Mark moves in with his former crush, Katie, and her roommates, hoping she will fall for him. However, Mark doesn't make a great first impression with Hope, one of the roommates, who just happens to be Katie's best friend.

Katie goes to a tarot card reader where she learns that she has already met her future husband. Now that she has learned this piece of information, Mark tries to convince Katie that he is that man.

Hope persuades Mark and Thom into hiding her secret from Katie about her job.

Hope's father arrives unexpectedly and wants her to come home as he is unsatisfied with her job situation. Wishing to stay in New York, Hope makes believe that Mark is her boyfriend and that their love is enough reason to remain.

Katie sets Mark up on a blind date with Jenny, her former co-worker. Disaster ensues when Mark assumes that she is "hetero-flexible".

Katie begins dating a new guy in an attempt to move on from Ben: a mattress store owner who resembles Mark, yet possesses the confidence that Mark lacks.

Hope asks for Mark's help in finding a new job after she quits working at the coffeehouse. But Mark's boss would prefer a hookup, and he's more interested in Katie than Hope.

Katie passes off a business idea of her own which she had stolen from Hope, then lies about what she had done and pretends she got Hope a job.

Mark finally gets what he's been waiting for as the gang have a game night at the apartment.

Mark uses theater tickets to try and win over Katie after she and David return from their business trip.

The gang helps James' mom prepare for her first date since her divorce. But when things don't go well, she looks for comfort from Mark.

The evening does not go as expected when the roommates invite their ex's to attend a party with them. Katie still hasn't made up her mind between Mark or David.