L'amore difficile

A group of people who were the inspiration of an author's fact-based, best-selling book are invited to a party at a mansion in the Hollywood hills to celebrate the making of the book into a movie which a series of situations, and bed-hopping begins between all persons involved.

Created by gay directors and actors, Boys On Film features numerous award-winning shorts that deal with all aspects of gay life. Volume 2: In Too Deep contains nine complete films: Till Kleinert's "Cowboy" starring Oliver Scherz and Pit Bukowski; Håkon Liu's "Lucky Blue" starring Tobias Bengtsson and Tom Lofterud; Matthieu Salmon's "Weekend In The Countryside" starring Théo Frilet, Pierre Moure, and Jean-Claude Dumas; Soman Chainani's "Kali Ma" starring Kamini Khanna, Brendan Bradley, and Manish Dayal; Julián Hernández's "Bramadero" starring Cristhian Rodríguez and Sergio Almazán; Craig Boreham's "Love Bite" starring Will Field and Aidan Calabria; "The Island" featuring director Trevor Anderson ; Arthur Halpern's "Futures (and Derivatives)" starring Kelly Miller, Cam Kornman, and Bill Barnett; and Tim Hunter's "Working It Out" starring Simon Kearney, Paul Ross, and Glaston Toft.

Flo is not quite a normal teenager: While all his friends only think about sex he can't even pronounce the word "S - E - X". But everything changes completely when one morning Flo wakes up from a strange call. His penis, excited for the first time, begins to talk to him. He claims that Flo severely neglected him for 15 years and it's time to release him.

Sasha tries to get her soon-to-be ex husband Kyle laid so she can move on with her sex life guilt-free.

Charlie (Curro), a 16 year-old boy, who apparently seeks to stop being a virgin. But he has fallen madly in love with a prostitute ten years older than he. It is difficult for him to approach her, so he decides to pay her for the services and in this way try to fall in love

The klutzy yet stunning Rebecca Sommers walks in on her hunky boyfriend in bed with another woman. They break up and Rebecca starts to fall apart, but, with the help of her close girlfriends, she begins to date again. Unfortunately, the men she meets all happen to be crazy. John, her dorky guy friend, tries to express his secret love for Rebecca, but she's too busy to notice as she tries to come to terms with her breakup.

At popular South Beach University, filthy rich super-snob Victoria English is the absolute queen of leading Greek student club, Sigma Sigma. In order to achieve her crowning ambition, winning FHM Magazine's annual best sorority, she must recruit atypical 'Sigmies' to fulfill the diversity criteria. Ambitious sycophant pledge Kristen Haas helps her attract 'losers' (too poor, ugly, unfashionable), who are cruelly put through excruciating hazing, without intent to actually enroll them. Gloria, the brightest and most assertive pledge, wins the heart of Derek 'baby Dick', Victoria's ideal, yet constantly abused boyfriend, whose bitch-addiction is cured by this alternative lover. Together they lead the revolt of the not-even-nerds.

Van Wilder has been attending college for far too many years and is scared to graduate, but Van’s father eventually realizes what is going on. When he stops paying his son's tuition fees, Van must come up with the money if he wants to stay in college, so he and his friends come up with a great fund-raising idea – throwing parties. However, when the college magazine finds out and reporter, Gwen is sent to do a story on Van Wilder, things get a little complicated.

Alex Fortini, a transplant to Milan, lives behind his lover who owns an advertising agency. When his wife, who had left five years ago, reappears, fearing that she will want to ask him for a divorce and alimony, he unwittingly gets into a lot of trouble.

When Spence and Hogan graduate from college, life is bleak. They have to work for heinous divorce lawyers that torture them. Spence has a girlfriend from hell and Hogan just wants to start his life already. As luck would have it, our two young men are presented with an opportunity, they develop a club of young men devoted to the older woman, the "Cougar" if you will.

After getting dumped by his slutty girlfriend, Caleb falls in love with Gwen. However, thanks to Caleb's roommate, Gwen thinks he's gay and sets him up with her roommate, Marc.