When Heather tries to become Tyler's cool best friend, things take an awkward turn. Also, Jen and Greg get their first overnight away from Lark; Matt and Colleen regret returning their wedding presents for cash when they learn what John and Joan hid inside their gift; and Tim goes overboard when keeping a watchful eye on Samantha and her boyfriend.

Jen and Greg decide to take turns dealing with her annoying parents when they come to visit. Also, when Tim and Heather chaperone Samantha's dance, Heather runs into an old flame; Colleen cashes in the many "love coupons" Matt has given her as gifts over the years; and Sophia digs up disturbing information when she investigates the family lineage.

Jen and Greg go to great lengths to find the perfect babysitter for Lark. Also, John becomes testy when shopping for a mattress and Joan realizes the unusual source of his aggravation; Heather learns information about Samantha's boyfriend that she isn't sure she should reveal; and Matt believes he may have a history with Colleen's sister after he meets her for the first time.

Tim and Heather plan a surprise birthday party for Samantha, but the night takes an unexpected turn when she doesn't come home alone. Also, Matt and Colleen learn their surrogate can no longer carry their baby; John and Joan decide to learn Spanish for their next adventure; and Jen and Greg have to find a way to keep their secret from the family.