Dating as a plus-size woman has been exhausting for Haleigh Berkshire. Sure, she's only twenty-five, but she's been doing it for a decade, and she's beginning to think it's time for a sabbatical. It doesn't help that she's been madly in love with her best friend, Jack, for years--but one disastrous weekend in college taught her the hard way that they'll never be more than friends. With her sister's engagement party fast approaching, and her friends and family nagging her about a plus-one, Haleigh and Jack do what they do best: scheme. Haleigh agrees to let her friends and family set her up with ten men or women--and she's sure that, once none of them prove to be good matches, her loved ones will finally let her fade into romantic retirement in peace. To her surprise, some of Haleigh’s dates go better than expected, and for the first time in forever, she's actually having fun. Until Jack starts breaking all the rules they’d made to mend their friendship in college. He produces a laundry list of flaws for everyone she likes, crashes some of her nights out, and finally shocks her by throwing himself into the mix. Dating Jack has always been the dream, but Haleigh is afraid of the reality. Is it worth risking her best friend for something that may have never been meant to be?