Gabi and Josh attend a speed dating event at the diner, and make a bet as to who can get the most dates. But in order to do so, Josh can’t reveal he’s wealthy, and Gabi can’t reveal what she really looks like. Not trusting each other to stick to the rules, Gabi and Josh end up on an awkward double date. Elliot tries to bond with Keisha, and looks to Yolanda and Sofia for ideas.

Gabi, Sofia, and Yolanda have to stay over with Josh while their building is treated for termites. But Josh and Gabi are uncomfortable staying together and try to make sense of an awkward situation. Meanwhile, Alan suggests a weekend getaway to cheer up Elliot, but his destination of choice is Josh's penthouse, making it an even more crowded house.

Broken hearted over Josh, Gabi ends up on someone else’s honeymoon.

Having recently discovered her passion for writing, Sofia is thrilled when she gets a chance to work for intimidating media entrepreneur Logan Rawlings, with Gabi supporting her all the way. However, Logan is as demanding as ever, and after a rocky start on the job, she gives Sofia one chance to prove herself – by landing an exclusive interview with a hot new artist. At a loss for what to do, Sofia turns to her new coworkers, intellectual Leo, who’s immediately taken with Sofia, and charming Kendrick, who’s caught Sofia’s eye. Determined to succeed, Sofia sets out to show Logan, and herself, that she has what it takes.

Josh is about to launch a new app and hires a new assistant Randall, who is the epitome of efficiency and work ethic, to help him with this busy time. Thinking Randall is a little too good at his job and out to get theirs, Gabi, Elliot and Yolanda set out to get him fired. Meanwhile, Sofia is annoyed at her new neighbor for constantly playing loud music, until she meets him face-to-face.

Gabi and Sofia start working together, but things turn awkward when only one of them can land a coveted promotion.

Gabi is thrilled when she wins a local cooking contest using a recipe she got from her Aunt Chris. But when the contest organizers want to take a picture of Gabi and her aunt, Gabi is forced to go on a search for someone she hasn't seen in years. When Gabi finally tracks Chris down, she is surprised to learn that the reason she hasn't seen Aunt Chris in so long is her aunt has transitioned into her Uncle Chris. Meanwhile, Josh is forced to relive his childhood bowling trauma, and Elliot soon regrets joining Yolanda's poker game.

Josh shows up in Hawaii to find out what Gabi is doing with her fake husband Adam. But Gabi is desperate to escape back to San Francisco, only to have a hurricane trap everyone on the island. Meanwhile, Elliot is angry after he is saved from a life-threatening situation by Yolanda rather than his husband Alan.

Alan and Elliott are surprised when their new foster “child” turns out to be a teenager, who forms a quick bond with Gabi.

Gabi wants to prove to Josh that she’s doing fine on her own, so she leads him to believe she has a new job with famed chef Giada De Laurentiis. Meanwhile, Josh throws Yolanda a 50th birthday party, and uses the party as an excuse to check up on Gabi.