NOTE: This spoiler was submitted by Jeremy

The film starts eight(ish) years ago. Lucy Gulliver (Geraldine Viswanathan) is lamenting to her best friends Amanda (Molly Gordon) and Nadine (Phillipa Soo) about breaking up with her boyfriend, who left her with a rubber ducky he won at a carnival on their last date. They go through a bunch of other keepsakes Lucy has from their relationship, and the other girls tease her playfully over it. The girls then decide to go hang out and take Lucy’s ex’s car since she kept his keys.

In the present day, Lucy lives with Amanda and Nadine, plus Amanda’s sort-of boyfriend Jeff (Nathan Dales). Lucy works at an art gallery for Eva Woolf (Bernadette Peters) and is dating Max Vora (Utkarsh Ambudkar). She tells her friends about how much she loves Max and how great she thinks he is. They later help her get ready for a gallery opening to showcase Max’s work.

Twelve hours later, Lucy is walking home drunk and crying. She gets into what she thinks is an Uber, but the driver, Nick (Dacre Montgomery), tells her that she is in the wrong car. Despite this, he takes pity on Lucy when she says that she had the worst night of her life. She recalls what happened – as she and Max were preparing for the opening, co-worker Harvard (Ego Nwodim) suggested to Lucy that Max is just using her to make him look good, which he even told her himself, but Lucy thought it was meant to be a compliment. Eva is very strict and demanding, which puts stress on Lucy. During the gallery, Lucy saw that an old friend of Max, Dr. Amelia Black (Tattiawna Jones), is there talking to him, and she felt threatened because Amelia is attractive. Lucy tries to announce Max’s work, but when she sees Amelia get too close to him, she goes off on a rant in front of everyone before falling down. Max told Lucy outside that Amelia is his ex, and that while he thinks Lucy is great, he wants to break up. To make things worse, Eva has fired Lucy. Nick sympathizes with Lucy’s story, just as she realizes that she got in the wrong car. She exits and tells Amanda and Nadine what happened, and they immediately console their friend.

Lucy spends three weeks depressed. Amanda and Nadine do what they can to get her out of bed and to cheer up, even trying to throw out stuff from her relationship with Max, but Lucy is hesitant to throw anything away. She later talks to another ex, Clayton (Raymond Ablack), who admits that he was very put off by some of the other keepsakes she had in her room. Lucy finds that she cannot even pawn off most of her items because most of it is useless garbage.

Later, Lucy goes to a restaurant (still carrying a trash bag of the keepsakes) where she sees Max and Amelia together. The hostess tries to hold her off, but she makes a run for it and nearly gets to Max until Nick, who is there with his friend Marcos (Arturo Castro), recognizes her and stops her from making an even bigger fool of herself. He takes her outside to cool off, but ends up getting in trouble when a nearby woman mistakenly believes he hit Lucy (she said he “manhandled” her), leading to the lady hitting Nick. Lucy walks away with him apologizing until he stops at a place he is sort of staying in. He says it is an old YMCA that he is turning into a building of his own that he calls “The Chloe Hotel”, meant to be modeled after the places he fell in love with after moving to New York. They sit to drink and talk for a bit before going through Lucy’s stuff. They find one of Max’s ties, which they hang up on a nearby canvas. It then gives Lucy an idea to create a whole gallery centered around belongings from other people collected from past relationships, which she names “The Broken Heart Gallery”. Throughout the film, characters are seen in videos explaining their belongings and why they kept them.

The next day, Nick goes to Lucy’s apartment. They go back to the gallery where he introduces her to Marcos, and Lucy offers to help with setting up the hotel in exchange for gallery space to set up. Nick is reluctant but agrees to help. Lucy puts the word out on social media to invite people to donate their exes’ junk. However, Nick is also having money issues, including some that he owes to Marcos, who is about to be a father. Lucy then goes around the city with Nick spending time, discussing feelings on relationships, collecting, and their personal lives and loved ones, such as Nick’s grandmother and Lucy’s mom.

While in a book shop, Lucy sees Max come in and buy something, but she tries to hide from him. When he leaves something behind, Lucy goes to return it to him and finds him meeting Amelia. They see Lucy and “catch up”, and before things get more awkward, Nick comes in to mention Lucy’s gallery and saying he is her assistant, which gets Max’s attention. They leave together, and Nick later takes Lucy to a sign that sells neon shops, and he also knows the owner. Nick gets a sign that says “in medias res” (“in the middle of things”).

