Genre: Romantic Comedy
Director: Nancy Meyers
Writer: Walter McKnight
Cast: Reese Witherspoon, Adam Scott, Cheryl Ladd, Chris O'Dowd, Anders Holm, Henry Golding, Lamorne Morris, John Michael Higgins
Plot: Kylie (Reese Witherspoon) lays in bed with the covers over her head. There is a knock at her door. Kylie puts a pillow over her head to try to drown out the knocks. Kylie's phone then begins to ring. Kylie declines the call. From out the hallway of Kylie's apartment, her mother Jacqueline (Cheryl Ladd) begins calling out for her to open the door already because she isn't going anywhere. Kylie begrudgingly gets out of bed and lets her mother in. Jacqueline looks around the apartment and is shocked by how messy it is and how little effort her daughter is putting toward being presentable. Kylie asks her mother what she wants. Jacqueline explains that she knows that Kylie has been depressed since her boyfriend left her. Kylie corrects her mother, saying her fiance left. Jacqueline says that she has been trying to figure out a way to help her get her life back to normal and has finally come up with something. Kylie asks her mother what he genius plan is, and Jacqueline tells her that she has signed her up to meet with New York City's number one matchmaker, Mr. Match, who will set her up with five eligible bachelors. Kylie tells her mother to cancel it, but Jacqueline tells her she can't cancel it because Mr. Match is going to be there any minute.
There is a knock on Kylie's door, and Jacqueline lets Mr. Match (John Michael Higgins) into the apartment. He immediately begins grilling Kylie with questions about herself while he snoops around her apartment. He asks her age and occupation and why she is single at this stage in her life. Kylie becomes defensive and refuses to answer his questions. Jacqueline tells Mr. Match that Kylie is 40 years old. Kylie glares at her mother. Jacqueline continues, stating that her daughter is a prominent magazine editor and she's single because her boyfriend left her. Mr. Match stares at Kylie for a long moment, before announcing that he has all he needs and leaves the apartment.
Kylie arrives at a fancy restaurant for her first date. She is seated at an empty table and awaits her date. Finally, Mike Smith (Anders Holm) arrives, wearing medical scrubs. He takes a seat across from Kylie when the waiter tells Mike that he is not dress-code compliant for the establishment. Mike loudly berates the waiter, informing them that he just got out of surgery where he saved the life of a child caught in the crossfire of a drive-by shooting and didn't want to be late for his date with the lovely Kylie. The waiter leaves, embarrassed. Kylie says that it's great that he was able to save the kid's life. Mike laughs and quietly tells her that he made that up so the waiter wouldn't hassle him anymore. He actually spilled some soup on his clothes at lunch and the only clothes he had at work were his scrubs. There was no kid, although he did perform a liver transplant, so that's something. Kylie is confused by Mike's story and asks him how long he's been a doctor. Mike sighs and tells her that he doesn't really want to talk shop, he just wants to get drunk and potentially get lucky. Kylie sips at her wine and looks at her watch. Mike proposes they get out of there and go back to her place, but Kylie declines. Mike shrugs and leaves the restaurant, taking his drink with him. Kylie calls her mother and complains about the date, calling Mike a tall scumbag.
For her second date, Kylie is supposed to meet the man at Central Park. She sits on a bench waiting, when Freddy Jenkins (Lamorne Morris) arrives, wearing an FBI windbreaker. He brusquely asks her if she's Kylie. She nods her head. He introduces himself as FBI Special Agent Freddy Jenkins, her date. She asks if he's on the job or something. He tells her that as an FBI special agent, he's always on the clock. As they walk through the park, Freddy eyes everyone they pass suspiciously. A man selling flowers comes up to them, and Freddy pushes Kylie away and demands to see the man's hands. The man drops his flowers and puts his hands in the air. Freddy demands to know what the man wants, and the man tells him that he was merely asking if he wanted to buy flowers for his date. Freddy asks Kylie if she wants flowers. Stunned by the situation, Kylie shakes her head no. Freddy orders the man to move along. Kylie's phone begins ringing. She looks at it and sees that it is her mother. She quickly answers the phone. Jacqueline asks how the date is going. Kylie pretends that there is an emergency and ends her date with Freddy early.
