"I let you go on your wedding day because... I was afraid I couldn't give you what you needed. I wasn't sure what I needed. And I have regretted it every day since."
-Rufus to Lily, It's a Wonderful Lie
Lily and Rufus originally met years before Pilot and had engaged in a serious romantic relationship while Rufus toured with his band, Lincoln Hawk. However, Lily's mother, CeCe Rhodes, strongly disapproved of their relationship and threatened to take away Lily's inheritance if she didn't break it off. Fearful of losing her money and mother, Lily left Rufus but discovered she was pregnant soon after. She gave birth to a son, Scott Rosson, whom she gave up for adoption.
The two began speaking again when they learn their children, Dan Humphrey and Serena van der Woodsen, have begun dating. They become friends again and realize they still harbor feelings for one another. They begin dating again and eventually marry in Rufus Getting Married. However, Lily later chooses Bart Bass over Rufus and annuls their marriage in The Return of the Ring. They eventually become friendly again and are both present at Dan and Serena's wedding in the series finale time jump, New York, I Love You XOXO.
Television SeriesPilot, Lily goes to see Rufus after she learns her daughter, Serena, is going on a date with his son, Dan. She warns Rufus to continue staying out of her life as she has a new boyfriend, Bart Bass, and she knows his wife, Alison Humphrey, is away from the city. However, they begin hanging out again and she eventually lets him in on the fact that her son, Eric van der Woodsen, is in treatment after a suicide attempt (Dare Devil). Later, she invites him to a party hosted by Eleanor Waldorf in order to make Bart jealous. They go together and they kiss, which leaves both unsure of their feelings for one another (The Handmaiden's Tale).
On Thanksgiving, Dan invites Serena, Eric, and Lily to the Humphrey dinner when he learns they have nowhere to go. When they arrive, Lily is shocked to discover Alison has returned. During dinner, it comes out that Rufus and Lily used to date and Lily and Alison dislike each other for that reason. Afterwards, Alison tells Rufus that they cannot fix their relationship if Lily is in his life and as a result, Rufus chooses Alison (Blair Waldorf Must Pie). However, Rufus and Alison choose to divorce in Roman Holiday and Rufus leaves Lily a message saying he misses her at the same time Bart proposes to her. Lily doesn't give Bart an answer at first, and she decides to be with Rufus until Serena asks her not to, in order to continue her relationship with Dan. Lily, wanting Serena to be happy. stands Rufus up and accepts Bart's proposal (School Lies).
When Jenny Humphrey begins misbehaving and disobeying Rufus, he turns to Lily for advice on how to handle her antics. Lily advises him on parenting daughters and they begin speaking civilly again. Later that night, Georgina Sparks outs Eric as being gay and Lily calls Rufus to tell him about the evening (All About My Brother). In Woman on the Verge, Lily helps Serena overcome her role in Pete Fairman's death. As she lied to Dan about several things to cover it up, she asks Lily to take her to a concert where Rufus will be performing because Dan will be there. Lily obliges and witnesses Rufus perform. Afterwards, he chases her down and kisses her; despite knowing she's marrying Bart the next day. They sleep together and wake up in a hotel together in the season finale Much 'I Do' About Nothing. Bart calls Lily wanting to meet and when they do, he tells her that he needs her to give up Rufus so they can make their marriage work. At the wedding, Rufus shows up while Lily is getting ready and asks her if marrying Bart is what she really wants to do. She affirms that it is, and they admit that they love each other but can't be together. He wishes her luck and she marries Bart.
Over the summer and into the fall, Rufus begins dating women; most notably one named Claire. Meanwhile, Lily is unhappy in her marriage to Bart and tries to seek a friendship with Rufus to fill her loneliness void. However, Rufus doesn't want to get into the middle of her marriage and tells her to stay away from him (The Ex-Files). In The Serena Also Rises, Lily discovers that Bart had his PI, Andrew Tyler, investigate her thoroughly and that he has files on her entire past. In The Magnificent Archibalds, Lily learns that not only does Bart keep files on her, he also has ones for Serena and Eric. Shocked at this, she leaves the apartment on Thanksgiving and spends the evening with Rufus, Dan, Jenny, and Vanessa Abrams.
