When do dan and blair date

Dan cheats on Blair with Serena around the same time Blair decides she'd like to leave Dan for Chuck. Dan doesn't give up right away, instead trying to guilt and worm his way back into Blair's life. When she finds out he cheated on her, she goes back to hating him.

Blair and Louis meet in Paris, but Blair returns home before a relationship can develop. Louis shows up in New York months later to pursue Blair. Their relationship is pretty cute at first, what with the fairytale charm of a Prince traveling to return Blair's lost high-heeled shoe. The two are engaged after a brief courtship, and later Blair becomes pregnant with his baby. Blair loses the baby while attempting to flee her engagement with Chuck and ultimately decides to stay with Louis.

She confesses to Chuck that she still loves him on the day of her wedding to Louis. The confession is recorded and sent to Gossip Girl, seen by Louis and basically everyone else. An angry and embarrassed Louis tells Blair, after going through with the wedding, that he doesn't love her anymore.

They stay together until the prenup she signed allows them to divorce. Chuck and Blair However, she has to play referee between Vanessa and Olivia Burke , after they start behaving jealously toward each other after a threesome with Dan.

After Serena is drugged, Blair and Dan work together to find Juliet Sharp and take her down, as well as find out what her motives are for destroying Serena's life. They ask Gossip Girl, who provides them with an address in Connecticut. They go together, and find Damien Dalgaard , who accompanies them on their mission for the rest of the day in The Townie. They find they have similar interests in movies and museums, and begin to secretly hang out.

In The Kids Are Not Alright , Dan calls Blair a dictator of taste when it comes to fashion, which makes her realize that maybe her future lies in working for a fashion magazine.

Blair gets an internship at W Magazine, but is taken aback when Dan also secures one there. They begin to compete, and eventually make a bet that whoever can bring the best author to the W Party that night can stay at the magazine while the other resigns.

Blair calls her author, and Dan calls his, and both can attend. While at work, Blair is given the chance to sabotage Dan but chooses not to. She realizes this is the wrong choice after she discovers he sabotaged her.

The two get into a physical brawl and both are fired. While packing up their desks, Blair admits that she worked hard to get an internship while Dan only had Lily make some calls. After finding this out, Dan resigns so Blair can keep her job Damien Darko.

After Blair quits W Magazine due to it being too stressful, she goes to see Dan at the loft and they order pizza and watch a movie together While You Weren't Sleeping.

In Empire of the Son , Dan and Blair plan to reveal to everyone that they've started hanging out. However, their news is overshadowed by Lily turning herself into the police after forging Serena's signature.

Rufus and Dorota Kishlovsky both think that maybe a budding romance is what's going on, though they both deny it. At the end of the episode, they share a kiss to see if there really are any feelings between them. Chuck, having heard Blair had a life changing kiss, eventually finds out it was Dan.

He sets him up so Blair can see Dan will never be a part of their world, but Blair tells him that she already knew that, and the kiss was only life changing because it made her see that her future lay with Chuck.

She says the kiss meant less than nothing to her, and Dan agrees to save face. Vanessa overhears and leaves Serena a voicemail telling her. However, Serena doesn't believe her. But just to make sure, she makes her newly arrived cousin Charlie Rhodes Ivy Dickens , follow Blair on a secret date just to make sure. She sees Dan and Blair together, and tells Serena.

But when Serena arrives, she sees it's actually Louis Grimaldi and tells Charlie she was probably just confused on who Dan was. Louis is there secretly, and when his family finds out and orders him to come back to Monaco, Blair devises a plan to keep him there. She acts like she's really in a relationship with Dan and Louis has just come to attend the Pink Party. At the party, she kisses Dan and has the picture posted on Gossip Girl.

A jealous Serena realizes Vanessa was telling the truth and informs Blair that the only interest she has in Dan stems from the fact that Serena had him first. Blair, however, defends her friendship with Dan, and that she considers them intellectual equals and they have a friendship on a different level than either have with Serena Petty in Pink. Before she goes, she tells Dan that she copied his Netflix queue and their movie discourse begins the following Monday.

Eric notices the chemistry brewing between them, but says nothing. In Yes, Then Zero , Blair goes to Dan when she's thinking about leaving Louis but becomes angry when she realizes not only was Dan going to let her leave everything with no questions, but he knew Louis was protecting her.

