Dating columnist Julia Allison makes a big move to Los Angeles on a quest to find Mr. Right. Matchmaking maven Amy Laurent has built an empire in New York City by bringing perfect matches together all thanks to "The Rules." But when an old flame comes back to town, she struggles to follow her own advice.
After her first date in Los Angeles fell flat, Julia hopes her luck will rebound on a date with a former college basketball player. Amy breaks another rule by dating the younger, albeit tall and handsome, Lewis. Meanwhile, Emily reluctantly goes on a date with one of her radio show guests, rapper Ray Luv.
Amy the matchmaker becomes Amy the client when she agrees to a blind date set up by a friend. Julia enlists a love coach to help erase her bad dating habits, while Emily visits her family in Michigan and goes out with her fifth-grade crush, David.
Emily interviews a polyamorous expert about open relationships and winds up with more than she bargained for. Julia visits a witch to help her move past her dating demons, but old habits die hard on a second date with a handsome man. Meanwhile, Amy breaks her rules and gives Lewis a piece of her mind.
Julia plans the night of her dreams and hopes her date, Andrew, is on board for the ride. Amy tries to be more laid back by dressing casually for her third date with Lewis, but is in for a surprise when the tables are turned. Then, Emily explores acrobatic yoga on a blind date, but is left wondering where the normal guys in San Francisco are.
After her co-host, Menace, sits her down for a heart-to-heart, Emily tends to old wounds in therapy. Amy tries to escape the breakup blues by visiting an old friend in Connecticut, but winds up with more drama than she can handle. Meanwhile, Julia is disappointed when Andrew can't make it to her dinner party, but is in store for a big surprise after dessert.
Emily's childhood crush, David, comes to town with a surprise in tow. Julia struggles with her dating column, as well as her new relationship with Andrew. Then, Amy breaks her rule against dating men she meets at the gym.
In the season finale, Amy must learn to be vulnerable in a new relationship, while Julia waives many of her checklist qualifications in order to date a cute math teacher. Then, Emily's highly-anticipated trip to Napa with David takes a sudden turn that changes their relationship forever.