Kylie goes to Mr. Match's office and complains about the dates he has set her up on. He rejects her criticism, stating that he has set her up with a renowned surgeon and a successful FBI agent, so she should have nothing to complain about because he's doing his job - it's her job to go on the dates and be desirable. Mr. Match then tells Kylie that her next date should be a good one - it's with a famous chef who has his own TV show.
Kylie meets television chef Shane McNally (Chris O'Dowd) at a coffee shop for their date. Shane seems charming enough when they first meet, which is a relief to Kylie. Jacqueline then enters the coffee shop and pretends to be surprised to run into Kylie and her date. Kylie reminds her mother that she told her exactly where the date was going to be. Jacqueline claims she forgot and introduces herself to Shane, telling him that she's a huge fan of his show. Shane invites Jacqueline to join he and Kylie for coffee. Kylie glares at her mother hoping she'll leave, but she sits down at the table. Shane begins talking to Jacqueline, leaving Kylie out of the conversation and seemingly forgetting that he's on a date with her and not Jacqueline. Once they are all done with their coffee, Kylie asks her mother to leave so she can finish her date with Shane. Jacqueline agrees to leave, but Shane says that he actually has to get to the studio to shoot his show. When Shane is gone, Kylie yells at her mother in the coffee shop for ruining the first date she's had so far that was going well. Jacqueline apologizes to Kylie, saying she just couldn't help herself since she watches Shane's TV show all the time.
Kylie's next date is at the ice skating rink at the Rockefeller Center. She finds her date, Alex Newman (Adam Scott) waiting for her. He rents some skates for the both of them and get out on the ice. Kylie asks Alex to tell her a bit about himself. He explains that he is a middle school math teacher. He jokes that he knows that must sound super boring to her, but he loves teaching and he always had a knack for math so it is a pretty good fit for him. In front of them, a kid falls and is hurt. Alex quickly helps the kid off the ice to the kid's parents. After they are done ice skating, Alex offers to walk her home and she accepts his offer. While they are walking down the street, they run into Jacqueline and Shane walking hand in hand. Shane admits to the awkwardness of the situation, but tells Kylie that after meeting Jacqueline, he couldn't stop thinking about her. Kylie begrudgingly congratulates them and continues the walk home with Alex. When they arrive at her building, Alex kisses Kylie on the cheek and tells her that he would like to see her again.
Kylie meets her next date, male model Victor Chan (Henry Golding) at a trendy nightclub. Kylie feels very out of place amidst the loud music and dark lighting. Victor talks about himself and his modeling career the entire date, without ever asking Kylie about herself. A group of younger women approach Victor, having recognized him from a magazine. He gladly begins talking to them, asking them if they want an autograph or to take a selfie with him. Kylie takes the opportunity to slip out of the night club. When she is finally outside of the club, Kylie looks at her phone and finds that Alex has texted her a math joke: "I knew a mathematician who couldn’t afford lunch. He could binomials." Kylie laughs and calls Alex to see if he wants to meet her for a drink. He says that he has class in the morning so he probably shouldn't be hitting the town, however he was just cooking his "world famous chili" and invites her over to his place. Kylie agrees and he gives her his address.
When Kylie arrives at the building, she is surprised that a middle school teacher could live in such a nice, luxurious building. Alex comes down to the lobby to meet Kylie. They head up the elevator to his apartment, which is massive. Kylie asks Alex how he can afford such a nice place, and he explains that his family owns the building, as well as several other buildings in the neighborhood. He tells her how his family all works for the family business - a large New York City real estate company, but he never wanted to live in that world. He does say it's nice that his family charges him well below market value for rent though. Alex leads Kylie to the kitchen where the table is set up with two bowls of chili and a bottle of wine. Alex leans in to kiss Kylie. She happily kisses him back.
One Year Later:
A large wedding is underway. Kylie stands up at the altar, not as the bride, but as the maid of honor to her mother Jacqueline as she is getting married to Shane. After the wedding, Kylie and Alex are together on the dance floor. Alex then gets up on stage and borrows the microphone from the wedding singer and proposes to Kylie, who accepts as Jacqueline, Shane and the guests all clap.
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