Soon after, Lily decides she wants to leave Bart to pursue a relationship with Rufus. However, she gives Bart one chance to redeem himself by escorting her to The Snowflake Ball when he returns from a business trip to Miami. He promises to be there, and also assures her that he fired his PI. Before the ball, Lily learns that he lied about firing Andrew and goes to the ball without him. Once there, she sees Rufus and they begin hanging out; a sight that enrages Chuck Bass, Bart's son. He calls Bart to inform him about what's going on and advises him to come as soon as possible. However, Bart gets into a fatal car accident on the way there and dies at the hospital he's taken to (It's a Wonderful Lie). After Bart's death, Rufus becomes a shoulder for Lily to lean on, a fact that stuns Lily's mother, CeCe. She warns Lily to stay away from Rufus, but learns that Andrew is planning to sell Lily's biggest secret to the highest bidder. Lily asks her to pay him off, and CeCe lies that she did. However, Andrew ends up selling the information to Chuck and CeCe takes it upon herself to reveal the secret to Rufus: that many years ago Lily became pregnant with his baby and she gave it up for adoption. Later that night, Rufus reveals to Lily that he knows about their child (O Brother, Where Bart Thou?).
Angry that Lily never told him, Rufus goes on search for the child himself. However, he is unsuccessful and goes to confront Lily about it. She admits that the baby was a boy and the two eventually decide to go to Boston together to find him. Meanwhile, Dan learns about the child from Chuck and struggles with not telling Serena. Rufus tells him not to say anything, as the secret isn't his to share (In the Realm of the Basses). In Gone with the Will, Rufus and Lily sleep together and reminisce on their past. Afterwards, their son's adoptive father agrees to meet with them. At the meeting, he reveals that their son, Andrew, died in a boating accident. He promises that Andrew was a happy kid who loved life; but it's later revealed by the adoptive mother that Andrew wasn't their son and they would never share their real son with them due to being scared of losing him. Soon after, Lily and Rufus come out as a formal couple at the opera (You've Got Yale!).
In Remains of the J, Rufus learns that Dan will not be receiving any form of financial aid at Yale. He confides this fact to Lily, who offers to help him financially. He turns her down and decides to sell his art gallery, as he no longer enjoys selling art (Seder Anything). Meanwhile, Serena has begun dating a con artist named Gabriel Edwards, who manages to scam Lily, her friends, and Rufus for Dan's college money (Southern Gentlemen Prefer Blondes). When Serena learns what happened, she tells Dan and attempts to fix it herself. Worried for his future, he tells Lily, who orders Serena to stay out of it. She plans to pay everyone back herself except for Rufus; who she plans to give money to monthly secretly. While planning to propose in the apartment, Rufus stumbles upon her list of people to pay back and realizes what she was going to do. Embarrassed, he cancels the proposal and goes home, especially after he sees her have Serena arrested (The Wrath of Con). In the season finale The Goodbye Gossip Girl, Rufus and Lily make up and he proposes to her. She accepts.
Lily spends the summer with CeCe in California while Rufus spends the summer in the Hamptons with Eric, Dan, and Jenny. When the three return to Manhattan and meet up with Serena, she asks them to hide her antics from the summer; including when she steals a horse from the annual van der Bilt polo match. Rufus pays off the photographers so that Lily won't see the photos. Soon after, Serena decides to defer from Brown University and asks Rufus not to tell Lily so she can herself (The Freshmen). Meanwhile, Vanessa has begun dating a new guy, named Scott Rosson, who is Lily and Rufus' child. While he doesn't reveal his identity at first, he does to her eventually. She encourages him to tell Rufus and he almost does, until his adoptive mother comes to New York. Upon seeing her, he instead introduces himself as Rufus and Lily's son's brother. He then leaves town and refuses to promise Vanessa that he'll reveal his true identity one day (The Lost Boy).
