How to Be Single is a 2016 American romantic comedy film.
Synopsis[]
A group of young adults navigate love and relationships in New York City.
Plot[]
Alice temporarily dumps her college boyfriend Josh and moves to New York City to be a paralegal. She moves in with her sister, Meg, an OB/GYN who refuses to have a baby or any form of relationship. Alice befriends wild co-worker Robin, who enjoys partying and one-night stands, and local bartender Tom Wade who willfully embraces the bachelor lifestyle and hooks up with various women including Alice. Tom meets Lucy at his bar when she uses his Internet for free. She explains she is looking for "The One" using various dating sites.
Alice meets with Josh to tell him she is finished with their break and ready to get back together. Josh explains that they cannot because he is seeing someone else and rejects her bluntly, which distresses Alice. Meanwhile, Meg has a change of heart and decides to have a child via sperm donor.
Shortly after learning she is pregnant, Meg unexpectedly hooks up with a younger man, Ken (Jake Lacy), after meeting him at Alice's office Christmas Party. Ken who is the law office receptionist, is smitten with her. She repeatedly tries to break it off, but he continues to cutely pursue her. Thinking Ken is too young for her to have a future with, she hides the pregnancy from him.
Back at Tom's bar, Lucy has a string of bad dates. Tom witnesses this and realizes he has feelings for Lucy. As her sister kindles her own relationship, Alice continues to pine after Josh. In an attempt to put herself out there, she attends a Wesleyan alumni networking event, where she hits it off with a man named David (Damon Wayans, Jr.).
Lucy, having been in a relationship for three weeks with a man named Paul, goes to Grand Central Station to send him off to the train. Paul reveals that he has been seeing other people, thinking she was doing the same, and breaks up with her. Lucy, extremely agitated, breaks down at her volunteer job reading stories to children. George (Jason Mantzoukas), who works at the bookstore, soothes her and the two begin a relationship.
Alice and Robin attend Josh's winter holiday party, however Alice finds she cannot watch Josh with his new girlfriend. Walking alone, she runs into David, who shows her a private view of the Rockefeller Christmas tree. Dazzled, Alice thanks him and they begin a relationship. Three months later, as she is singing, "Can't Take My Eyes Off You", with David's daughter, Phoebe, David becomes upset with Alice, reminding her sternly that she's not Phoebe's mother; as it's revealed that David's wife died two years ago and he has not told Phoebe about it, believing that his daughter is not ready to know, which causes the two to break up.
On St. Patrick's Day, Alice bumps into Josh and his parents, and he appears pleasantly surprised to see her. Lucy comes to Tom's bar and shows him the swanky outfit she got for herself to share with George, whom she introduces to Tom. Tom becomes visibly upset, and he invites Alice to get drunk. The two talk about their frustrations with their feelings for Josh and Lucy, and end up sleeping together in an attempt to distract themselves. Meanwhile, Ken discovers Meg is pregnant, but is eager to help raise her child. Meg, concerned to believe that he is not truly committed, ends the relationship, with Ken walking away.
Later, at Alice's birthday party, Robin has invited Tom, David, and Josh without Alice's knowledge, only because she thought it would be funny. Shaken by the presence of all three men, Alice argues with Robin. Tom goes to confess his feelings to Lucy, who announces she is engaged to George. Then George threatens Tom to stay away from Lucy. Now sitting on the fire escape, Alice is joined by Josh. The two make out passionately, but stop when Alice is horrified to learn that Josh is now engaged and was simply looking for closure. Invigorated by a desire to find herself, Alice leaves to go home. Her cab hits Robin, who has purposely jumped on the windshield to get a cab for Meg, who is in labor. Alice and Meg rush to the hospital, where Meg successfully delivers a baby girl, naming her Madeline. Ken appears and convinces her to re-enter the relationship, while Alice repairs her relationship with Robin, who is revealed to be wealthy, living in an entire floor apartment.
The film closes as Alice reflects on her time living alone and being single. Tom is seen repairing his tap water plumbing, which he had purposely cut in an attempt to prevent hungover women from hanging around his apartment. Meg and Ken are playing with Madeline, and Robin carries on partying. Lucy has finally settled down with George. David finally tells his daughter the truth about her mother's death. And finally, Alice is seen hiking the Grand Canyon by herself so that she can witness the sunrise on New Year's Day, a dream she always had.
== Cast ==