Plot Synopsis

PRISONER OF LOVE is a one-hour docuseries that follows prison matchmaker Chelsea Holmes, as she helps five couples navigate the roller coaster ride of dating someone in the big house and the unique struggles it presents. Finding true love isn't always easy, and now more than ever, struggling singles across the country are craving a romantic connection. But sometimes true love can't be found at the local bars because 'the one' is serving time behind them. Chelsea has been connecting with inmates for years through a pen pal program, and recently evolved it into a business matching hopeful singles with prisoners for the digital age. As Chelsea navigates her locked-up love affairs, her clients are trying to manage their own budding relationships with desperate desires for a life of love after a stint behind bars. Chelsea does all she can to give these singles the tools to make their relationships successful beyond prison walls, but are these convict connections built to last? Taking a leap of faith, below are the list of couples featured in Season 1 are:

Chelsea and Manuel: Not only is Chelsea Holmes a prison matchmaker, she is also a client herself! After she found love with an inmate through a prison pen pal program, she wanted to help others find the same success in their relationships. Chelsea never let herself cross the line from pen pal to romance with an inmate -- until she met Manuel. His rugged good looks and charming personality instantly attract her, and she falls hard.

Isa and Devin: College student Isa has always been a good girl. She's studying education in New York, but focusing all of her energy on her studies left her love life with a failing grade. Now, she's fallen for inmate Devin, and it's throwing her whole life into disarray. Her conservative parents can't find out, her friends don't approve, and even she isn't sure how bad-boy Devin fits into her long-term plans. But her heart is in it, even if her head is stuck between two worlds.

Brey and Arlette: Brey is best friends with Chelsea's son, and now that he's all grown up, he decides to give her art of matchmaking a try. Brey has always been a quiet creative, and hasn't had much luck introducing himself to women at bars or meeting potential matches through the apps. Once Chelsea shows him some of the beautiful female inmates looking for love, Brey jumps in with both feet and lands on Arlette.

Dexter and Yolanda: When Dexter first learns that his son, Brey, is considering dating an inmate, he is in disbelief. Dexter is old school, and can't understand why his son doesn't look for a traditional relationship the old fashioned way. After sitting in on Brey's first matchmaking session with Chelsea, this twice-divorced dad decides it might be time to break out of his comfort zone and try a new approach to dating, too.

Aluntra and Bryce: Though not one of Chelsea's clients, Aluntra and her fiance Bryce have been separated by prison walls for their entire almost four-year relationship. Now that Bryce's release is weeks away, Aluntra is ready for the two of them to finally get a fresh start and begin their life together. They have big plans to get married, start a family, and find careers in a new city, but Bryce's family and past threaten to hold them back. Aluntra has waited years to be with her beau, but will her patience run out?

The first three episodes of PRISONER OF LOVE dropped on Monday, August 30, 2021 on discovery+, with the streaming service releasing one more episode each Monday through September 20.
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PRISONER OF LOVE made its linear television debut on Monday, January 24, 2022 at 9pm ET/PT on Investigation Discovery. In the season opener, "The Prison Matchmaker," Chelsea Holmes starts a new career as a prison matchmaker after finding love with an inmate. She matches shy 21-year-old photographer Brey, and Bronx college student Isa falls hard for bad boy inmate Devin.