Several guests check into an upscale Manhattan hotel during the Christmas season. Diego Oliveros (Maurice Mejia) and Gabriela Santos (Catherine Toribio) check in with the intent on going to a winter formal. Diego has had flowers placed in their room hoping to impress Gabriela. Bob (Richard Herd) and Irene Burgess (Lee Meriwether) are a senior couple who unpack in anticipation of a stay for their 50th wedding anniversary. Bob suggests visiting a friend while they are in town, having forgotten the friend died two years ago. Rock musician Jack Livingston (Christopher Backus) facetimes with son from the road. He is in town to perform an alternative rock concert but promises his son to be home for two months once his New Year's Eve show in complete. Business conference attendee Susan Clark (Jaime Ray Newman) talks to her husband Kevin (Jonathan Kells Phillips) who call out of a sense of obligation without having much to say. Susan reminds him to take their daughters pageant practice. Jasmine Taylor (Jasika Nicole) and partner Katherine Taylor (Tracie Thoms) chose names for new baby but Jasmine prefers to keep the baby's sex a mystery. Diego struggles getting the cork out of a wine bottle before Gabriela comes out of the shower. Bob puts Irene's anniversary present in room safe and struggles to remember 1932 as the combination. Fellow conference attendee Ben Haney (Ross McCall) texts Susan with a dinner invitation but she declines, stating she is in for the night. Bob excitedly watches a fishing tournament on television. His wife Irene suggests he rent a boat and enter one of those tournaments, but Bob thinks the $400 to rent the boat for a day would be better spent on fixing the garage roof. Jack Armstrong gets a call from his agent Kate to do an eight-month tour as opening act for JRE. Bob and Irene try to take a selfie in their hotel room, but Irene is half cut out of the picture. Jack requests a night to think about the tour offer that his agent says provides the opportunity he has been waiting for. Courtney Chen waits in Presidential Suite until Sam Martin arrives. Courtney runs a company in the fashion industry she has taken over from her deceased father and is quite successful. Sam Martin is a painter who lives in the Village and struggles financially in the same way he did when he and Courtney were close. Susan talks to her daughter Madison who is excited to leave milk and cookies for Santa. Later, she questions Kevin about job interview which he has not followed up upon. Diego and Gabriela are dressed for formal. Diego is in military whites. Sensing Diego's romantic intent, Gabriela puts Diego in friend zone but teaches him to dance. Jasmine teases Katherine with her lack of underwear but them makes her finish her legal contract review that is due Monday for Katherine's employer. Later, they are headed to a party. Shannon sends a message to Jack that she going to miss his concert but suggests a late-night rendezvous. Susan texts Ben who is finishing dinner and invites him to come up to her room with a bottle of wine. Diego and Gabriela leave for the formal. Sam and Courtney eat dinner in her suite. They talk about Courtney's favorite painting that Sam created: a goat in sneakers. Ben brings Susan a bottle of Meiomi, her favorite brand of wine. She directs him that he is only there for wine and not sex. Bob has roses, champagne and gift from the vault waiting in the room for Irene. Courtney wants to have the conversation with Sam about what happened at the end of their relationship. Sam blames Courtney's father for her decision made about the baby she was carrying Bob and Irene dance in their room. Jasmine discovered at the party they attended about Katherine's hesitancy to have children. Katherine argues the couple should wait until she makes partner at her law firm and they have more resources. Jasmine wants to make a specific plan for them to start a family. Bob has framed a photo of he and Irene dancing on one of their first dates that he presents her as an anniversary present. In his conversation with Susan, Ben tells of his internal struggles of working for the corporation and throws out wild dreams of wanting to be Eddie van Halen even though he can't play guitar or start some kind of revolution that would be important. Susan claims to be happy but when Kevin calls, she sends it directly to voice mail. In addition to the framed picture, Bob has sold his Babe Ruth baseball card to pay for a trip through Europe for the couple. Jasmine says she is 35, wants two kids and argues the challenges of her biological clock to Katherine who wants to wait for at least a year before they start a family. Meanwhile, Irene presents Bob with two tickets to Les Miserable. Underneath the tickets is the key to a boat. At his concert, Jack sings a song he wrote for his dad who was also a traveling musician. Susan teases Ben about his OCD. He admits he has an apothecary in his home where he keeps his deodorants and flank oils. Courtney admits that neither she nor her father wanted a husband who could not support her. During that time, Courtney made efforts to get Sam a job as graphic artist, but Sam only cared about his art. Kevin calls Susan again. This time he is out of sleeping pills. Susan solves his problem by suggesting an a 24-hour pharmacy. Then she suggests to Ben they need a second bottle of wine. Gabriela and Diego return from the formal. Gabriela is upset that her ex, Jose, has been with Vanessa Vasquez. Gabriela says she only dates assholes and tells Diego she does not want to go to party but almost immediately changes her mind. Jasmine gives Katherine an ultimate: kids now or Jasmine will consider her options. Katherine thinks it best they part company given how she feels about ultimatums. Courtney confesses to Sam, the baby she was