Sherman 'Tank' Turner, played by Dane Cook, is more than just a help line operator; he’s a notorious ladies' man with a peculiar side business. Whenever someone is heartbroken and wishes to win their ex back, they turn to Tank, who arranges for them to take their ex-girlfriends on intentionally dreadful dates. This strategy often leads the ladies to realize how good they had it with their previous partners. Tank’s antics mostly revolve around being exceptionally foolish—ranging from disastrous driving and terrible restaurant choices to outrageous lies, making sure that by the evening's end, the girls find themselves longing for their exes once again.
Living with him is his step-cousin Dustin, portrayed by Jason Biggs, who is infatuated with his coworker Alexis, played by Kate Hudson. Although they’ve been dating for five weeks, Dustin's heartfelt confession of love does not win her over, as Alexis insists on maintaining a platonic friendship while she prepares for a marathon. Feeling uncertain about his own love life, Dustin confides in Tank, who eagerly offers to help his friend win Alexis over, despite initially facing resistance from Dustin, who fears Tank's influence.
As events unfold, Tank finds himself joining Alexis on her marathon training runs, ultimately taking her out on a night filled with outrageous escapades. Though Tank’s behavior is its usual cringe-worthy self—he even suggests they have sex on the first date—Alexis, caught up in the moment and a bit tipsy, doesn't mind. However, once reality strikes, Alexis decides it's time for a change and starts seeing other guys, prompting Dustin to once again seek Tank’s help to sabotage her new flings.
Their romantic triangle takes a turn as Dustin's jealousy boils over amid a series of embarrassing attempts to keep Alexis close. Meanwhile, Tank’s feelings for her deepen, prompting a confrontation with his father, Professor William Turner, whose flippant views on relationships leave Tank questioning his worthiness of Alexis’s affection. After some misguided encounters, including a rotten date with an overly zealous Christian girl, Tank musters up the courage to genuinely pursue Alexis, leading him to a disastrous wedding where his past mistakes come back to haunt him.
The culmination of their chaotic journey comes with misunderstandings, revelations, and a battle of wits that sees both Tank and Alexis grappling with their feelings. Ultimately, after a series of emotionally charged confrontations and reconciliations, the film concludes on a hopeful note as it teases the rekindling of Tank and Alexis’s relationship. The film rolls credits suggesting a surprising match between Dustin and Alexis's roommate, adding a hint of future romance amidst the humorous turmoil.
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