My Awkward Sexual Adventure effectively lives up to its title, as it centers in on Jordan (Jonas Chernick), a conservative, overly-cautious accountant, who is dumped by his girlfriend Rachel (Sarah Manninen) as a response to his proposal of marriage. This comes the morning after she falls asleep while having "sex" with Jordan, and I abbreviate sex because it could've easily been mistaken for resuscitation. She advises that they do the good ol' "see other people" trick, where she can go out and have careless sex and orgies, while Jordan does, well, who cares? Jordan, who is heartbroken by her decision, wanders aimlessly throughout the cold streets, paying strippers and other local girls to pose for iPhone pictures with him to make his girlfriend green with envy. He gets bro-tips from his pal Dandak (Vik Sahay), who has been around the bend a few too many times, but gets truly vital help when he meets Julia (Emily Hampshire), a stripper who has a divine talent for culinary arts. When Jordan gets drunk out of his mind one night at the local gentlemen's club where Julia works, she graciously allows him to sleep on her couch as an act of courtesy and pity. Jordan informs her about his break-up, and Julia agrees to be his fellow "sex Yoda," who coach him through the ins and outs of meeting women and the tricky art of sex.
This is a hard film to do well and director Sean Garrity clearly knows what he's doing with the way he conducts the tricky, but promising topic of sex in older males. In a way, this feels like a work from Jon Kasdan, the man who recently directed The First Time. That film was a beautifully articulated coming of age drama about two teens who meet-cute in an alleyway during a party, and go on to have a weekend that will certainly be memorable for the both of them (do I need to say what their first time was). Both Kasdan and Garrity take a scalpel to the idea of sex, not glorifying it to be this simple thing that millions do everyday, but rather a frightening and intimidating experience for those unfamiliar with the required territory.
Sex is a tough subject and both pictures don't skate around that. They offer realism within their characters and intelligence with their writing. But one element that My Awkward Sexual Adventure triumphs over The First Time in is the level of awkwardness and anxiety brought to the screen. Seriously, I cringed more out of character sympathy during this film than any other film I've seen so far this year. The scenes where Jordan desperately tries to beg for Rachel's acceptance back into his life, the scenes where he resorts to photo-bombing with fellow women at a house party to make her jealous, the strange misconceptions he gets from Julia, and just his well-meaning nature that comes off as pure oddness forces you to be sympathetic towards his character.
Even though we have likable characters and a decently mature plot, that doesn't hide the film's inevitable dirty and problematic nature. Occasionally, the film does become too random at times. Consider a scene where a neighbor walks into Julia's condo and asks for a specific food, and the thing we're supposed to laugh at is the fact that he's pantsless and doesn't seem to care. Turns out, he never wears pants and implores Jordan to stare idly at his penis and proceeds to mock him when he refuses to stare for long enough. Randomness like that throws off what could've been an entirely sincere film from the get-go.
That and the problematic detour the third act takes when Rachel tries to enter Jordan's life again. The first two acts are carried by solid drama, efficiently articulated characters, quirky sexcapades that actually convey to film nicely, and a solid relationship between two unlikely friends. It's when Rachel tries to waltz back into Jordan's life that makes the film begin to falter. The film becomes so consumed with possibilities for them to argue, kiss and make up, argue again, run away, rejoice, etc that the overall speed increases from lax yet competent, to rushed and dizzying.
While My Awkward Sexual Adventure thoroughly lives up to its title, it doesn't use it as a simple cash-in for lame sex jokes. At times this film is so thoughtful and understanding to its characters problems and never drawing them as worthless punching-bags for comedy that one just wants to shake the hand of the director. At other times, one wants to remove the pen from writer Jonas Chernick's hand and tell him to take a short walk. This film is a roller-coast for atypical reasons.
Starring: Jonas Chernick, Emily Hampshire, Sarah Manninen, and Vik Sahay. Directed by: Sean Garrity.