriend Nate Archibald after a disagreement / break with him. A text from Chuck Bass affronts Vanessa in seeing an exchange hug between Blair and Nate. Naturally, Vanessa is egged by Chuck to investigate the validity of Blair and Nate's friendship. She asks Nate about his whereabouts at the morning to which he lies. Vanessa and Chuck are insulted and thus collude a plan at Eric's party. While inside of the elevator, Chuck is mildly impressed and attracted to Vanessa's attire. They banter back and forth but Vanessa wants to stay on task. When exiting the elevator they are left dumbfounded at the casualness of Blair and Nate's presence with each other. As a result, Vanessa face-holds and kisses Chuck passionately who fully reciprocates. Clearly having an effect, both Blair and Nate try to make them jealous in the bedroom upstairs. While waiting, Chuck jokes that their overwhelming chemistry should put a wedge between their minds. In fact, it does when Blair considers Nate's true intents while making out. Blair and Nate decide to start afresh as a couple. It is also revealed that Vanessa and Chuck have slept with each other. Vanessa conveys to Chuck that it meant nothing to her to which he agrees, but their actions are betraying their words as they continue to kiss while narrating to Gossip Girl.
In Season 2 episode 21, Seder Anything, Vanessa and Dan Humphrey play a game of "I Never" to which it is revealed that she slept with Chuck Bass. Dan is repulsed, but quickly contests that she has been under the ringer this year. But Vanessa takes another sip when admitting to sleeping with Chuck twice. Thus, committing to further repulse Dan.
Wakey, Wakey...
Season 3
In Season 2, Chuck Bass and Vanessa Abrams have little if not no interaction with each other. However, as Chuck is supporting Blair Waldorf at her time at New York University (NYU) he indirectly is confronting Blair's insecurities that are partial to both Georgina and Vanessa who fit better with the student cohort.
Season 4
Vanessa has no interaction with Chuck Bass as her character is no longer a main character, but a recurring character.
Push and Pull...
Season 5
In Season 5, episode 18 Con-Heir, Chuck sets up a foundation for disabled kids under Jack Bass's name in a New York hospital Wing. This could be an allusion to Season 1 episode 12 School Lies whereby Vanessa hinted in setting up a grant under Chuck Bass's name for genital herpes.
Quotes
Season 1:
Gossip Girl: Now that sex and lies have been caught on videotape.... V's documentary just became the most anticipated new release of the year.
Vanessa: What that, your stripper money?
Chuck: Yes I do, I know girls like you. You act like money's not important, but money's important to everyone.
Chuck: Blair's an amateur. She thinks you just like her. To Blair, this money is a couple pairs of Manolos and a Chanel bag. But I know that this much cash can make a real difference in your life.
Vanessa: You're sick. Chuck: You're welcome.
Blair: Oh, and one more thing. If you didn't pay your rent with it, what did you do with Chuck's money? Vanessa: I may have created a medical grant for teens with genital herpes. In his name.
Season 2:
Chuck: I knew you (Vanessa) were more like me than you let on.
Blair: The only person Vanessa loathes more than me, is you (Chuck).
Vanessa: Here comes the shark (Chuck's limo drives inwards).
Chuck: I'm Here Because of You (shows the poster for the speakeasy rally).
Vanessa: I knew it would take a miracle, but I never thought it'd be Chuck Bass. Chuck: Vanessa, there's something (explaining he's initial reasons)....
Vanessa: Maybe what's going on is you can't stand that he (Chuck) might actually... ... be a good person when he's not around you (to Blair).'
Vanessa: Hey. I overheard the end of that conversation... and I'm sorry. I don't know your dad, but from what I saw today, you deserve better. Chuck: You say that, but you don't really know me. Chuck: Stay, Please (grasping and holding onto Vanessa).
Vanessa: But it's been all day is sleazy platitudes and... [Chuck is gawking] ... you staring at my boobs. Chuck: I came up with several excellent ideas, you just shot most of them down. Vanessa: Yeah, the all involved leaking a Chuck-Vanessa sex tape to the internet. Chuck: We don't have to leak the tape if you don't want to. Consistent. Twisted.
Vanessa: What do we do? [Kisses Chuck Bass]. Gossip Girl: (Spotted): Two people who should know better... and two people who don't know what hit them.
Nate: Is he your boyfriend? Vanessa: We're not a couple. Just physical.
Chuck: You just need to relax. Trust in the power... ... of our overwhelming sexual chemistry to drive a wedge between them.
Gossip Girl: But every mistake happens for a reason: To teach you a lesson you would otherwise never learn. .. And hopefully we never make that mistake again. Lucky for me that never happens. XoXo Gossip Girl.
Vanessa: I never slept with Chuck Bass [Big Gulps, Dan looks weirdly puzzled]. That why I've been avoiding you. I know it's repulsive. Dan: It is completely repulsive. But you've been going through a lot lately... ... I mean, the whole Blair-Nate reunion and all... plus the whole looking up and looking down thing really has to appeal to it. So you get no judgement from me. Everyone makes a mistake at least once. Dan: I never nearly slept with Georgina Sparks. [Both Chuckle]. Vanessa: I never slept with Chuck Bass twice. [Gulping a second time] Mm. Mm. Vanessa: Dan you're lucky. However bad your life sucks right now, you didn't need an STD panel this week. Dan: Wait, why does my life suck right now?
