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Ally Darling (Anna Faris) is having breakfast with her boyfriend (Zachary Quinto), and she tells him that she wants him to take her to her sister’s wedding. He tells her he is not ready for that step and they break up.

Later at work, Ally is called into her boss’(Joel Mchale) office where she is informed that she has been laid off. While riding home on the subway, she reads a magazine article stating the average woman has 10.5 sexual partners in their lifetime. She scoffs at this, showing the article to another woman on the train who says it is ridiculous; the number is too high. Ally looks freaked out and starts making a list of all of the guys she has slept with. She comes up with the number 19.

Ally arrives at her sister’s pre-wedding party and gets drunk. She gives an inappropriate toast, basically insinuating that her sister’s fiancé was a douchebag, though he is okay now.

The scene turns into the bachelorette party at a bar, where Ally is sitting with her sister and the rest of the bridal party. She goes to the bar to get drinks and runs into her ex-boss. They flirt a little bit and then she returns to her group. She suggests a game where they all write down the number of sexual partners they have had, put them in a jar, and then each draws one and reads it aloud and they try to guess who each belongs to. As they start being read, everyone is in single digits, except for one girl who has had 12 partners. They mock her, calling her a slut, and Ally draws the last slip, her own, and rips it in half, so it reads 9 instead of 19. Her sister figures out the ruse and the girls rib Ally for having so many partners. They tell her that a study indicates that woman who have had over 20 partners never end up getting married. Ally says she is not worried, she still has one partner to go and that one will be the one she marries.

A montage shows that she ends up getting drunk and crazy at the bar and the next scene opens with her in bed with her ex-boss. She freaks out a little bit and calls her sister to tell her what happened. Her sister asks her if maybe this guy could be the one, and she starts to consider it. She then sees him get dressed, stick his hands down his pants and sniff his fingers, which helps her decide he is not the one. Someone knocks at the front door and she answers, letting in Colin (Chris Evans) who lives across the hall. He tells her he is locked out of his apartment and needs to use her phone. Meanwhile, her ex-boss starts asking her about going on a date. Colin, sensing Ally wants out of this situation, interjects that they have a tenant meeting that night. Ally tells her ex-boss she can’t go out, and he leaves. Ally thanks Colin for helping her out of the situation.

Ally and Colin chat a little bit. He asks about the sculptures she has around her apartment and she tells him that she is the artist. He tells her that his father was a police officer and so he is good at finding out things about people. She opens her door and sees a woman leaving Colin’s apartment. Colin confesses he was hiding out at Ally’s apartment, waiting for his latest conquest to wake up and leave. Ally scolds him, saying he is an affront to all woman and he leaves.

Analyzing her situation, Ally realizes if she sleeps with another man, he will be number 21, and she is doomed to be single. But, if she hooks up with any of her previous 19, she would be safe, so she decides to revisit her former boyfriends. She enlists Colin to help her find her ex-boyfriends, since as previously mentioned, he is good at researching people. In return, she allows him to use her apartment whenever he wants to hide from his conquests in the morning while waiting for them to leave.

Ally has lunch with her sister, which turns out to be a setup because her sister needs her help telling their mother(Blythe Danner) that their father(Ed Begley Jr.) is invited to the wedding. To divert her mother’s rage, Ally’s sister tells her that Ally and her boyfriend broke up. Their mother looks really disappointed, and we see that Ally has never been able to please her mother.

Colin informs Ally that he has had some success finding her ex-boyfriends, but he can’t make any headway with Jake Adams, her first boyfriend, whose father is a Donald Trump-like mogul.

Her first meeting is with a magician she used to date. She goes to see him at a bar, and is disappointed to find out he is still a bartender and still doing the same lame magic tricks. When Colin accuses her of snobbery, she says it is not that he is a bartender, but that he is in the same exact place he was years ago.

Next she meets up with a past boyfriend who is an Englishman. The scene reveals that the whole time Ally dated him in the past, she had pretended to be English, as well. Their reunion is short-lived as she is unable to maintain her English accent.

Next she flies to Miami to meet up with an ex who is now a gynecologist. He doesn’t seem to remember her until he starts examining her, which freaks her out.

Ally is getting to know Colin a little better, and she finds out he is a musician. He tells her that she should pursue her art, but she dismisses that suggestion as ridiculous. He jokes with her about wanting to sleep with her, but she always dismisses it, saying he is gross and treats women horribly.

Colin tells Ally he has found Tom Piper (Anthony Mackie) and that he is a senator’s aide in D.C. Ally “runs” into him and he invites her to a political dinner. He finds out she is staying in a cheap hotel and puts her up in a nice hotel and has a nice dress sent to her for the dinner. Ally is excited that she has found the one. The dinner goes really well, and Tom tells her that they make a great team and should get married. Ally says she’d like to make sure they have chemistry first, and Tom reveals that he is gay and wants her to be his beard.

Ally returns home dejected, and finds Colin in her apartment. He surprises her with some lit displays for her sculptures that he has set up to cheer her up. He takes her out for a walk, and they end up playing a game of strip basketball and go skinny dipping in the harbor. Colin offers to be her date to her sister’s wedding. They start making out in her bed, but Ally ends up telling him that she wants to slow down, so they end up just making out. The next morning, Colin suggests they hang out, but Ally has to go help her sister with wedding stuff. With her sister and her friends, she floats the idea of Colin as the one, and they all dismiss him, saying the way she has described him makes him seem like a guy you sleep with but don’t marry.

Ally returns to her apartment and picks up Colin’s phone by mistake and sees a text that indicates that he did find Jake Adams (her high school boyfriend) and didn’t tell her. She confronts him and tells him that he is a liar and that he is not the kind of guy she would marry.

Ally meets Jake Adams, and they seem to hit it off. When her mother finds out that Ally is with Jake, she approves of Ally for the first time.

As Ally leaves her apartment for her sister’s wedding, she runs into Colin who is dressed nicely. He says he is also going to a wedding. At the wedding, Ally dances with her father and he tells her that her mother never approves of her because she is so much like him. Ally starts to wonder if she is with Jake because it makes her mother happy. Ally gives toast in which she says that her sister knows she has found the right man because she can be herself with him. Ally realizes that she was always able to be herself with Colin.

She breaks up with Jake and heads out to find the wedding that Colin is at. It turns out his band is playing a ritzy wedding and Ally has to scale a brick wall to get into it. She goes onstage with his band and interrupts their performance. She tells Colin that she loves him, and they leave together.

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