In the present day the friends are at the funeral of one of their friends, whose death is being investigated by Detective Marjorino. Before the identity of the deceased is revealed, we're transported back to 1986, as Aaron, Samantha, Will, Craig, Carla, and Jenna are celebrating their high school graduation. We follow all six through the summer of 1986, and witness the formative events that alter their dreams and desires forever on the "1986".
Robert Palmer -- Addicted to Love, Mister Mister -- Broken Wings, Simple Minds
-- Don't You Forget About Me, Dream Academy -- Life in a Northern Town, Madonna
-- Papa Don't Preach, A-ha -- Take On Me, The Romantics -- Talking in Your Sleep, Cyndi Lauper
-- Time After Time, Bonnie Tyler
-- Total Eclipse of the Heart, Wham -- Wake Me Up Before You Go Go
After he is released from prison, Will discovers that the transition to life on the outside won’t be simple, especially when his former cellmate shows up with a “business proposition.” Samantha returns from London with second thoughts on the difficult decision she made there. Meanwhile, Carla visits Jenna in New York, only to find Aaron there, his torch for Jenna burning as brightly as ever. The investigation continues as Detective Marjorino traces the murder weapon to one of the friends on the “1987” episode.
The competition between Craig and Will for Samantha grows, causing Will – who now works for Craig’s father – to cross some ethical and legal lines. Samantha has more important things on her mind – she’s finally tracked down her daughter in New York. After the adoptive parents warn her to stay away, she and Carla hatch a plan to keep tabs on the child. The appearance of Jenna’s mother threatens to overshadow her movie premiere, and Aaron tries to mend his broken heart in Seattle. Detective Marjorino’s interest in the murder investigation is revealed to be more than just professional on the “1988” episode.
Bryan Adams -- Heaven, OMD -- If You Leave, George Michael
-- One More Try
A wedding brings out old rivalries as Samantha must finally choose between Craig and Will. At the same time, Will pays the ultimate price for the one crime he did commit when he brings down the family of a close friend. Aaron returns from Seattle with a secret, and Jenna puts her own career ahead of Carla’s. Detective Marjorino learns he’s carried a grudge against the wrong man for 20 years, and one of our friends receives an anonymous letter – from someone who claims to know who the murderer is on the “1989” episode.
Fine Young Cannibals -- Good Thing, Roxette
-- Listen To Your Heart, The Cure
-- Love Song, Fine Young Cannibals -- She Drives Me Crazy
Carla finds herself isolated, keeping secrets from both the new man in her life and Samantha. Craig struggles to keep his father’s business afloat, but Aaron, who is halfway around the world, may hold the key. Jenna and her mother have a moment to reconnect before tragedy strikes, and Will ships out to the Gulf War. In the investigation, the identity of the murder victim is revealed.
Social Distortion -- Ball and Chain, Skid Row
-- I Remember You, The Smiths
-- Please Please Please Let Me Get What I Want
Sam notices bruises on Carla, which she fears were delivered by her mystery boyfriend. Amy’s kidnapping forces Sam to tell Craig most of the truth involving her pregnancy. Aaron and Craig are in business together but Aaron gets an offer from an Internet company that he cannot refuse. Will returns from the Gulf War and has a final errand to do for his Army buddy, whose death he blames on himself. Marjorino gets a hot lead after interrogating one of the friends.
-- Losing My Religion, Jesus Jones -- Right Here, Right Now, James -- Top of the World, EMF -- Unbelievable
Things get tense when the six friends gather together to celebrate Thanksgiving 1992. Aaron’s date is co-worker Rachel, whom he doesn’t realize has an ulterior motive for wanting to come. Jenna’s movie-star husband joins her and it becomes obvious that this may be a marriage of convenience. Will brings his girlfriend Vanessa, his former Army buddy’s sister. Russell Brewster shows up and demands that Will be thrown out, still blaming him for the collapse of the Brewster Group. Meanwhile, in the present day, Detective Marjorino’s 20-year obsession for revenge against his father’s killer and now with the investigation of Samantha’s murder, are taking a toll on his marriage.
The friends gather at Samantha’s grave on her birthday to pay their respects and reminisce. In 1993, it’s Samantha’s 25th birthday and the friends plan to surprise her with a party but she cancels everything when one of the ER patients she released drops dead. Also in 1993 Craig is weighing his options on whether or not to run for state assembly and does some soul searching with Jenna at their high school where it’s “Jenna Moretti Day.” Aaron and Carla finally make plans to go out on a date but Pascale, the girl he met in Prague, shows up with a toddler she claims is his. Meanwhile after getting kicked out by his wife, Detective Marjorino asks for time off, away from the case.
The episode follows the friends through various events and seasons of the year 1994. The episode begins on New Year’s Eve, when Carla introduces her new boyfriend Peter to the group and Craig announces his candidacy for the state assembly. Flash forward to Craig and Sam’s son Henry’s third birthday, as Aaron lets Carla know he still has feelings for her and that Pascal has left him. Carla must decide if she still has feelings for Aaron or if she should pursue Peter. Meanwhile, Rachel, the secretary with whom Craig had an affair, won’t move and stalks Craig and his family. She also threatens to go to the press with the story of the affair, thus jeopardizing Craig’s political career. In the present day, Marjorino questions Rachel after he finds out that Craig and Sam filed a restraining order against her in 1994, and she becomes the latest suspect.
When something bad happens to Marjorino in an alley, he finds himself in the hospital. Will was there and helps by going with the detective in the ambulance. In the past, Sam and Craig decide to set Will up with Katherine Clark. They have a double date and Will and Katherine seem to hit it off. However, there is a secret lurking that may cause Will to run away. Carla is propositioned and she knows there is no way around it. Aaron and his wife have to go to couple's therapy and Jenna finds out about her boyfriend's secrets. Pascale shows up.
Craig's mother passes away and Henry is revealed to be part of the accident. In the past, Katherine and Will get serious and Will meets her dad. During a hunting outing, Will and Katherine's dad fight and the results are deadly for one of them. Carla and Jenna gossip and reveals that she and Peter are trying to have a child. Sam finds out Peter has leukemia. Aaron is put in charge of two little ones while balancing work. He calls Jenna for help.
Jenna moves in with Aaron to help take care of Chloe and Noelle, the two little ones. However, Pascale comes and demands to have custody. In the court case, it comes out that Jenna and Aaron are romantically involved. Carla stays by Peter's side as he battles leukemia. When they offer a bone marrow treatment, Carla goes to the claim's officer, but is propositioned to have sex with him for the money. She refuses and calls Aaron, but he is unable to help. Carla struggles to decide whether she is going to give in to the demands. Aaron is able to help and Carol shuts down the claims officer. Will learns what Amy is really up to.
Craig is turning 30 and Aaron wants to give him a party. However, things end up bad for both of them. Jenna gets a job and Sam helps Will search for Amy. Carla has a run in with someone from her past and things get interesting.