The relationship between Lily and Rufus, also known as Rufly, is the relationship between Lily van der Woodsen and Rufus Humphrey. Possessing a relationship which predates the beginning of Gossip Girl, Lily and Rufus get married in Season Three but their marriage was declared invalid in the fifth season.
In the series finale, Lily and Rufus become in-laws when Dan and Serena get married
In Pilot, Lily visits Rufus at his new art gallery. They question and tease each other about their lives, and when Lily leaves she suggests that Rufus stays out of her life. She has begun a not so secret relationship with Bart Bass whereas Rufus Humphrey's wife, Alison, had been having an affair while living in Hudson doing art. Eventually, the two become friendly again and old sparks begin to fly. At Thanksgiving, it's revealed that Rufus and Lily dated before Rufus met Alison, and she was his fist big love and Alison hates Lily for this very reason. Lily left Rufus to be with William van der Woodsen after CeCe told her to pick between Rufus and her inheritance.
Meanwhile Dan, Rufus' son, and Serena, Lily's daughter, started a relationship, and this ultimately brings Lily and Rufus together once more. In The Handmaiden's Tale, Lily, wanting to make Bart Bass jealous, brings Rufus to Eleanor's party and the two kiss. When Jenny brings Alison home, things get complicated. Eventually the three talk everything out, with Rufus and Alison deciding to work on their marriage and cut Lily off. However in Roman Holiday, Rufus and Alison realize things aren't working after Alison's Hudson boyfriend Alex asks to meet her, and when Rufus goes instead and finds out she never ended things. They decide to separate, and at the same time, Bart proposes to Lily. She doesn't give him an answer right away, and is about to choose to be with Rufus when Serena begs her not to because she doesn't want to be a stepsister to her boyfriend. Lily accepts Bart's proposal.
On the night of Lily and Bart's rehearsal dinner in Woman on the Verge, Lily and Serena end up at a concert Rufus and his band Lincoln Hawk are playing at. The two end up having sex that night. The next morning in Much 'I Do' About Nothing, Bart tells Lily that sometimes you need to let old things from your past go. Rufus comes to see Lily before the wedding, and while they admit they love each other, Lily ultimately chooses to marry Bart.
Season 2 Edit
Lily feels as if Bart isn't very attentive and very secretive, including hiring a PI to look into her past. She tries to be friends with Rufus, although he's not very keen on the idea, and is dating other people but he eventually comes around. In It's a Wonderful Lie, Lily is again torn between Bart and Rufus. However, when Bart is on his way to confront Lily about it, he dies in a car accident. After the accident, Lily relies on Rufus to support her through it. The two decide to go on a trip to figure things out but before they can leave, CeCe tells Rufus that many years ago, Lily had his baby and gave it up for adoption. Angry at not being told, Rufus tries to find the child on his own. Eventually, him and Lily take off to Boston to find him. They meet with the adoptive father, who tells them that Andrew, their son, had died in a boating accident.
When Bart's brother Jack Bass comes to town, Lily adopts Chuck to avoid Bass Industries going to Jack. However, Chuck is still angry at Rufus and Lily for the role they played in the death of his father. Soon after Bart's death, Rufus and Lily come out as a formal couple. But the problems that have always haunted their relationship soon come out: the difference in class and worlds. Rufus is uncomfortable in Lily's high society world, but ultimately decides that he loves her enough it make it work.
When Dan is accepted to Yale, both him and Rufus were expecting decent financial aid. When he's denied and can't afford it, Lily offers to help pay. Rufus refuses, and decides to take matters into his own hands. He debates selling the loft, but instead chooses to sell the gallery because he doesn't love selling art anymore.
When Serena accidentally involves herself and her family in a ponzi scheme and the participants lose hundreds of thousands of dollars, including Dan's college money Rufus invested with, Lily decides to deal with it the adult way and pay everyone back with her own money. Wanting to help Dan with college, she decides to pretend everything worked out and send Rufus money behind his back. However, Rufus finds out and is humiliated. When Lily has Serena arrested to get her away from attempting to deal with the situation herself, it's the last straw for Rufus.
In the season finale The Goodbye Gossip Girl, Rufus and Lily make up and he proposes. She says yes.
Season 3 Edit
In the beginning of the season, Lily is with CeCe and Rufus has spent the summer with Eric, Dan, and Jenny in the Hamptons. Serena decides not to go to Brown, and while Rufus is at first skeptical on the choice, he comes around. When Lily returns, she becomes angry at Rufus for not making Serena go. The two argue and take a break. In Rufus Getting Married, they make up and decide to get married immediately. The plans work out and everything has come together, when Lily gets cold feet and almost backs out. They talk and are interrupted by Georgina, who tells them Vanessa's new boyfriend Scott Rosson is actually their son, and that his adoptive parents lied to Rufus and Lily about their son being dead. They catch up with Scott, they all talk and have a happy reunion, and get married that evening at the loft.
