Jake and Dylan discover there is a betting pool in the office for how long their relationship will last. In an attempt to prove their commitment to their skeptics, they decide to have everyone over for dinner to show how happy they are together. Penny and Gavin bring separate dates in hopes of not being branded as a couple. In the end, the only thing they all know for sure is that relationships are not as easy as they seem.

Jake finds out that Dylan has an ex-husband and tries to keep cool until Gavin reveals who Dylan's ex-husband really is -- and Jake can't get him out of his head. Meanwhile, as Halloween approaches, Penny goes to a costumed wedding reception and brings along Frank, who finds that being in costume has extra benefits when he thinks he's found his very own Southern belle.