‘Prisoner of Love’ Matchmaker Chelsea Holmes Talks Finding Her Own Romance Behind Bars in New Series (Exclusive)

Chelsea Holmes is helping people find love where they might not expect it — and maybe finding it herself! The self-described “hopeless romantic” is helping five couples find the love they’ve been looking for with people serving time in prison in the new discovery+ series Prisoner of Love. Before Monday’s streaming premiere of the new dating show, Holmes opened up to PopCulture.com about how even she found love through her pen pal service Prison Love and Friendship,

Holmes first discovered her passion for helping people who are incarcerated when a college professor encouraged the class to begin expanding their circles, “thinking outside the box and meeting people you wouldn’t normally meet.” Beginning to form relationships with her pen pals, Holmes realized how important friendship and romantic connections could be for people serving time.

“You may go in with thousands of friends, but you come out and those people have forgotten about you,” she explained. “They’ve moved on in life.” Pointing out that recidivism rates for people who have personal connections outside are lower than those who are more isolated, Holmes said she’s taken on the role of family for many of the people she connects with a potential friend or partner. “A lot of people immediately think that just because someone’s in prison they don’t deserve happiness,” she said. “And that’s huge.”

When Holmes first saw a photo of Manuel in her pen pal group, she admitted she thought he “was a little cutie” and decided to “shoot [her] shot” and ask if he wanted to be her pen pal. “I never had any other thoughts other than I thought he was cute and wanted to be his pen pal,” she shared, but after their first conversation, she realized they had a lot in common.

Having a relationship with a prisoner can be difficult for many reasons, but Holmes said engaging in her own locked-up love experience has given her a “better perspective” on matching, including a better eye for when the inmates aren’t truly looking for a connection. Her own love life has invited a lot of skepticism from friends and family, but Holmes doesn’t pay it any mind.

“Number one, this is my life, we already know I’m gonna do what I want to do anyways,” she recalled telling her loved ones at the start. “But they’ve also seen a change with how happy I am.” As for the rest of the world getting a front-row seat to her dating life, Holmes shrugged, “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.” You can stream three episodes of Prisoner of Love now on discovery+, with three additional episodes dropping every Monday.