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Even though the movie starts out following the “hot girl nerdy guy” template, it ends up being more than that as revelations about school-focused hot chick Diane (Ione Skye) come out when she’s least expecting it, and no-future Lloyd turns out to be there for her.

One of the best films on this list (and Cameron Crowe’s directorial debut), it only ranks this low because Cusack’s “nerd” is the coolest thing about the picture. Can’t Buy Me Love (1987) Ronald Miller and Cindy Mancini A popular cheerleader (Amanda Peterson) pretends to be the girlfriend of a nerd (Patrick Dempsey) for a month in exchange for the

Even though the movie starts out following the “hot girl nerdy guy” template, it ends up being more than that as revelations about school-focused hot chick Diane (Ione Skye) come out when she’s least expecting it, and no-future Lloyd turns out to be there for her.One of the best films on this list (and Cameron Crowe’s directorial debut), it only ranks this low because Cusack’s “nerd” is the coolest thing about the picture. Can’t Buy Me Love (1987) Ronald Miller and Cindy Mancini A popular cheerleader (Amanda Peterson) pretends to be the girlfriend of a nerd (Patrick Dempsey) for a month in exchange for the $1,000 she needs to replace an outfit of her mother’s that she damaged.This movie also made a brief hit out of its title song, a Beatles classic, again. Superbad (2007) Seth and Jules, Evan and Becca OK, back to hardcore nerds.Since titling your flick after popular songs is still all the rage these days, can a movie called “Is She Really Going Out With Him? Overweight Seth (Jonah Hill) and his twitchy best friend Evan (Michael Cera) talk big shit, but they couldn’t get a girl if they tried.Albert Brooks is a talented reporter who, despite his not-so-hot looks and massive sweating problem, yearns to be on camera.He is secretly in love with his best friend and successful female producer and hot girl Holly Hunter, who doesn’t want to admit how attracted she is to the shallow but handsome anchorman played by William Hurt.

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Even though the movie starts out following the “hot girl nerdy guy” template, it ends up being more than that as revelations about school-focused hot chick Diane (Ione Skye) come out when she’s least expecting it, and no-future Lloyd turns out to be there for her.

One of the best films on this list (and Cameron Crowe’s directorial debut), it only ranks this low because Cusack’s “nerd” is the coolest thing about the picture. Can’t Buy Me Love (1987) Ronald Miller and Cindy Mancini A popular cheerleader (Amanda Peterson) pretends to be the girlfriend of a nerd (Patrick Dempsey) for a month in exchange for the $1,000 she needs to replace an outfit of her mother’s that she damaged.

,000 she needs to replace an outfit of her mother’s that she damaged.

With the release of the unimaginatively but appropriately titled “She’s Out of My League” last weekend—which despite the participation of “Undeclared” star Jay Baruchel doesn’t seem to have anything to do with Judd Apatow—yet another movie where the schlub gets the hot girl has entered the history books.Important note: Keep in mind that a wingman should never be too inexperienced or he will hold you back…the Wingman should always be of equal or greater knowledge then you.Learning and practiceing the Wingman support system is an unbelievable asset if done right.A ne’r-do-well dirty mutt named Tramp saves Lady from a group of street dogs and the two start an unlikely romance together. Fast Times at Ridgemont High (1982) Stacy Hamilton and Mark ‘Rat’ Ratner After getting tons of advice from popular hot girl and mentor Linda (played by Phoebe Cates), budding babe-in-training Stacy Hamilton (Jennifer Jason Leigh) goes the opposite way and starts falling for the usher at the mall movie theater, a mousy little nerd nicknamed ‘Rat’ (Brian Backer).Tramp, who scrounges day by day for food on the street, shows Lady the ropes of living footloose and collar-free and romances her with a dinner by candlelight that contains the film’s most iconic moment: The two each eat one end of a spaghetti noodle and eventually meet in the middle. Of course, she takes a minor detour into creep territory during one fateful afternoon in the pool-house with the school’s slick ticket broker Mike Damone (Robert Romanus), but that just serves to bring her closer to the thoughtful and sensitive Rat—even if he did put on Led Zeppelin in the car to try to ‘seduce’ her. There’s Something About Mary (1998) Mary and Ted, Healy, Tucker, and Woogie All of these movies—and romantic comedies in general, really—are about wish fulfillment.

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Wingman A Wingman is a guy you bring along with you on singles outings (like to bars) that helps you out with the women.

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