Lillian Prescott has sworn off dating A mother to two beautiful children and the CEO of her own company, she's got more than enough on her plate. After running away to London at the end of her senior year, she's back home in Boston to introduce her children to the city where she grew up and to reconnect with her loving family. At a family event, she runs into Nate Gardner, her childhood best friend and the man she shared a passionate one-night stand with four years ago. Nathaniel Gardner loves sex He loves cultivating his playboy reputation, spending every night with a different woman, supplying the local gossip magazines with fodder, and driving his mother up the wall. Sick of the same monotonous routine of shuffling between work and home, he hopes to regain the joie de vivre of his early 20s. While attending a family friend's event, he bumps into the one woman he could never seem to forget, it's been four years since she left him naked and alone in a Madrid hotel room without a word as to why. And, he's determined to find out what exactly happened that night even if it means that she'll never talk to him again. Now, forced to work together to plan the biggest event the city has seen, they might have to reopen some old wounds and face some tough questions. Follow these two as they deal with scheming mothers, meddling best friends, and some of the cutest misbehaved kids you'll ever meet, all while trying to figure out what keeps pulling them together time and time again.