In Beauty and the Feast , Dan is the first person Blair tells about her pregnancy voluntarily. She goes to see him that night, and admits she isn't sure if Louis or Chuck is the father, and Dan promises to be there for her no matter what happens.

But once she receives the results, she decides not to look. After Dorota finds out, she calls Dan, who tries everything to make Blair look. She asks him to 'take her there' and Dan fools her into believing that Louis does not have her best interests at heart, despite the fact that Louis is doing something to help him.

He begins to get ready just as Louis enters the loft. Blair assumes that Louis was following her, and starts reprimanding him. Dan 's conscience gets the better of him and reveals that he tricked her, and the reason Louis was not there was because he was helping Dan with his book issue. Blair soon becomes furious with Dan as he did not tell her the real reason why Louis could not make it and departs with Louis, arm-in-arm, leaving Dan alone.

And at the end of the episode it's been revealed that Blair is the one pregnant. Over the next few episodes, Blair is found having trouble keeping the pregnancy a secret and begins having morning sickness. Things get more difficult when Louis's sister, Princess Beatrice, comes to town. When she hears Blair 's morning sickness in the bathroom, she begins to assume that Blair has gone back to being bulimic.

She decides to invite Blair to a feast to be sure. Meanwhile, in Brooklyn, Dan is still trying to stop the publishing of his book, so that he will not be rejected by his closest friends and family. He calls Serena on the phone and asks her how she went through Lily's bank account so that he can go to Vanessa's bank and look for the publisher, but she tells him that it was all Chuck's doing, driving him to go searching for Chuck.

To his horror, he finds Chuck getting beaten up by a group of men. He attempts to stop the men unsuccessfully, but when Chuck tells them to stop, he reveals that the men were not real criminals and he paid them to hurt him, much to Dan 's astonishment.

This leads Dan to search for Blair and inform her about Chuck's recent dilemma so that he get him the helps that he wants.

Meanwhile, at the feast, Blair begins to feel sick and searches for an excuse to run to the bathroom without arising suspicion. She begins to silently pray to God for a way out, and once she finishes, she sees Dan at the front of the door.

Blair drags him to the toilet and orders him to guard the door. Dan announces that Chuck is getting himself into trouble again, but Blair brushes it off, stating that he's merely doing it to get her attention. Once Dan hears Blair throw up, he begins wonders what is wrong with her and, like Beatrice, assumes that she has gone back to her previous bulimic ways.

He voices out his concern and Blair leaves the wash-room stall, stating that she was not bulimic, but instead pregnant. However, Beatrice walks into the bathroom just as Blair reveals her pregnancy to Dan. The both of them are shocked, but agree to keep it a secret. Afterwards, Blair arrives at Dan 's loft once again, revealing to him that she is uncertain who the father of her unborn child is.

He encourages her to take a test, but she refuses, stating that she'll lose her fairytale if Chuck is the actual father. Dan responds that she will still have him.

However, Blair , being her usual self, still tries to avoid taking the test, but after much persuasion from Dan , she eventually does, and announces that the father is Louis.

She then tells Louis that she's pregnant, much to his elation. Soon afterwards, Serena, Nate, Chuck, Louis's mother, Eleanor and Cyrus all know about Blair 's pregnancy, and she decides not to keep anymore secrets regarding her unborn child. Dan decides that it is time for him to tell Blair about his feelings for her, unrequited or not, when she comes and visits him at his loft, feeling heavy-hearted and dejected. She tells him that she wishes to be happy again, but has forgotten how to be.

After a very emotional phone call with Chuck, Blair enters Dan 's living room heartbroken, looking devastated and emotionally drained. Dan decides to attempt and bring Chuck and Blair together again, as this is what Blair wants. He decides to keep his feelings for Blair quiet and bottled up, only letting Serena know how he feels about her.

Dan leads both Chuck and Blair individually into an enclosed candlelight room. Once they both come face-to-face, Dan closes the door and shows himself out, leaving them both alone. Then, he engages in a discussion with Serena, telling her that it would be wrong to him to reveal his feelings about Blair to her. Serena to tells him that he's one of the good guys. While Blair and Chuck are whisked away in a town car, planning on running away together, Blair decides that she wants to raise her unborn child with Chuck.