At the hotel, Lucy finds one keepsake that is an unopened champagne bottle that the previous owner could not open after their fiance Dwayne passed away. The story even moves Nick and Marcos to tears. Word about the Broken Heart Gallery gets out on social media, with many of the donors spreading the word. Lucy later encounters a young woman (Suki Waterhouse) looking for Nick, but she declines to leave a message.

Lucy and Nick join their friends for Amanda’s birthday party. They perform a karaoke version of “Don’t Go Breakin’ My Heart”, where their friends can see their chemistry. Marcos encourages him to move on from his last relationship, but Nick doesn’t wanna talk about it. On their way home from the party, the girls find Max waiting for Lucy on the steps outside the building. After Amanda and Nadine tear into him, Nick shows up with cake for Lucy, nearly leading to an argument between the two guys until Lucy stops it and agrees to spend time with Max. Although she is still upset about him being with Amelia while they were together, he apologizes and begs her to give him another chance. He even took his tie from the hotel (it was unlocked) and insists that their love story isn’t over.

Nick tells Lucy that he was not able to secure a loan from the bank to be able to keep up with making the hotel, meaning that Lucy cannot hold the gallery there anymore. She tries to be optimistic, but he chooses to give up and tells Lucy to take her stuff. She still feels that she owes something to the people who donated their things for the gallery. Lucy spends the week trying to find other places that will let her host, but to no avail. Max suggests that she ask Eva, and although Lucy is nervous, she does so. Eva tells her she is a liability, but she comes around and agrees to let Lucy host the Broken Heart Gallery alongside Eva’s own work. After Max seems to take credit for helping Lucy, she asks Nadine for help in ending things for good with him. After a talk, she goes to Max’s apartment to do the deed.

Nick visits Lucy to apologize for being rude to her, and to tell her that he managed to score a loan to keep up the hotel. She wants to keep the exhibit at the hotel after the initial opening. With help from Amanda, Nadine, and Marcos, they all fix the place up to make it look neater. Lucy and Nick later acknowledge their feelings for each other and kiss before having sex.

While at a coffee shop, Lucy meets the barista (Chris Sandiford), who says that he is the one who donated the champagne bottle in memory of Dwayne. He tells her how the gallery has helped him find meaning and to move on, which touches her. She later goes by the hotel to try and find Nick, only to see him coming in with the woman who was looking for him earlier. She is his ex Chloe, whom the hotel is named after. Lucy is upset that Nick did not tell her about Chloe, and he admits that he was stuck on her for a while until recently. Lucy is still too upset and breaks up with Nick. He later goes by her apartment to try and apologize, explaining why Chloe was there, but Lucy does not appear to accept his apology.

Lucy is doing work at Eva’s museum, and Eva comes to speak to Lucy herself. She talks about her failed marriage, which she does not regret since it helped build her up into who she is now, but she adds that she also grew because she let go of it, and she encourages Lucy to do the same. Lucy goes home and finally throws away all of her exes’ stuff.

It is the evening of the gallery opening. Marcos and his wife Randy (Megan Ferguson) are set to go, but Nick pretends to be sick, even though Marcos knows he is just heartbroken. He then tells Nick that Lucy helped him get the loan since she managed to convince the lender to do so. He then goes off to take care of something.

Meanwhile, the gallery opens, with many displays set up to showcase past broken heart keepsakes and the reasons for being kept. As Lucy goes up to give a big speech, Nick comes in with a big neon heart sign that says the new name of the hotel, “The Broken Heart Hotel”. He professes his love to Lucy, and after the encouragement from the crowd, Lucy comes down to reciprocate her feelings, telling Nick she loves him too. They kiss, everybody cheers, and a dance party begins.

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Lucy Gulliver is dumped and fired from her job on the same night. She later meets a guy named Nick, who has a building that he plans to turn into a hotel. Lucy then gets an idea to start an art gallery for people who have kept belongings from past relationships, "The Broken Heart Gallery", as she has numerous items for exes that she keeps at home.

Lucy and Nick help each other build up the hotel and set up the gallery while falling for each other. Although her ex Max tries to step back into the picture, Lucy puts an end to it and pursues something with Nick. However, Nick's ex Chloe also comes in, and since he named the hotel after her, Lucy gets upset and breaks up with Nick.

Lucy opens the gallery at her former workplace after convincing her old boss to let her do so. Nick goes with a neon sign for the hotel, renaming it "The Broken Heart Hotel" in honor of Lucy, and he apologizes for not being forward with her about Chloe, among other things. The two profess their love for each other and dance with their friends in the gallery.