Plot

Molly owns a quaint little sweet shop. Joel works for a gigantic candy company threatening to shut her down. How they meet, fall in love, break up and get back together is hilariously recounted in this rom-com spoof.

In New York City, couple Joel and Molly are having dinner with their couple friends, Kyle and Karen. In the general discussion of their respective relationships and how they met, Joel and Molly, in telling their story, say that it is exactly like a corny romantic comedy. The story they end up telling not only has every romantic comedy cliché thrown in, but it is told in the style of a romantic comedy, complete with crazy characters who should be smarter to figure out a smoother path to a happy ending for Joel and Molly. But that one romantic comedy element that is the big payoff may not be reality, or perhaps it is.—Huggo

Molly (Poehler) is a small sweet shop owner in New York City who is at risk of losing her business to a big corporation. Tasked with forcing Molly's eviction is corporate executive, Joel (Paul Rudd), who finds it difficult to put pressure on her because the two have fallen in love.

As Joel and Molly have dinner with unhappy couple Kyle (Bill Hader) and Karen (Ellie Kemper), they recount how they first began dating in NYC.

When Joel (Paul Rudd) and Molly (Amy Poehler) first met, it was hate at first sight. Joel's big Corporate Candy Company (CSR or Candy Research and Systems) threatens to shut down Molly's quirky indie candy shop. Joel considered himself to be a nice guy with a great job. Molly has just gone through a breakup with boyfriend Frank and is very clunky and prone to minor accidents throughout the day.

Joel is with Tiffany Amber Thigpen (Cobie Smulders), who is sexy hot and works in the fashion industry but doesn't reciprocate Joel's feelings quite the same way. Bob (Jason Mantzoukas), Joel's best friend and his coworker at CSR. Melanie (Noureen DeWulf) is Joel's secretary.

Trevor (Michael Ian Black) is Joel's rival at work who is looking for every mistake made by Joel on his accounts, so he can make him look bad in front of the boss. Trevor is stealing accounts from Joel and vying for the same promotion. It is implied that Trevor is having sex with Tiffany. Roland (Christopher Meloni) is Joel's boss and is a difficult person to impress.

When Molly finds that CSR is building a new super store across the street to her little shop (Upper Sweet Side), she visits her accountant Eggbert Flaps (Ed Helms) who tells her that her business has 6 months to live. When Joel is about to propose, he finds Tiffany having sex with Trevor. She admits to having an affair with Trevor for over a year now. Tiffany moves out and Joel invites his brother Jake (Max Greenfield) to live with him for a few days. Jake is a bum, who pretends to be the CEO of the Bacon Boot company, the fastest growing edible boot company in the entire country.

Bob is married to Brenda (Melanie Lynskey), who is best friends with Molly. So, Bob and Brenda invite Molly & Joel to a Halloween costume party. They bump into each other in identical costumes and start fighting until Bob and Brenda introduce them. Molly is angry to find that Joel works for CSR, and although she finds him very cute, she sees no future in their relationship.

Joel and Molly then run into each other at the local used bookstore and realize that they have very similar tastes. Molly thinks that she judged Joel too harshly earlier and asks him out for coffee. They bond even more over coffee and find even more things about each other and love each other's mannerisms. Molly then invites Joel over for dinner. Joel shares his dream with Molly of opening a coffee shop called "A cup of Joel.

Molly invites Joel for dinner. Thats when Joel realizes that Molly has a son named Tucker. Joel and Molly's son quickly befriend each other. But Joel can't kiss Molly as she reminds him of Tiffany. Molly is angry with Joel about that. Joel talks to Jake and realizes that life is too short.

Joel goes to the sweet shop to apologize, but both take so long getting ready, him rehearsing out front and Molly going through a montage of trying on outfits, that they miss each other. He eventually says sorry over the phone, and they begin dating. Molly invites Joel to her apartment, and they have sex.

Following a video montage of the couple laughing and enjoying themselves in piles of leaves, the greengrocer's etc, they do a road trip so Joel can meet her parents.

Molly takes Joel to meet her parents, who Joel realizes are white supremacists. Joel is angry and argues with Molly, but calls her Tiffany. Molly is furious & kicks him out. Joel goes back to his place and finds Tiffany there, broken up with Trevor and horny. They have sex.

Molly finds out and is heartbroken. She starts dating Eggbert. As Molly and Joel share friends, they coincide at the usual autumn festivities. At Thanksgiving Bob and Brenda invite Molly and Joel, who come with Eggbert and Tiffany respectively.

By new year eve, Eggbert proposes to Molly, and she accepts. Joel figures out that Tiffany is just using Joel and breaks up with her. He speaks to his grandmother, who makes him realize that Molly is the right girl for her.

Joel makes an impassioned plea to Roland to leave Molly's store open and to not destroy it. Roland agrees and gives Joel his big promotion. Joel declines and resigns stating his ambition to open his own coffee shop. Joel then finds out that Molly is getting married in 20 mins. He rushes to the wedding venue, only to find that Molly dumped Eggbert at the altar and ran away as "he wasn't the one".

So he goes to the Brooklyn Promenade to find her. All of the wedding guests follow Joel there. After Joel makes a speech declaring his love, after several interruptions, they agree to get back together. Thats when Spike (Molly's ex-husband and the father of her child) (Michael Shannon) reaches the spot and picks a fight with Joel for trying to steal his family. Spike has just been released from prison attacks him with a sword. Joel beats Spike and Spike is again apprehended by the police (only to suddenly be executed on site). Molly agrees to give Joel a second chance and they get married at the same spot exactly one year later. Joel unveils a folding coffee table now placed outside Upper Sweet Side, which he calls Cup of Joel.

But pretty quickly Molly's store shuts down, as the business goes to CSR anyways. Joel's "Cup of Joel" idea never takes off. Because of its Molly got addicted to pills and started sleeping with an old boyfriend (Frank) again. Molly's son begins to hate Joel and soon Molly and Joel file for divorce and become good friends.

After they finish telling their story to Kyle and Karen, both couples wonder and then agree to give their marriages another shot.