Lily returns in Dan de Fleurette and becomes upset at Rufus for not forcing Serena to go to Brown. This causes a rift between the two of them and they plan to postpone their wedding. When Serena learns that they're fighting, she enlists Dan, Jenny, and Eric to help parent trap them into talking. After an argument, they realize how much they love each other and plan to get married the next day. While preparing for the wedding, Lily finds herself unable to write her own vows. Before the ceremony, she takes Rufus aside and confesses that she couldn't write her vows. She also admits that she's scared of their future together and Rufus tries to coax her into going through with the wedding. Unbeknownst to the two of them, Scott overhears their argument and confronts them about not getting married. Lily berates him for his rudeness and he leaves the venue. Georgina then emerges and reveals who he really is to Lily and Rufus. Shocked, they flee the wedding to track him down. They find him at the bus back to Boston and the three share a hug. Lily and Rufus end up marrying that night at the loft (Rufus Getting Married).
On Thanksgiving, Rufus invites CeCe to dinner to surprise Lily. During the meal, he discovers that Lily lied about her whereabouts during the summer. When he confronts her about it, she lies that CeCe's illness had turned her into a kind and loving person she wanted to spend time with. Rufus accepts this and apologizes for doubting her story. Meanwhile, Serena has begun having an affair with Nate Archibald's cousin, Tripp van der Bilt. Lily strongly disapproves of their relationship and orders Serena to end up. Serena is prepared to do so until she discovers a letter Lily hid from her father, William van der Woodsen. She then leaves with Tripp and Lily hides the letter in a jacket pocket. However, the letter is discovered by Tripp's wife, Maureen van der Bilt, and she plans to use it as leverage to end the affair (The Treasure of Serena Madre). When Lily discovers the letter is missing, she cleans the closet several times but doesn't find it. As a way to distract Rufus, she sends him to a rooftop garden committee meeting and he befriends a neighbor named Holland Kemble. Later that day, Serena and Tripp get into a terrible car accident which leaves Serena hospitalized. While Lily goes to see Serena, Maureen goes to the penthouse and gives Rufus the letter from William; which reveals that he was with Lily over the summer. When he realizes Lily lied to him, Rufus leaves town to go on a skip trip (The Debarted). In The Hurt Locket, Rufus returns but still doesn't want to talk to Lily. However, they briefly reunite when Jenny begins dating Damien Dalgaard, the drug dealing son of the Belgian ambassador (The Lady Vanished). They later decide to forgive each other for all their wrongdoings and start with a clean slate. However, CeCe calls Lily to tell her it's time for another round of treatment and Lily lies to Rufus that she and CeCe are going to Canyon Ranch for a short spa trip (The Sixteen Year Old Virgin).
Meanwhile, Carter Baizen tracks down William and tells Serena, who agrees to go with him and force her father to see her. However, when she arrives in Florida, she finds Lily inside her father's hotel room (The Unblairable Lightness of Being). She then learns that CeCe was never sick and Lily is the one with cancer. The two travel back to Manhattan together and discover William has beaten them to the apartment and is waiting with Rufus there. Lily then reveals her secret to Rufus, who encourages her to find a new doctor. Serena suggests they stay with William and Lily agrees (Dr. Estrangeloved). Soon after, William invites them all to a benefit where he is being honored. While there, he gives a speech and alludes to his desire to win Lily back. Realizing Rufus was right about his intentions, Lily begins to distance herself from William. However, Holland finds Serena that night and reveals that Rufus cheated on Lily with her (It's a Dad, Dad, Dad, Dad World). Soon after, Serena outs Rufus for cheating in front of everyone and Lily is shocked. Despite the revelation, Dan, Jenny, Nate, Chuck, and Blair Waldorf team up to find out William and Holland's true intentions. After some investigative scheming, they learn that the two were working together to split up Rufus and Lily; and their scheme included diagnosing Lily with nonexistent cancer and Holland claiming she slept with Rufus. Meanwhile, Jenny has become unhappy with life on the UES and tips William off that everyone is onto his plan. Not wanting to face the repercussions, he asks Lily, Serena, and Eric to come back to Florida with him. Before they can leave, they're confronted by everyone but William is able to flee before the police show. As a result, Rufus and Lily realize they were being messed with and reunite (Ex-Husbands and Wives).
