Chicago hairstylist Bastian Russo has only three things to his name: a pair of $1,200 shears, a Boystown studio apartment, and a list of men's names written on his closet wall. His constant worry that he's not good enough and his chronic inability to trust are what leaves him heartbroken time and again. After he adds the latest name, he turns to his best friend, Andres Wood, for solace. But instead of treating Bastian to dinner, drinks, and the usual effortless banter, Andres makes an interesting suggestion: that Bastian should get over the breakup by dating ... Andres. Sure, Andres is successful and attractive, but he also knows everything there is to know about Bastian—including what an insecure pain in the ass he is. Meanwhile, everyone in Bastian's life, from his mother to his co-workers, thinks he's an idiot for not having dated Andres already. So, what could go wrong? Everything. Now Bastian has to sort out his inadequacy and trust issues to prove he's worthy of transitioning from Andres' best friend to his lover. Otherwise, it's a matter of time before one or both of them end up on Bastian's list of Boystown Heartbreakers.