Love Behind Bars: 5 Facts About Prisoner Matchmaker Chelsea Holmes

“I myself have a thing for bad boys that are incarcerated,” she admits.

September 08, 2021
'Prisoner of Love' matchmaker Chelsea Holmes

'Prisoner of Love' matchmaker Chelsea Holmes

Photo by: Discovery, Inc.

Discovery, Inc.

'Prisoner of Love' matchmaker Chelsea Holmes

By: Aaron Rasmussen

Chelsea Holmes is helping clients find love — with inmates behind bars. The Florida-based prison matchmaker and star of the new discovery+ series Prisoner of Love has said business is booming and especially took off during the COVID crisis when so many people were stuck at home and hoping to find a connection with that special someone. Ahead are five facts about Holmes and her unique job.

She Didn’t Intend to Become a Matchmaker for Prisoners

“It actually started during a continuing education course, where my professor encouraged us to broaden our circles,” Holmes said in an interview with TV Shows Ace. “I had previously volunteered with a wrongful conviction organization, and I thought it would be great to start a pen pal program with prisoners. So, I started by posting people incarcerated on social media, and people were constantly reaching out to me with questions, and before I knew it, I was offering to match people.”

Holmes Isn’t Surprised Some People Want to Date Prison Inmates

“I myself have a thing for bad boys that are incarcerated, so I kind of knew where most of them were coming from,” Holmes told Entertainment Tonight. Prisoners are often able to “date” and get to know prospective love interests on the outside via email and weekly video chats before possibly engaging in face-to-face prison visits.

Just How Does the Matchmaker Find Eligible Prisoners?

Holmes said she locates eligible prisoners through contacts within the prison system across the United States, and she has upward of 6,000 clients on the inside. According to the matchmaker, inmates, not her non-prisoner clients, pay for her services, often either through money they earn at prison jobs or through family.

The Matchmaker Also Found Love with a Man Behind Bars

Holmes grew close to a prisoner named Manuel after she spotted him while posting an inmate on a Facebook prison pen pal group. She told TV Shows Aces she found him attractive and “could tell he was smart” through what he said in his introduction. “I immediately wanted to write to him,” Holmes recalled. “He was the first prisoner I crossed the line with from pen pal to romance, and it was definitely a lot of fun!”

Holmes Isn’t Concerned About What Others Think

Holmes said those who truly know her are already well aware she’s going to do what she wants, including dating an inmate. Now friends and family have “seen a change with how happy I am,” she told As for everyone else? “I know there are a lot of people who will judge me and my life choices. We all make questionable life choices, but some people do it on TV,” she said.

Start streaming full episodes of Prisoner of Love now on discovery+.

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