They both end up in a serious, life-threatening car accident when paparazzi tail them continuously after Ivy sends Gossip Girl a blast, informing her on Chuck and Blair 's whereabouts. The accident causes Serena, who is alongside Nate and Dan , to be more furious at Gossip Girl then ever before, and blames her entirely for the accident caused.

Dan momentously states that she Gossip Girl didn't jump on one of the motorcycles and chase Chuck and Blair down the road, but Serena angrily responds that the accident is merely the result of all the amount of damage that Gossip Girl has caused throughout the years.

Nate agrees, and he Serena begin planning on taking Gossip Girl down for good, to avenge Chuck and Blair. In the next episode, Blair learns that she lost the baby in the accident, much to her depression and despair, and she immediately bursts into tears when the news reaches her. She becomes even more terrified when Serena tells her that Chuck is in serious danger, due to losing a large amount of blood. This drives her to make a secret deal with God, promising Him that if he saves Chuck's life, she would marry Louis and not go back to being with Chuck.

Once she makes the promise, the nurse informs her that Chuck is asking for her. She decides that this means that God has honored their promise, and chooses to further her relationship with Louis, so that Chuck will be safe, as she couldn't bare losing him. She informs Dan about her deal and tells him to keep it a secret, to which he agrees, so that he will get to spend more time with her. Soon, only Dan and Serena know about Blair 's promise.

She begins avoiding Chuck and Louis, who collaborate to find out what was going on with Blair, and find pictures of Dan and Blair together in New York, learning that the only man she's not avoiding is Dan Humphrey. Dan goes with Blair to her wedding dress fitting, and she gets upset due to the fact the the dress shows everything she has lost. Dan tells her that she should change her mind about marrying Louis, but she insists on pursuing the wedding, stating that she is committed to him.

Both Louis and Chuck think that Blair must be having an affair with Dan , as this is why she is so distant with everyone but him.

They worry about her, and when asked if she is indeed having an affair with Dan , she immediately denies.

Soon later, she finds Louis's wedding vows, and is pleasantly stunned with how accurately he describes her and how much love the vows display. She tells Serena that she feels as if Louis had "Peered into her Soul" , and now is happy with the decision she had made, believing that Louis is the one for her. However, unknown to Blair , Dan was the one who wrote the vows, after Louis asked him to. For some reason Dan went ahead to write them although it was assumed that it was for Blair's happiness sake.

During the wedding day, Chuck and Blair confront each other once again, and Blair declares that she does indeed love him, she loves him more and more everyday, but cannot be with him. She leaves the room to attend the ceremony, leaving Chuck alone in the room.

Cyrus and Harold both give Blair away, and Dan and Serena walk down the aisle together. However, it appears that Georgina has taped a Chuck and Blair 's moment, when Blair was professing her love for Chuck.

It was assued that Chuck was in possession of the videotape that was sent to Gossip Girl. It sends Blair running down the aisle, first wrongly accusing Chuck of sending the blast in that ruined her perfect day.

She explains to Chuck that although she loves him she cannot be with him due to the pact she made with God. Louis appears at the door, and Blair apologizes for embarrassing him, returning to the alter soon after to continue the wedding. After Louis and Blair say their vows and take each other as man and wife, Serena tells Dan that she loves him, that she always had and she always will, just before Louis and Blair take their first dance as a married couple.

As Blair tells Louis that she's very thankful for giving her a princess title and especially grateful that he gave her another chance, he coldly responds that their wedding was all for show and there is nothing but a contract between them.

He tells her that when they're alone, they'll become like strangers to each other. Blair calls Dan and tells him to pick her up outside the venue. Blair tells him that the wedding was a sham and she asks him for help to get out of the country and file for a divorce. They'd spent ages being enemies before eventually interning at W magazine together. But against all odds, the Upper East Side princess and Brooklyn hipster had great chemistry. Blair and Dan brought out each other's intellectual sides — they could talk about classic movies and visit art exhibits together.

And aside from their intellectual similarities, Blair and Dan were always just twisted enough to work with each other. They're both manipulative, but neither of them was ever straight-up evil. Dan also seemed capable of getting over his Serena Blake Lively hangup when he was with Blair though she was never fully over Chuck, even when she was with Dan.

He even wanted to help Blair raise her baby! They could have helped each other move on from unhealthy relationships, which would have been better for everyone; instead, they both ended up in questionable marriages. Also, Dan and Serena have a half-sibling!