Emma has been a thorn in Caleb's side since middle school. Having tarnished their friendship in eighth grade, she's now little more to him than an unkempt, unruly, disastrous bisexual mess. Over the years, she's gotten in the way of every romantic relationship he's attempted to settle into, using little more than mischievous charisma to lure them into her clutches.

To Emma, Caleb sets the record for World's Largest Stick in the Mud. Uptight, unbearably tidy, and a rule-follower, he's exactly the kind of boring person her mother wishes she was. When she discovers they're both after Juliet, the new girl, Emma proposes a competition to nudge him out of the way. Whoever can get Juliet to kiss them first wins, and the opposition must bow out with the promise of never talking to her again.

But plans go awry when Juliet seems mostly interested in hanging out with both of them together. Emma and Caleb just have to figure out whether winning Juliet's heart is worth the torment of constantly dealing with each other, andthe risk of reopening wounds from a past they thought they had left behind.