A Life of Routine

Andy Stitzer, a shy and introverted 40-year-old, worked as a stock supervisor at Smart Tech, an electronics store. His life remained structured and uneventful, centered around his collection of action figures and video games. Attempts at romance had been abandoned long ago after multiple failures, leaving him resigned to solitude.

One evening, a poker game with co-workers—David, Jay, and Cal—turned into a discussion about past romantic encounters. As the conversation unfolded, Andy’s lack of experience became apparent. His secret was revealed: he was still a virgin.

A Newfound Mission

News of Andy’s inexperience spread quickly at work, reaching even their boss, Paula. Embarrassed, he considered quitting his job, but David reassured him. Instead of running, David suggested another attempt at dating. Jay, Cal, and David took it upon themselves to help Andy succeed in romance, though their advice varied drastically.

David, hopeful for his own rekindled romance, invited Andy to a speed dating event. The experience proved fruitless for both, with David failing to reconnect with his ex-girlfriend, Amy. Meanwhile, Jay encouraged Andy to explore the social scene. Attempts included attending various events, enduring a painful chest-waxing appointment, and even a misguided encounter with a prostitute, all leading to embarrassment rather than success.

Cal, taking a different approach, advised Andy to shift the focus of conversations. Rather than talking about himself, he was encouraged to ask women questions. This strategy proved unexpectedly effective. A bookstore clerk named Beth found herself intrigued by Andy’s quiet curiosity.

In an effort to assist further, David provided Andy with his collection of adult films, urging him to gain confidence through experience.

A Promising Connection

A breakthrough came when Andy met Trish Piedmont, a customer at Smart Tech. Their first date ended in near intimacy, only to be interrupted by Trish’s teenage daughter, Marla. To Andy’s relief, Trish suggested they postpone sex, proposing a wait of twenty dates. He readily agreed.

Their relationship flourished over the following weeks. Trish encouraged Andy’s dream of starting a business, even supporting the idea by selling his valuable action figure collection. When Marla, seeking birth control, argued with Trish, Andy stepped in, accompanying her to a sexual health clinic. The visit resulted in Marla being ridiculed for her inexperience, prompting Andy to admit his own. His honesty earned Marla’s respect, deepening his bond with Trish’s family.

Personal Struggles and Growth

As Andy’s life improved, David’s took a downward turn. His lingering obsession with Amy led to an emotional outburst at work. He vowed celibacy, a decision that resulted in Paula assigning his sales responsibilities to Andy. As a result, Andy’s sales soared, earning him a promotion to floor manager.

Cal, hoping to help David move forward, hired a new employee, Bernadette, believing she could be the key to David’s recovery. Meanwhile, Jay faced his own relationship troubles when his infidelity led to a breakup with his girlfriend, Jill. Having realized the harm casual sex could cause, he admitted to Andy that physical relationships alone could not sustain romance. Following reconciliation with Jill, Jay invited Andy and their colleagues to celebrate her pregnancy at a nightclub.

A Night of Reckoning

On the night of their twentieth date, Trish attempted to initiate intimacy, but Andy hesitated. Confused and frustrated, she questioned his reluctance. The conversation escalated into an argument, and Andy stormed out, seeking distraction at the nightclub with his friends. Drunk and disoriented, he left with Beth, seemingly ready to move forward.

Elsewhere, Cal successfully paired David with Bernadette, and Marla convinced Trish to reconsider her reaction toward Andy.

Arriving at Beth’s apartment, Andy sobered up and realized he could not go through with it. Instead, he chose to leave. At that moment, his friends arrived, encouraging him to return to Trish.

A Long-Awaited Truth

Back at his apartment, Andy found Trish waiting for him. However, she had discovered David’s adult film collection and reacted with alarm, fearing she had misjudged him. Panicked, she fled.

Determined to explain, Andy chased after her on his bike. A miscalculated turn led him to collide with her car, sending him flying through a billboard truck. Rushing to his side, Trish listened as Andy finally confessed the truth—he was still a virgin.

Relief washed over her. Their love was affirmed, and the misunderstanding dissolved.

A New Beginning

Their journey culminated in a lavish wedding, funded by the sale of Andy’s action figure collection, which had generated approximately $500,000. That night, they consummated their relationship for the first time.

As their story concluded, the joy of their union was celebrated in an extravagant musical sequence, with all their friends singing and dancing to Aquarius/Let the Sunshine In.