In this world some people are losers, some people are winners, and some people get married to their best friend's ex-girlfriend/baby mama in order to win a bet the two of them made in high school. When Catalina returns from a 4 month long business trip and to find out that her best friend, Jayce, is getting married in less than two months, she does what any rational, mature, well meaning individual does: proposes marriage to her "straight" friend-with-benefits, Alyssa Levin, who she's been hooking up with ever since Alyssa and Jayce ended their disastrous relationship back in college. Catalina thought her plan was foolproof: she'd beat Jayce to the altar, get her mother off of her back about her being nearly 30 and unmarried, have someone to watch her apartment for her when she had to leave out of town for business, and have someone to bring her home food when they got off work...kind of like a live in maid that she got to sleep with, too. It turns out, however, that trying to have a meaningful marriage with a woman that you have great sexual chemistry with (but a crappy friendship), in order to win a bet, might not have been her smartest move ever. As she and her new wife struggle to find a way to live with each other, Catalina learns that the only thing worse than winning might just be losing.