- Astor is dumped by Mila. He bumps into her ex friend, Cali. She shows him how to get Mila back/approach women and what he did wrong in the past.
- Astor's happy tenacity spoils his one chance at love with his lifelong crush Mila. Convinced he needs more experience with women to win her back, he engages her ex-best friend Cali to teach him how to woo women.—AGGK Films
- Astor (Fran Kranz), a zoology major, has dreamed of being with Mila (Beau Garrett) since childhood. One night, after drunken revelry on his birthday, he brings her home to care for her while Mila was vomiting all over the place. One thing leads to another, and a brief awkward courtship begins. Having idolized her for so long, and being an incurable romantic, the courtship ends as abruptly as it begins. Still obsessed with Mila, he turns to her close friend Cali (Dichen Lachman), who recently stopped speaking to Mila for reasons unknown. This leads him in unexpected directions. Cali begins to train Astor on how-to pick-up girls & how to be attractive to them as a mating partner. Cali teaches Astor to be confident, and not to put up an act. Cali says that Astor held out on teenage sex as he had a childhood crush on Mila. She argues that true love involves sex and not abstinence. Mila used to smoke and when they were 12 her dad almost caught her, and she put out her cigarette on Astor's chest.
Through the training we see flashbacks of how Astor was a sensitive, caring, sweet lover to Mila, & how Cali comments on each of Astor's & Mila's encounters as a major loss for Astor. Astor joined a cardiology course to help Mila study & even took the exams for her & scored her an 89, while his own scores dropped 10% due to his ignoring zoology. Astor is truly & deeply in love with Mila & utterly romantic. He writes romantic poems and uses lovely adjectives to describe the time he has spent with her, or how she is in bed. Mila is friends with a stud named Jake, who always tries to humiliate Astor in public and is a bit of a bully. Mila's friend Jenny (Miracle Laurie) is especially appreciative of Astor's romantic feelings for Mila. One day Astor overhears Mila telling Jenny that she wants a manly man (and that Astor doesn't even know how to unhook a bra). This is what brought Astor to Cali to learn the tricks of the trade of picking girls.
During pick-up training Astor meets a Roman Catholic girl, who has vowed to not have sex before marriage. Susie comes across as a bit of a dork and unattractive. During training Cali meets a Frenchman Frank (Karim Saleh), with whom she has a very passionate relationship, which ends when she finds him cheating on her. Cali teaches Astor all sorts of pickup lines, and even asks him to buy free drinks for the girls, but nothing works as Astor keeps striking out.
Astor has a better relationship with Cali. Astor takes Cali with him for bird-watching. At a bar Astor runs into Jake (Enver Gjokaj) and realizes that Jake is now dating Mila. Astor is angry at Mila that she has moved on so quickly and challenges Jake to a fight outside the bar. But they only end up bruising each other and going their own separate ways. Astor goes to parties with Cali but keeps striking out with the girls as none of his pickup lines work and he is really awkward at making small talk. When Astor gets into trouble, Cali is always there to help him out and even defends him in front of women who call Astor pathetic.
Astor goes to meet Mila to return her panties (he also asks Mila to make up with Cali) and is confronted by Jake. Jake has a heart attack, & Astor saves his life by taking him to the hospital. It is then revealed that Jake has premature ejaculation problems & Mila is deeply dis-satisfied with him.
Astor tries to bring Mila and Cali together. Cali is angry with Mila & Astor finds that it was because Cali invited Mila for a threesome with her boyfriend & Mila ended up taking over the relationship. Astor discovers that his new neighbor Divinity (Caitlin Stasey) is hot. But his interactions with the neighbor blow hot and cold as sometimes she does not even pretend to recognize Astor. One night she comes over Astor's place to have drinks & Astor is guided by Cali in his interactions with Divinity. Divinity almost has sex with Astor but finds his phone with all the texts from Cali goading Astor on. Astor finally figures out that Cali cares more for him than any other girl he has ever met & leaves Divinity to go meet Cali. But Cali tells Astor that he is a romantic, look for "the one", which she definitely is not.
Astor is heartbroken & returns to Divinity, only to realize that they are twin sisters actually named Trinity and Divinity. They proceed to have a threesome with Astor, when Mila shows up at his apartment & tells Astor that she really appreciates what Astor did for Jake & that she is breaking up with Jake. Mila then finds Trinity & Divinity & realizes that Astor has moved on. Mila tells Astor that she is offering him a second chance at a relationship & sleeping with the twins would mean they would no longer be friends.
Astor chooses Mila, a fact that deflates Cali. Astor realizes that he doesn't love Mila & breaks up with her. Mila tells him that it's obvious that Cali loves Astor. Astor broods over this for 3 weeks and finalizes realizes the truth behind the statement. He proposes to Cali & she accepts to be his girlfriend.
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