carrying was not Sam's. She claims she spent a single night with her ex, Peter after they had been drinking. Sam is devastated and leaves. Susan asks Ben what his MO is in seducing women. Ben claims he really doesn't have one and say he never bought a bottle of Meiomi for anyone before. Then Sam moves in to kiss Susan. Just as they begin, the phone ring interrupts them. Susan says she cannot continue the evening being that she is in such a weird place in life. Ben leaves before Susan fights with Kevin on the phone. She states she does not want to be his mother. Sam returns to Courtney's suite quite upset but with more questions. He says that they would have had a cleaner breakup if she had only told him the truth about the baby. Courtney reveals she would have kept the baby if it had been Sam's. Jack and Shannon relax in his room. Jack has owned and sold a large number of guitars over the years. Shannon compares guitars to the search for perfect man, stating that once you sell them, only then do you realize how perfect they were. Susan enters Ben's rooms with obvious intent. Courtney and Sam agree they have regrets about how their lack of focus on each other in their relationship. Diego and Gabriela return from the after party. Gabriela is intoxicated and offers herself to Diego. Diego says he will not have sex with her when she is in such a state. Bob snores but Irene's is awake and her mind is distracted as she looks at photo of their younger days. Jose texts to find out what room Gabriela is on. Gabriela has to throw up. In Ben's arms, Susan regrets being "that girl". Ben questions why she stays with Kevin. Susan justifies that she stays because of their daughter Maddy who is only six. Ben tells Susan of when his parents split when he was eleven and his father took him to a Dodger game. They were sitting close to a couple when a remembrance of the 1932 Olympics flashed on the video board. Ben said the couple hugged each other when the woman pronounced that they had been there. That is the kind of simple love Ben wants in his life. Sam and Courtney part company happy that they got through the conversation and put that difficult chapter of their lives behind them They promise not to take 10 years to see each other again. Gabriela throws up and regrets drinking so much. Courtney calls room service, ordering cake and a bottle of wine. Susan and Ben get into an argument. Ben will leave the job he abhors and Susan will not leave the marriage she is unhappy in. When Ben calls out Susan for playing the victim role, Susan dresses and leaves. Sam takes the wine and cake from the bellhop and delivers it to Courtney s suite. Katherine and Jasmine are not talking. Diego gets angry that Gabriela is like two different people. He believes Gabriela always sells herself short and ends up drinking too much and hanging out with guys like Jose. Sam and Courtney drink wine, play "Jingle Bells" on the piano and begin kissing. Back in her own room, Susan holds her head in her hands trying to make sense of the dynamic night. Jose (Josue Aguirre) shows up at Diego's Room and wants to see Gabriela. Diego tries to send him away. Gabriela appears and tells him off. She says to Jose that how Diego treated her and respected her is how she needs to be treated. Jose says she is not worth that and then threatens Diego before he leaves. Jack remembers a visit with his father which was brief as always, because his father always had to leave. Gabriela asks Diego if he really thinks she could go to college. Everyone sleeps, some more restlessly than others. The sun rises on a new day. Susan dresses for the conference. Diego wakes up with Gabriela in his bed. Jack does a phone interview with a disc jockey who is promoting Jack's concert that night. In writing his music, Jack says the words precede the tune. When the DJ asks what part of Jack's life that he likes the most, Jack is about to reply that he likes being on the road performing. He catches himself however and states that he really takes pleasure in is just being with his son. Jasmines tells Katherine a story of a girl named Erika Edwards that she knew in kindergarten. Katherine explains how happy she was when she held Erika's hand and how disapproving her father was. Katherine worries about bringing a child into world where so much pain is possible. But Jasmine assures her they are going to be such good parents that everybody will want two moms. Sam sketches Courtney while she sleeps. When Courtney opens her eyes, she says she looks terrible, but Sam thinks she will like her portrait. Diego brings Gabriela a bit of breakfast and bed and a small gift so she knows he will be back to see her at Christmas. Bob helps Irene with the clasp on her necklace. They both think they are lucky to have found each other. Jasmine and Katherine lay on the bed and discuss potential sperm donors among the men they know. Sam tells Courtney about his day ahead hanging Christmas lights for an elderly client who will try to seduce him. Susan comes to Ben's room to tell him she has resolved to leave Kevin. Susan doesn't want her daughter to think its normal to be in an unhealthy relationship. Ben says the previous night meant more to him than a conference hook up. Though his agent tries to convince him otherwise, Jack declines the tour opportunity to spend more time with his son. Ben calls Jason at work and declares he is handing in his two-week notice to leave his job. Diego and Gabriela look at photos from the previous night and grow closer. Just as they are about to part, Courtney spontaneously asks Sam if he wants to come to Paris. He leaves his Christmas lights job for the lights of Paris. They all crowd into an elevator on a ride down to the street level. Another group of strangers crowd into the elevator heading up to their rooms.