In the season premiere Belles de Jour, it's revealed that Georgina gave birth to Dan's baby, Milo Humphrey, over the summer; a fact that Dan is hiding from Rufus and Lily. However, this doesn't satisfy Georgina and she brings the baby to a luncheon hosted by Lily. Dan follows and has a talk with Rufus about the situation. Rufus asks for a DNA test and Georgina answers that she had one done and that Dan is definitely the father. They call the doctor, who confirms the results himself, and Dan signs the birth certificate. Despite this, Rufus still doubts Dan's paternity and voices his concerns to Lily. Soon after, Lily takes it upon herself to create a nursery at the loft for Milo and warns Rufus not to waste his grandson's childhood on conspiracy theories. Rufus takes this to heart and goes to help Lily, who is overjoyed at his decision. But while they create a baby book for Milo, Rufus learns that there is no way Dan could biologically be the father due to the difference in blood type (Double Identity).
In The Townie, Serena comes to the conclusion that Lily forged her signature on a document that sent her former teacher, Ben Donovan, to prison on false rape accusations. Meanwhile, Rufus learns that Lily is planning to sell Bass Industries behind Chuck's back. When Serena confronts Lily about her perjury, Rufus also confronts her about the secret sale. She tries to explain that she wasn't trying to hurt anyone but he admits that he can't believe anything she has to say. However, the two make up and Rufus agrees to help her take down old Bass enemy, Russell Thorpe, who wants to take down the Bass' anyway he can. After an incident between Damien and Eric, Damien informs Russell about Lily forging Serena's signature and being guilty of obstruction of justice (While You Weren't Sleeping). Russell uses this information to his advantage and plans to blackmail Lily with it. When she finds out, she turns herself in, with Rufus' support, to avoid being blackmailed ever again (Empire of the Son). Soon after, she is sentenced to house arrest (The Kids Stay in the Picture) and the two plan to live through the arrest together until she is released.
In The Jewel of Denial, Rufus excitedly tells Lily that he has worked out a deal for her to be released early. In Cross Rhodes, CeCe passes away and Rufus supports Lily. However, that same day, Charlie Rhodes is revealed to really be Ivy Dickens, a girl Lily's sister Carol Rhodes paid to play her daughter to get her trust fund. Soon after, it's revealed that CeCe left Ivy everything in her will; a fact that doesn't sit well with either Carol or Lily; especially after Ivy is given Lily's penthouse, as it technically belonged to CeCe (The Princess Dowry). Lily, Rufus, and William, who is the executor of the estate, are able to freeze CeCe's assets. Rufus works out a deal with Ivy for her to move out of the penthouse if Lily unfreezes the money. Lily hesitantly agrees to release the funds and Ivy moves out and goes to the bank. But when she arrives, she learns that Lily never unfroze the money and she was tricked. When Rufus finds out what Lily did, he begins to distance himself from her (It-Girl Interrupted).
In Despicable B, Lily plans to throw a family dinner and invite the media to dispel any bad press about herself or her relationship with Rufus. However, her plans are thrown when she learns that her real niece, Lola Rhodes, was fathered by William when he had an affair with Carol while they were married. Wanting to deal with the situation, she lies to Rufus that dinner was cancelled and arranges for Carol to be arrested. Rufus quickly figures out what happened and informs Lily that he thinks they need to take some time apart. In Raiders of the Lost Art, Chuck discovers that his father, Bart, is really alive and that he faked his death to avoid being murdered by a real estate competitor. He works with Serena, Blair, Nate, and Lola to bring him out of hiding, which they successfully do (The Fugitives). In the season finale The Return of the Ring, Rufus and Lily learn about Bart still being alive. Rufus learns that since Lily and Bart are technically still married, Lily needs to choose which marriage she wants to annul. Not wanting to lose her, he sends Bart annulment papers behind her back; which Bart signs. That night, Lily is shocked when Bart gives the signed papers to her and then she realizes what Rufus did. She informs him that it's her choice who she chooses to stay married to and rips the papers in half. Later on, she chooses to annul their marriage to save her relationship with Bart.
