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Exclusive: Prisoner of Love’s Chelsea Holmes on being “The Prison Matchmaker” and bringing love behind bars

Chelsea Holmes smiles
Chelsea Holmes helps inmates find love on Discovery+ latest series, Prisoner of Love. Pic credit: Discovery+

Chelsea Holmes is bringing love behind bars on Discovery+’s new series, Prisoner of Love. The 42-year-old mother works as a school teacher by day, but the Prison Matchmaker found her true life’s calling while assisting on wrongful conviction cases.

Believing that everyone deserves a second chance, Chelsea hopes to break negative stigmas surrounding those incarcerated and give viewers an inside look into her unique business.

In this series, the self-described hopeless romantic is helping five couples find the connection they’ve been looking for with people serving time.

While Chelsea acknowledges that a relationship with an inmate isn’t conventional, the Florida native explains that “It’s a good one because then you learn about the person more.”

She continued, “You’re on a more mental connection before you get with them physically.”

Pointing out that it takes positive influences for inmates to not recidivate back to prison, “Now they have something to look forward to, this new relationship that they’ve started with someone,” Holmes added.

In a conversation with Monsters & Critics over Zoom, Chelsea explains what got her in her unique profession and why inmates deserve a second chance.

Check out our full interview below:

Exclusive interview with Prisoner of Loves’ Chelsea Holmes

Monsters & Critics: So Chelsea, you’re a prison matchmaker, tell me about that and how you discovered your passion in helping inmates find love.

Chelsea Holmes: It started when I was working wrongful conviction cases and had all these inmates constantly, like, reaching out to me, ‘Hey, do you think you can find, you know, my celly somebody to talk to?’

So I was posting all these, like, pen pal ads on social media and realized people were then, like, reaching out to me like, ‘Hey, can you find me somebody that you know falls under this criteria’ and I was like ‘Huh okay, so I might have something now’ and it just kind of like blossomed into a business.

M&C: Were you surprised that so many people were interested in dating men in prison?

Chelsea Holmes: Yes and no. No, just because you know I have that thing for, like, the bad boy in prison. But yes because it is a different relationship. It’s not your normal go out on dates every night and talk whenever you want to, [or] send them a text.

It’s a different relationship but it’s a good one because then you learn about the person more. You’re on a more mental connection before you get with them physically.

M&C: Where do you draw the line when it comes to the criminal history of which inmates can actually join the matchmaking service?

Chelsea Holmes: No crimes against women or kids is where I draw the line.

Now, so my business altogether is pen palling as well, so only some want to be matched. Some don’t, they just want pen pals. So the pen pals, I leave it open, [to] you know, murder even. I have some guys on there serving, double, triple life sentences but none of them have charges against women or kids.

M&C: What are some red flags you usually tell your clients to look out for when participating in these relationships?

Chelsea Holmes: If they try to fall in love too fast, which that’s a big one. You know, weeks of dating someone if they say ‘Oh my gosh I love you, I think I’m falling in love with you,’ that’s a red flag.

Also, if they’re asking for money or if they are out of your league. If you’re 60 years old and he’s 30 [years old] and he’s not normally somebody you’d date on the streets, why would you date him now? Like, how does that fit together?

M&C: On Prisoner of Love, Isa wasn’t sure about ultimately going for Devin. What did you tell her on the phone that ultimately encouraged her to give him a chance?

Chelsea Holmes: I think she was really conflicted because she was drawn to him physically. She was drawn to him mentally. They had this connection through writing and back and forth but it was the whole, she was scared. She was scared that he’s in prison, you know, she’s not, plus her parents.

She was concerned about her parents, but my thought is, we all know somebody in prison. You know, they’re in there because they committed a crime, they’re being rehabilitated, so they deserve second chances too. So I just told her, I was like, you just need to go with how you’re really feeling.

M&C: I know there are a lot of negative stigmas associated with your work, what’s one thing you’re hoping to change people’s minds about?

Chelsea Holmes: There are so many negative stigmas. I just like reading through social media and seeing like, negative comments that ‘this is a thing.’ This is a thing because they’re being rehabilitated. They’re in prison to pay for a crime that they committed and be rehabilitated to come out a better citizen.

So to be a better citizen and not to recidivate and go back to prison, it helps to have positive outside influences, relationships, it makes them a better citizen. So that they’re not wanting to get back into gang banging or you know, selling drugs or whatever they were doing that got them in there in the first place. Now they have something to look forward to, this new relationship that they’ve started with someone.

So I’m hoping that the public will open their eyes and see ‘Okay, these people deserve a second chance. This might be a weird way to do it but she is helping the community.’

M&C: What is it about Prisoner of Love that made you want to share your life with the world?

Chelsea Holmes: I think that I wanted people to see, not only that these people deserve a second chance, but I also wanted them to see that we’re just regular people. We that fall in love with people behind bars and that tend to date people behind bars, we’re normal people.

Like, I’m a mom, I’m a 42-year-old woman that lives you know, in Panama City Beach with two kids. I have a normal life outside of matchmaking and dating an inmate. We’re just normal and we just want everybody to see that this is okay. Just because we choose to date someone in prison, doesn’t define us [or] who we are as a person.

Prisoner of Love is currently available for streaming on Discovery+

Brianna is Bay Area-based reality TV lover and writer who has...read more

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