At Thanksgiving in The Treasure of Serena Madre, Rufus finds out from CeCe that her supposed sickness was cured by August, not October when Lily came home. Lily lies to Rufus when confronted, and says she spent extra time with CeCe because her mother had become kind and she wanted to enjoy it. Rufus believes her. At the same time, Serena is having an affair with Nate's Congressman cousin Tripp van der Bilt, and his wife Maureen finds out. When leaving the VDW penthouse, she accidentally takes Lily's coat, since she has the same one, and finds a letter Serena's dad wrote to her. In it, he tells her that he couldn't see her during the summer because he was with Lily. When Lily realizes the letter is missing, she goes crazy trying to find it. In order to distract Rufus, she sends him to a rooftop garden committee meeting where he meets Holland Kemble. Meanwhile, Serena is blackmailed by Maureen into ending the affair with Tripp, but her efforts to avoid anything happening are stopped when they get into a car accident and Tripp leaves her. Maureen goes to see Rufus and gives him the letter.
In The Hurt Locket, Rufus returns from a ski trip and refuses to talk to Lily. Eventually, he confronts her and she admits to kissing William but tells him nothing else happened. Rufus is more upset at the fact that Lily lied about where she was and that she kept the secret for so long. He leaves and ends up at Holland's apartment.
When Jenny is caught with Damien Dalgaard in her room, Lily calls Rufus who decides to move Jenny back to Brooklyn with him. When he went to see Holland, he left his scarf there and she gives it to the doorman, Vanya, who brings it to Lily. She gives it too Rufus, and when they talk later, they decide to start over with a clean slate. That is, until Lily lies to Rufus about going to Canyon Ranch with CeCe, when she's actually going to see Dr. VDW.
Carter Baizen tracks down Dr. VDW and when Serena finds out, they go to find him together. Before they reach the airport, Serena ditches Carter, who was trying to get her away from Nate. She goes to his hotel and is surprised when Lily answers the door. At the same time, Rufus finds out Lily was never at Canyon Ranch and calls CeCe, who gives him no information.
Lily and Serena return to Manhattan, and Lily is finally ready to tell Rufus the truth: that CeCe was never sick, and she was the one with cancer. William shows up at the penthouse, and this causes tension with Rufus. Meanwhile, Serena is lying to William about the kind of person she is, but eventually comes clean. William also reveals he bought an apartment in the building, but Rufus orchestrates the board to not approve him. At an event where he is being honored, William declares he is still in love with Lily and is willing to do whatever he takes to get her back. Also, Holland tips Serena off that she slept with Rufus. It's revealed that Lily isn't sick anymore, and that William is using Holland to give her fake antibiotics.
Chuck, who loves Lily as his own mother, struggles dealing with the idea of her being sick. When Jenny discovers that her meds aren't helping her, the two set off to expose Dr. VDW. They team up with Nate and Blair. Serena believes her dad can do no wrong, and doesn't believe them. After a long scheme, they find out that William sent Serena a letter after she came to see him that he was with Lily, hoping to cause problems with Rufus and Lily. When that didn't work, he tried to get Holland to befriend Rufus but that didn't work either, since his relationship with Lily was too solid. In Plan C, he cures Lily when she's actually sick and he falls in love, but learns from Holland that they're too strong, and in order to get the love of his family back, he needs to save Lily's life. He gets pills from Holland that mimic the symptoms of Lily's cancer, so he can magically cure her again. The plan works, and Lily and Rufus are no longer together until Holland decides to ruin his scheme for she had fallen in love with him and couldn't handle seeing him with another woman. Lily sees this, and befriends Rufus once again.
Season 4 Edit
Lily gets arrested and sentenced to house arrest after forging Serena's signature on an affidavit. Rufus has to care for her and stay with her and they mainly watch Downton Abbey and movies. All through Season Four, they stay together and happily married.
Season 5 Edit
Lily and Rufus start to have trouble in their marriage after Ivy's true identity is discovered. Rufus takes pity on Ivy, and Lily believes she is a worthless criminal. How the two manage the situation ultimately causes a divide between them, which leads to a temporary separation. When Chuck is able to bring Bart out of hiding, the issue of Lily technically being married to two people arises. She has to annul one of her two marriages. Rufus, not wanting to give up on Lily, gives annulment papers to Bart behind Lily's back. When she finds out, she decides that her marriage with Rufus isn't really a marriage anymore and she ends their relationship. She chooses to renew her vows with Bart, and Rufus moves back to Brooklyn.
Season 6 Edit
Ivy, who is dating Dr. VDW, enters a fake relationship with Rufus, intent on taking Lily down. Rufus is onboard with dating her until he sees her leaving a restaurant with a man, and breaks up with her. Lily and Rufus are at odds for awhile, until Rufus brings Lily proof of Bart's illegal oil trading and she burns it so no one can use it against them, and they make amends.
In the five year time-jump seen in the series finale, Lily has reconciled with her first husband, William van der Woodsen, while Rufus has begun dating the singer Lisa Loeb. Rufus and Lily's relationship has seemingly come into good standing, with the two acting friendly to the other and giving each other a peck on the lips at the wedding of their children, Dan and Serena.