FLASHBACK TO DAMON’S LIFE IN 1970s NEW YORK / THE BAND DEAD SARA PERFORMS — Realizing that Elena (Nina Dobrev) needs some time away from Mystic Falls, Damon (Ian Somerhalder) takes her to New York City, where he lived and partied hard in the 1970s. When Rebekah (Claire Holt) also shows up in New York, she’s impressed with Elena’s secret agenda. Flashbacks reveal Damon’s hedonistic life in the underground club scene and a complicated encounter with Lexi (guest star Arielle Kebbel). Meanwhile, Caroline (Candice Accola) and Stefan (Paul Wesley) try to convince Klaus (Joseph Morgan) that it would be in his own best interest to help them track Silas down, and Bonnie (Kat Graham) struggles to keep her grasp on reality and do the right thing. Garreth Stover directed the episode written by Brian Young & Charlie Charbonneau (#417).
—  4x17 ‘Because The Night” snyopsis 
CHARLIE BEWLEY FROM “TWILGHT” GUEST STARS AS ONE OF THE FIVE HUNTERS — On the island, Damon (Ian Somerhalder) has an ugly run-in with a Hunter named Vaughn (guest star Bewley), and realizes he is one of The Five. Stefan (Paul Wesley) confesses his true feelings about the possibility of becoming human again to Elena (Nina Dobrev). When a stunning new piece of information about the cure is suddenly revealed, it changes the stakes for everyone. Jeremy (Steven R. McQueen) helps Bonnie (Kat Graham) recognize what is real and what is an illusion, and Shane (guest star David Alpay) is comforted by a woman from his past, Caitlin (guest star Camille Guaty, “Prison Break”). Back in Mystic Falls, Caroline (Candice Accola) and Tyler (Michael Trevino) find that their attempt to translate the code on the Hunter’s Sword is futile without help from Klaus (Joseph Morgan), who has his own reasons for solving the puzzle. Claire Holt also stars. Chris Grismer directed the episode written by Jose Molina (#414).
—  4x14 ‘Down The Rabbit Hole’ Official Snyopsis
LET’S MAKE A DEAL — Damon (Ian Somerhalder) and Stefan (Paul Wesley) try a brutal new approach to provoke Elena (Nina Dobrev) into turning her humanity back on, and Caroline (Candice Accola) is frustrated when her attempt to intervene backfires. When Elena figures out a way to call the Salvatore brothers’ bluff, they call for backup from a surprising source. Matt (Zach Roerig) gives Rebekah (Claire Holt) some unsolicited advice on her life choices, and she tries to help him in return. Caroline has a confusing and dangerous encounter with Klaus (Joseph Morgan), and Katherine (Nina Dobrev) is suspicious when Bonnie (Kat Graham) makes her an offer that she promises will benefit them both. Darnell Martin directed the episode written by Michael Narducci & Rebecca Sonnenshine (#421).
—  4x21 ‘She’s Come Undone’ Official description 
COLLEGE DAYS – After spending the summer enjoying her passionate relationship with Damon (Ian Somerhalder), and making sure that Jeremy (Steven R. McQueen) is adjusting after his return from the dead, Elena (Nina Dobrev) is thrilled to move into the dorm at nearby Whitmore College with her new roommate, Caroline (Candice Accola). Still believing that Bonnie (Kat Graham) has been traveling all summer and will soon join them, Elena and Caroline are surprised when a student named Megan (guest star Hayley Kiyoko) shows up and announces that she will be sharing their dorm room. Katherine (Nina Dobrev) makes an unexpected appearance at the Salvatore house and pleads with Damon to help her now that she is human and vulnerable to her enemies. Matt (Zach Roerig) and Rebekah (Claire Holt) return to Mystic Falls after spending a wild summer in Europe, where they met a mysterious beauty named Nadia (guest star Olga Fonda). Elena can’t shake the feeling that something is wrong with Stefan (Paul Wesley), and Silas (Paul Wesley) makes a terrifying appearance at the “End of Summer” party in the town square.
—  Officialy snyopsis for 5x01 ‘I Know What You Did Last Summer’ 
A FRAT PARTY AND A FLASHBACK TO 12TH CENTURY ITALY — Damon (Ian Somerhalder) goes with Elena (Nina Dobrev) and Bonnie (Kat Graham) to visit Whitmore College, where Professor Shane (guest star David Alpay, “The Borgias”) is taking over the Occult Studies classes formerly taught by Bonnie’s grandmother. At a fraternity costume party, Damon takes advantage of the wild scene to give Elena a lesson in choosing a victim. Rebekah’s (Claire Holt) attempt to buy Matt’s (Zach Roerig) forgiveness falls flat, but she is intrigued by unexpected news from Klaus (Joseph Morgan). When Stefan (Paul Wesley) questions Klaus about Connor’s (guest star Todd Williams) motives, Klaus reveals a long-ago encounter with a powerful group of vampire hunters, but it’s Rebekah who delivers the information that stuns Stefan. Joshua Butler directed the episode written by Brett Matthews & Rebecca Sonnenshine (#404).
—  4.04 ‘The Five’ Official Synopsis 
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