A dorky, middle-aged man is pressured by his mother to settle down when he gets help from his eccentric friends as they resort to outlandish tactics in the pursuit of love as they navigate the intricacies of modern dating.

SYNOPSIS:

Johnny Grace, a dorky yet good-looking guy with confidence issues, cleans up by the dumpsters behind Hal’s Comic Book Store where he works. Johnny replays a voicemail from his overbearing mother, Ruth, who threatens to move in with him if he fails to find a nice girl he can settle down with. As he contemplates his dating failures and expresses his desire for a down-to-earth girl, his crass and manipulative best friend, Sacha “Tits” Lafferty, mocks him. Their banter is interrupted when Reese, a tomboyish and naturally beautiful woman who works at the bakery next door, appears and Johnny is instantly captivated by her presence. The pair have a history after once drunkenly made out, an encounter that meant a great deal more to Johnny than it did to Reese.

Johnny's nervousness leads to awkward small talk, while Tits constantly interjects with crude comments and innuendos. It becomes evident that both Johnny and Reese have experienced disappointments in their dating lives. Johnny musters up the courage to invite Reese on a date, fumbling over his words in the process. However, Reese politely declines as she’s too busy with work.

Reese returns to the bakery where her unfiltered and provocative friend, Brandy, berates her about her sexual dry spell. Brandy, acting as Reese's self-proclaimed cunnilingus guardian angel, encourages her to set aside her romanticism, lower her standards, and spice up her dating profile, highlighting her own promiscuous lifestyle. Reese, however, remains steadfast in her desire for a meaningful connection. Meanwhile, back at the comic bookstore, an encounter with Sebastian Davies, a British stoner, leads Johnny to reflect on his own romantic aspirations for a long-lasting relationship and he recognizes he needs to grow his confidence. To assist his friend, Tits emphasizes the importance of deception in attracting women and suggests Johnny follow in his footsteps by creating a strategically Photoshopped dating profile.

Tits and Brandy use their Photoshop skills to tailor-make dating profiles for their loveless friends. With his mother’s threat dangling over him, Johnny reluctantly permits Tits to embellish his profile with outlandish credentials, however, worries about his potential deception being exposed. Tits encourages Johnny to improvise if questioned about his experiences, suggesting he play it cool with clever responses, and forces Johnny to practice with him in a role-playing scenario.

Meanwhile, at the bakery, Brandy informs Reese that she’s arranged a date for her with her rich ex-boyfriend, Rex. Irritated, Reese agrees to the date. Johnny’s profile starts to get attention. He matches with Beth, a goth girl with a menacing profile photo, and they plan a date for that evening.

While Reese is getting ready for her date, Brandy advises she make her reserved outfit more provocative. Also out of his comfort zone, Johnny prepares for his date by applying gothic makeup and dressing in black with accessories to match his dating profile’s facade. Johnny waits in his car outside the trendy restaurant. When the clock strikes eight o’clock, he nervously hyperventilates and vomits on Reese's heels. Reese, initially mistaking him for a perv, kicks Johnny in the face. She apologizes when she recognizes him, and they share an intimate moment as she wipes blood off his nose. However, their conversation is interrupted by Reese's date, Rex, a muscular and confident dude. Johnny awkwardly interacts with Rex, who makes sarcastic comments and shows off his physique. Rex drags Reese away, and they say goodbye to Johnny. Alone again, Johnny checks his watch and nervously vomits.

Both Reese and Johnny go on to have devastatingly horrid dates. Reese walks out on Rex and Johnny is abandoned by his satanic date after his facade crumbles. At the end of the night, Johnny receives an enraged call from his mother who has been waiting at the airport for three hours. At the airport parking lot, while Johnny assists with his mom's bags, Ruth does not hold back from expressing her desire for Johnny to start a new chapter in his life and she’s come to make sure he does.