Kirk Kettner is an average, insecure airport security worker stuck in a dead-end job. Surrounded by friends who are equally directionless, his self-esteem takes a further hit when he realizes his former girlfriend has moved on. Everything changes when he accidentally meets Molly, an intelligent and stunning event planner, at the airport. When Molly leaves her phone behind, Kirk returns it and she expresses her gratitude by inviting him to a hockey game. To his astonishment, they hit it off and she shows genuine interest in him. Despite their chemistry, Kirk doubts that someone as extraordinary as Molly could truly be interested in someone as ordinary as him.

As Kirk gets increasingly nervous about their budding relationship, his insecurities are exacerbated by his skeptical friends and disapproving family. Their critical opinions and endless comparisons lead Kirk to constantly question his worthiness. Tensions rise as he faces one awkward situation after another, from meeting Molly's successful ex-boyfriend to dealing with his own ex-girlfriend who suddenly wants him back. Throughout these challenging interactions, Kirk struggles to gain confidence and believe that genuine affection can exist between the two of them despite their apparent differences. Eventually, the strain of self-doubt and external pressures prompts Kirk to reevaluate what he truly desires from life and whether he can overcome his fears to attain it.