stands Rufus up and accepts Bart's proposal ( School Lies). 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. 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. 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). During dinner, it comes out that Rufus and Lily used to date and Lily and Alison dislike each other for that reason.
When they arrive, Lily is shocked to discover Alison has returned. On Thanksgiving, Dan invites Serena, Eric, and Lily to the Humphrey dinner when he learns they have nowhere to go. They go together and they kiss, which leaves both unsure of their feelings for one another ( The Handmaiden's Tale). Later, she invites him to a party hosted by Eleanor Waldorf in order to make Bart jealous.
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). 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. In Pilot, Lily goes to see Rufus after she learns her daughter, Serena, is going on a date with his son, Dan. Lily and Rufus have no relationship in the Gossip Girl novels as Dan and Serena only date briefly and Lily is married to William van der Woodsen. 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. However, Lily later chooses Bart Bass over Rufus and annuls their marriage in The Return of the Ring. They begin dating again and eventually marry in Rufus Getting Married. They become friends again and realize they still harbor feelings for one another. The two began speaking again when they learn their children, Dan Humphrey and Serena van der Woodsen, have begun dating. She gave birth to a son, Scott Rosson, whom she gave up for adoption. Fearful of losing her money and mother, Lily left Rufus but discovered she was pregnant soon after. 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. Lily and Rufus originally met years before Pilot and had engaged in a serious romantic relationship while Rufus toured with his band, Lincoln Hawk.
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