Jane and Alex's parents throw a big celebration to commemorate the 20th anniversary of the family mattress business, and Jane agonizes over coming up with an amusing toast to spring on her humorless dad. Meanwhile, Alex tells Dave that her parents are unaware that they are once again bedfellows, and Max goes looking for a new BFF since Penny's tied up in her relationship with Pete.

The third Kerkovich sister, Brooke, is the alpha sister of the group, and Jane has the daunting task of planning a wedding for her more perfect and exquisite older sibling. Meanwhile, Brad is having a tough time himself dealing with Brooke's equally more perfect African American fiance, Elliot, and Alex and Dave have a big secret they're hiding.