In the season premiere Gone Maybe Gone, Rufus enters into a relationship with Ivy. In Where the Vile Things Are, Rufus and Ivy plan to open their new art gallery but are shocked when they discover no one RSVPd to the event. They quickly figure out that Lily sabotaged the event and Ivy decides to use the money CeCe left her (that Lola gave back to her) to buy out Lily's event. Wanting to show them up, Lily plans to auction a piece of her own; but realizes she made a mistake when Bart tells her that that painting is where he hid the records of his illegal oil trade deals. She attempts to buy the painting back but fails, as Rufus won the auction.
In Save the Last Chance, it's revealed that Ivy is really dating William and only using Rufus to hurt Lily. When Rufus sees her hugging another man, he realizes he's being used and breaks up with her. Ivy moves out of the loft, but doesn't notice Rufus take the oil records from her. Not knowing that Rufus has the microfilms, she baits Bart and Chuck into trying to hurt Lily but quickly realizes she has no leverage and is in over her head. While that goes on, Rufus brings Lily the microfilms and apologizes for everything. They make amends and begin acting civilly again.
In the series finale New York, I Love You XOXO, it's revealed in the time jump that Rufus and Lily are friends again. Lily has reconciled with William and Rufus has begun dating Lisa Loeb. They greet each other at Dan and Serena's wedding and act friendly with one another.
Lily: Tell me something. Rufus.
Lily: Something you shouldn't.
Rufus: I never wanted to weigh in on your relationship with Bart. I was afraid of what I might say.
Lily: Which was?
Rufus: I let you go on your wedding day because... I was afraid I couldn't give you what you needed. I wasn't sure what I needed. And I have regretted it every day since.
-It's a Wonderful Lie (2x12)
Rufus: Love can fix things!
Lily: Oh, we both know that's not true.
Rufus (to Lily): You're scared because you're in love with me like you've never loved any of your husbands. And unlike a Bart Bass, someone like me can break your heart and that's terrifying. And I know that because right now you're breaking mine.
Lily (in her vows): Rufus, I know that our future will be just like us. Flawed and fragmented and full of more love than I ever thought possible. I am so excited for you to be my husband. And for our children, all of them, to be my family.
-Rufus Getting Married (3x05)
Rufus (on Dan, Olivia, and Jenny acting weird): I am sensing something else is going on here.
Lily: Well, you didn't actually think they wanted to play five hours worth of board games with us, did you?
-The Grandfather: Part II (3x08)
Rufus: If it helps you out, I'm totally free.
Lily: I had a feeling you might say that.
-The Debarted (3x12)
Lily: I didn't want to hurt anyone Rufus, I really thought I was helping-
Rufus: I'm sorry, Lily, but I don't know if I believe that anymore.
Lily: Can we please just.. stop fighting, and just pack and go home?
Rufus: I don't know, Lil. Right now, this loft feels a lot more like home than our apartment.
-It-Girl Interrupted (5x19)
Lily: Rufus, it seems I've made too much salad..... Fine, I had it delivered, but it's a generous serving, enough for two, and I just happened to find myself in this neighborhood and I thought maybe you might like some leftovers.
Rufus: ....You just happened to find yourself in this neighborhood?
Lily: ....I may have ordered a car, with no other destination in mind than this one. Please, take it.
Rufus: I will eat your refuge but we both know that's not why you're here. Why can't you just admit you wanted to see me?
Lily: Okay, fine. I missed you. I said it. Rufus, the Upper East Side holds all the comforts I desire - clean sidewalks, Bergdorf Goodman, and people whose job it is to open doors. But there is no you. And you're the only comfort I really need. The apartment just doesn't seem like a home without you in it.
-Salon of the Dead (5x20)
Lily (to Rufus): I can only have one marriage. And this just isn't one anymore.
-The Return of the Ring (5x24)
Rufus: Ivy can afford any painting she wants.
Lily: And with what money? I know it's not yours.
Rufus: You're right. It's CeCe's.
-Where the Vile Things Are (6x06)
Rufus (to Lily): After everything we've been through, I think it's safe to say we won't be together again but we were family for a long time and that means something. I'd really like peace between us.
-Save the Last Chance (6x07)