Our film opens on graduation night, Walt and Roddy both having graduated that day, Walt from a journalism Master's program and Roddy from his 7-year Art History program (insert "it's where the chicks are" jokes here). Roddy has convinced a reluctant Walt to come with him to the big party that night, a thing Walt never does, being the quiet, bookish, stay-at-home, mild-mannered sort he is. But, since his girlfriend Jessica, another graduate, is busy with her girlfriends that night, and on account of the cajoling he's getting from Roddy in reference to his impending desertion of Roddy and this town for Jessica and the big city, Walt concedes.
The party is an affair of debauchery, a mixture of college kids, grad students and the like, all enjoying a well-deserved break. While Roddy is revealed to be a natural reveler, Walt is the obvious awkward wallflower, standing alone, avoiding conversation, all-around not enjoying himself. But out of the corner of his eye he sees a girl running playfully upstairs, Jessica, he thinks. He makes his way across the party and goes upstairs, finds himself in an empty hallway with several doors, all of them open but one at the end. He goes to it, hears a minor skirmish and a squeal from inside. Thinking Jessica in trouble, he opens the door. In the room he finds Jessica, topless, her breasts covered in chocolate syrup, and two eager young men, naked, ready to clean her. All are a bit shocked. What follows is a difficult, awkward, and chocolate-breasted break-up (that the naked dudes observe) in which Jessica says they've been together too long, since high school, and she'd been feeling cooped up for a while now, like she was letting her sexiest days pass her by. Until recently he was the only man she'd ever been with (was?!?), and she just can't continue to waste all this (chocolate breasts) on one guy. Walt counters that they're supposed to move to the city (any city) the next day. Yeah...she's not coming. Maybe later they can get together, settle into that grown-up life Walt seems so eager for, but for now, she's young, she's hot, her moral compass for the moment is out of whack and she wants to flaunt it. Walt, spineless, concedes and even leaves the room, closing the door behind him so Jessica and her new friends can get back to business.
Roddy spots Walt, dejected, leaving the party and follows him out, gets the story. Walt is freaking out, he's got a deposit on an apartment in the city, needs to start looking for jobs, but going alone freaks him out even more; he's ruined, his life is over. Roddy steps in and says he'll move with Walt, he's spontaneous and unattached like that. So it's settled.
We pick up with the two friends in the city where in the process of moving in Roddy meets a comely neighbor and disappears to sex her up, leaving Walt alone to move in by himself. When Roddy returns Walt confronts him about this, how it will be, Roddy with the ladies and Walt all alone, and Roddy assuages him by saying all they have to do is get Walt back in the game himself and it will all balance out; he's a free man for the first time as an adult, the first time ever, he should get out there and hump anything that will let him. To prove his point, Roddy takes Walt to a nearby bar that night, tries to help him meet women, but Walt is hopelessly awkward, doesn't know how to talk to women, certainly doesn't know how to pick them up. It's a disaster, in short, and Walt leaves embarrassed, ashamed and alone, while Roddy scores again. When Roddy returns later that night, he and Walt have a talk about the problem, how Walt can't communicate with women in the moment like that, his brain seizes up and he can't think of anything to say. If only there was a way to pick up women without having to look at them.
There is, Roddy declares, and grabs a laptop, directs Walt to a community message board that comes with a Casual Encounters section. Roddy explains the CE principle to Walt and why he thinks it's ideal: he's not looking for anything other than sex, he doesn't want to play games, and he doesn't want to talk face to face. He can communicate honestly and directly through writing, his strong suit. Walt doesn't know, he isn't sure, it sounds kind of, well, desperate and sketchy. It is sketchy and desperate, but so it the best sex, which Walt wouldn't know, having been with only one woman his whole life; he has to trust Roddy.
So trust he does, and allows Roddy to post an ad for him detailing what he wants in a sexual escapade. Walt has to get drunk as he does this, so nervous and timid he is, so it gets progressively lewder and thus funnier as he goes. Walt passes out before the ad is posted. Roddy finishes it for him by snapping a picture of Walt's package to post with the ad. As it turns out, Walt happens to be well-endowed, causing Roddy to curse all the time he spent writing when they could've just posted the pic.
When Walt wakes up in the morning, his inbox is flooded with willing women wanting to get down. Funny sequence going through the women, the pictures, the shapes, the sizes, the ages, the kinks, the personalities, all this, until he finds one that suits his purposes, someone, like him, that seems normal and even demure, bespectacled, quiet, just a mousy thing looking for a good time.
Now, from here we get into - pardon the pun - the meat of our movie, the encounters and how they effect him, so I don't want to give away much more than generalizations. What I can say is that the demure chick turns out to be the opposite, kinda dominatrix-y, the signs were all there in conversation but Walt didn't get it, and this rough but hilarious encounter freaks him out. Roddy convinces him to try again, promising this time to help him decipher the lingo via "micro-blu," an inner ear blu tooth device (a dash of Cyrano de Bergerac never hurt a comedy). This is where the vagaries in description begin.
Walt goes on another encounter, Roddy talks him through to the good stuff. Things get a little freaky, and when it's over Walt forgets he still has the blu tooth in, allowing Roddy to have heard everything, which disturbs him and disturbs Roddy as well for how much it turned him on, so both agree this plan was a one-time thing.
As Walt continues to navigate the strange world of no-strings sex he meets an array of characters: cougars, BBWs, curious lesbians, goth girls, good, old-fashioned trashy sluts, other kinksters, and among these one girl, different from him, fiercely independent, edgy, but cautious, who answers his ad a few times, but takes it slow, talking only the first encounter, standing close without touching the second, progressing like that, because her kink is the build-up. Walt is falling for her in a weird way, but she'll have nothing of it, because once they consummate, the build-up is over.
So as these aspects of our story wind around each other - the casual encounters eventually giving him the experience and confidence he needs to feel independent as a man and his burgeoning real affection for a girl he met that way - the monkeywrench of Jessica re-enters the picture. She's back, says she's been around and all she's found is that she had the best right where she was. She wants Walt back, wants to pick up where they left off, leaving Walt to make a difficult decision between his old, safe, static life and love or his new, exciting, dangerous and thrilling life, with it's possible new love (is there anything beyond the build-up? can it ever be more exciting?).
This one has it all: jokes, boobs, comic sex and a nice array of women characters sure to appeal to a broad range of men. Plus, I can't think of another sex-personals comedy off the top of my head, so it could be virgin territory, but without a single virgin. Would also work as a horror movie with minimal tweaks.
I'm just sayin'.