Single divorce attorney Alex Turner is watching reality TV when she sees her latest ex's new fiancee picking out her wedding dress. Yet again, the guy she dumped went on to marry (or at least seriously commit to) the next person he dates after her. Fed up with being the precursor to happily ever after, she decides to interview all her exes to find out why-starting with her first boyfriend. Up-and-coming chef Will Harkness mixes with Alex like oil and vinegar, but forced proximity growing up means their lives are forever entwined. When Will learns Alex and her friends are going on a wild romp through Los Angeles to reconnect with her ex-boyfriends, he decides to tag along. If he can discover what her exes did wrong, he can make sure he doesn't make the same mistake with Alex. On this nonstop journey through the streets of LA, Alex realizes the answer to her question might be the man riding shotgun...