Heather and Tim meet a couple they want to socialize with, but Sophia and their son don't hit it off; Greg thinks he and Jen should take separate flights in case something happens to the plane; Matt and John take Gary out to meet women; and Matt's ex-wife makes a surprise visit.

When Greg and Jen slip away for a couples massage, the afternoon doesn't turn out to be as relaxing as they expected. Also, Tim, Heather and the kids have a contest to see who can accumulate the least trash, Colleen asks Matt to illustrate a children's book she is writing, and Jen helps Joan and John with their will.