The film opens by introducing Andy Stitzer, portrayed by Steve Carell, a 40-year-old man living a remarkably organized life in a tidy downstairs apartment, filled with an impressive collection of action figures and video games. His high-tech gaming setup, complete with a video chair, reinforces the juvenile vibe of his space, despite his age. The day begins humorously as Andy faces a common morning struggle, only to transition into crafting a flawless breakfast omelet, accompanied by fruit and juice, showcasing his meticulous nature.
As Andy steps outside, he engages in casual conversation with his upstairs neighbors, making plans to watch Survivor. After this friendly exchange, he hops on his bike and heads to work at a large electronics store—akin to “Best Buy.” In his role in the inventory control room, he remains mostly hidden from the public eye, where his friendly demeanor clashes with his colleagues' perception of him as an eccentric, or perhaps a serial killer.
An unexpected twist occurs when Andy's coworkers realize they are short a player for their poker night and invite him along. To their shock, Andy impressively wins the game but falls into embarrassment when the conversation turns to sexual experiences. Struggling to fit in, he fabricates a story, which leads to the revelation of his virginity. This causes him to ride home in humiliation, considering quitting his job.
The following day, the workplace carries a tense atmosphere as colleagues start teasing him, prompting Andy to flee in embarrassment. However, one of his poker mates encourages him, rallying the rest to help him shed his virginity. The next stretch of the film displays a series of comedic attempts at matchmaking for Andy, ranging from hilarious parties to clumsy encounters, with the peak being a painful chest-waxing experience that leaves him bloodied yet resolute.
With various humiliations under his belt, Andy has a fateful encounter at work with Trish, played by Catherine Keener, who owns a quaint shop nearby, “We Sell Your Stuff On eBay.” This sparks a connection, and she freely shares her phone number with him, prompting excitement within Andy’s circle. However, they insist he must first lose his virginity elsewhere, fearing that his first time with Trish would be disastrous.
Despite numerous setups, nothing seems to work for him until he finally goes on a date with Trish. When it appears they might reach an intimate moment, a mishap occurs involving Trish's daughter and her boyfriend, leading to a comical mishap with numerous used condoms strewn across the bed. This hilarious yet awkward moment halts their plans, shifting their focus to getting to know each other better, leading to a sweet arrangement of waiting until their 20th date to explore physical intimacy.
Their relationship deepens, with Andy growing closer to Trish’s daughter and even receiving her support in realizing his ambition of owning an electronics store, showcased by her helping him sell items online. However, turmoil strikes when Trish discovers a stash of adult films that Andy received from friends, causing an emotional outburst that prompts a chaotic chase, culminating in Andy crashing his bike. In a heartfelt moment upon his confession of virginity, they embrace passionately.
Eventually, they find themselves at the altar on their wedding day, marking a significant turning point in their relationship. On their wedding night, they share their first intimate encounter, which is humorously brief; though she congratulates him with a quirky phrase, “congratulations, you are officially not a virgin.” After a few whimsical moments, the movie closes with a lighthearted scene featuring Andy singing “Aquarius,” surrounded by a vibrant montage of the ensemble cast.
