My Awkward Sexual Adventure (2012)

In the heart of Winnipeg resides Jordan Abrams, a 37-year-old accountant and quintessential pushover, who has harbored a burning affection for Rachel Stern since his boyhood. After years of lingering on the periphery of her life, he finally succeeds in making her his girlfriend. A year into their relationship, Jordan decides to express his lifelong devotion by proposing to Rachel during a romantic week-long vacation to Niagara Falls. However, his plan spirals into chaos when Rachel refuses to accompany him and breaks up with him, citing his lackluster performance in bed as the main reason. Unable to envision a future of mundane, unsatisfying sex, Rachel urges him to embark on the vacation alone, agreeing to discuss their break-up once he returns. Stranded in Toronto, Jordan finds solace in his college friend, Dandak, a man renowned for his sexual prowess. Dandak believes that the antidote to Jordan's heartbreak lies in diving back into the dating pool. However, Jordan is single-mindedly focused on winning Rachel back, thinking his best shot lies in improving his sexual skills under Dandak's tutelage and inciting jealousy by flaunting a sexy woman by his side. Enter Julia Bowe, an exotic dancer and Jordan's unlikely ally in his mission. She agrees to pose for a provocative photo and becomes Jordan's unconventional 'sex-education' teacher when Dandak's circumstances change. In return, Jordan assists Julia, who is financially inept, with managing her precarious finances. Their reciprocal relationship opens up a world of strip clubs, sensual massages, cross-dressing, and S & M to Jordan, helping him confront his sexual inhibitions. As they navigate the choppy waters of their unconventional student-teacher dynamic, deal with the aftermath of his trip and Rachel's absence, and as Dandak grapples with his new situation, they each inch closer to a profound realization about their desires and aspirations in life. The challenge lies in acknowledging these revelations and sharing them with the people who matter the most. "My Awkward Sexual Adventure" is an eccentric, humorous exploration of self-discovery, love, and sexual awakening.

My Awkward Sexual Adventure is a comedy movie featuring Jonas Chernick and directed by Sean Garrity.

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