At the start of 1994, Craig announces his run for the State Assembly, but a past affair emerges, and the woman involved appears in the present to give Marjorino's case a turn, or maybe two.

Sam's 1993 birthday includes a fatal error at the hospital, a bombshell dropped on Aaron, a confession from Jenna and an important encounter for Carla.

Sam and Craig host Thanksgiving 1992, where two unexpected guests create tense moments as an affair is revealed, a grudge is held and a marriage of convenience is no longer.

In 1991, Will visits Jenna in Hollywood en route to completing a mission; Craig is disappointed by both Aaron and Sam; and in 2005, the gun resurfaces and another cryptic note is received, this time by Will.

Craig struggles to keep his dad's company afloat; Will prepares for international travel; Carla gets a title Sam covets, and a warning; Jenna comes home to visit her ill mother; and Aaron finds inspiration in Prague.

The six friends gather for a wedding; Brewster suspects Will of subterfuge; problems arise with Carla's job and one promised to her by Jenna; and an old truth throws Detective Marjorino for a loop.

To make a case for retrieving her baby in 1988, Sam needs help from Will, who breaks the law to do so without knowing her end goal; Jenna's mother helps celebrate her first movie role; and Craig declares to Will his intentions regarding Sam.

In 1987, Sam and Carla get surprises upon their return from London; Aaron has "mix-ups" with Jenna; and Will gets advice from a former cellmate.

Carla (Chyler Leigh) is cornered at an old friend's funeral by a detective (Mathew St. Patrick) interested in her clique's 1986 high-school graduation and the events that may have led to the deceased's murder.