[dramatic music playing]
[Isa] I've kissed so many frogs in my life,
they're still frogs.
I just can't wait to find my future husband
and start our life.
[dramatic music playing]
I'm trying to see my baby, you know.
Guess who got a letter from her boyfriend.
Bryce is my soul mate.
I feel like I hit the jackpot with this guy.
[dramatic music playing]
I'm a prison matchmaker.
I'm just looking for some ladies to just hang out with.
I'm looking for someone fun, cool.
I'm very outgoing.
Swipe low just hit my page out.
Just hit me up.
[dramatic music playing]
[woman] I am headed to meet-up Bryce.
[dramatic music playing]
[man speaking]
You're very welcome.
Chelsea I love you.
I'm ready to get married.
Dance 'till our legs give out.
I can't wait to snuggle.
I want to be in love.
I need to be in love.
[dramatic music playing]
Sometimes I'm so confused.
This is the lowest, right here.
He didn't care.
She'd go crazy on me, she could cuss me out.
That's a big red flag in my book.
[woman] Today, we are getting tattoos of each other's names.
- What? - Why did you do that?
[woman] It's been a long four years
and it has all lead up to this moment.
I'm just waiting for him to walk out the door.
- [woman screams] - [man] Hello!
[dramatic music playing]
[Chelsea] My name is Chelsea.
I'm 42-years-old from Panama City Beach, Florida.
I'm a school teacher by day
and I have a unique hobby by night.
[man] IDOC number, 9 [bleep] 5, look,
I'm feeling all right.
I'm a prison matchmaker.
Make it out soon, so hit me up. All right.
I'm looking forward to hear from you. Bye!
[Chelsea] The girls are gonna like him
because he's got personality.
I've been writing pen pals for years
and it just dawned on me,
all these people that are single
stuck in prison with nobody to talk to, I thought,
"Wait a minute, this could definitely be a business."
Okay. And what age range are you looking for?
Got you.
Masculine.
So I started taking clients.
Their stigma, a lot of people have with,
"Ooh, they're, they're in prison."
But they're there trying to better their life
and, you know, a lot of these guys are smoking hot.
[Manuel] Well, hello Chelsea.
Hello love.
I'm in a relationship with an inmate, his name is Manuel.
Did you get a rack?
- I did. - Yeah?
I did, I did.
I'm getting big, actually.
I'm losing my cakes.
- Yeah? - How about that?
You're not gonna have nothing to hold on.
Don't be too skinny babe.
I was in shock when I realized that I had feelings for Manuel
because that's not me, I've had many pen pals
over the years and never fallen for any of them.
But, yeah, I've fallen for Manuel,
and he's super attractive, he's got really big muscles.
I hate not been able to talk to you some days,
it really drive me nuts.
I needed to hear your voice.
Oh, my God.
Uh, I've been pouty lately, I'm not even gonna lie.
I know, I can tell.
Look, if they can work for me.
You know Chelsea, I love you.
You know what, I love you too.
Listen, fool, I love you too.
It can work for anyone.
I've always wanted to help people ever since
I was little rescuing puppies,
and kittens, and bees.
So I'm not surprised to find myself prison matchmaking.
So with conjugal visits,
you have to actually be married to the person.
It feels like this is a natural progression for me.
[Keith] My name's Keith, I'm 21,
by the way, I'm a virgin,
I'm looking for that special girl to pop my cherry.
He's a cute kid, he's gonna do really well.
Oh, it's gorgeous out here today.
It's beautiful out.
[Suz] Just gorgeous.
I'm glad you came by, mom.
Oh, I've been wanting to have a good conversation with you
- not just on the phone but... - [Chelsea] I know.
[Suz] We both got a lot going on.
[Chelsea] And I feel like with all this, like,
pen paling that I've been doing, like,
my time is just so occupied.
My mom and I are super close but my mom has no idea
that I'm currently dating an inmate.
So I'm... I've got all these guys now, like, writing me,
all the time, and some of them
is just like they pull on your heart strings like...
Hmm, I can imagine.
[Chelsea] There's this one guy and he's like...
he's like almost eighty and he's been in there
for like twenty years, and yeah,
he did something really bad but he's little and old.
There you go. That rescue mentality.
Chelsea has always been, pick up a stray cat,
pick up a rescue puppy, she has such a tender heart.
So here's the thing,
I did form a really close relationship
with this one guy, Manuel.
- Uh-huh. - [Chelsea] Um, he's great.
He's a great guy, he's smart, um, he's my age,
locked up in Idaho,
and now it's like telephone conversations,
but I see, like, potential with him, you know,
I could see him being somebody
I could have a relationship with on the outside.
- I know. - That's concerning.
Does he have children?
He does have kids, yeah.
Are you supposed to meet him, when is he getting out?
[Chelsea] He gets out at the end of December...
- Oh, that's soon. - Uh, yeah.
[Suz] What the hell?
You know, I thought this was a pen pal?
You said... You didn't tell me
anything about dating somebody.
Now he has been in prison a few times.
[Suz] Oh. Drugs?
[Chelsea] Drugs and grand theft.
- Oh, my goodness. - [Chelsea] He was...
But he's humbled himself this time.
So I can see, I don't... I know you don't wanna hear it
but I can see him being somebody
I could fall in love with
and he's the first one I've ever felt this way for.
So, it sounds to me like you're sort of already
- on the brink of that. - [Chelsea] Yeah.
- Would that be accurate? - Yeah, absolutely.
[Suz] For whatever reason,
she likes him but Manuel to me is a stranger.
Is Manuel gonna be the kind of person
that's gonna be good to my granddaughter and my grandson?
Okay. Well here's one of my concerns,
they have to survive in there,
and sometimes that means they become violent
when maybe their charge wasn't violent.
And you say he loves children
but obviously he didn't care enough
about his own children to do right.
I think we all make mistakes and, you know,
everybody deserves a second chance.
You couldn't just like one of those doctors
that's been asking you out all these years?
I'm sorry, but, I mean, it's my question, you know,
what's the appeal?
Is it because he's needy and because you feel like
you need to rescue him?
Because that's no basis for a relationship.
You can't help who you fall in love with.
And you don't think there's any possibility
of him conning you?
I mean, for what?
How's he gonna con me?
I don't have any money.
How do you know he's not videoing
with a dozen other women?
I don't.
But I can think of many guys that I've, like,
dated in my past who had one or two of us, you know.
That's just a chance you're taking?
[Chelsea] Yeah.
We'll see is my attitude right now.
[dramatic music playing]
[Isa] I'm Isa, I'm 21-years-old,
I am a first generation college student.
Born and raised in the Bronx.
My life is pretty normal,
somewhat,
but then I met Devin.
Devin is my bear.
Like, he's big but he's such a softy.
I do see a future with Devin but one thing about him
is that he's never met me in real life.
[woman] This is a prepaid call from an inmate
to the [bleep] Correctional Institution.
- [Devin speaking] - Hello, hi.
[Devin speaking]
[Isa] I first met Devin when I was researching
for a school project and I came across
Devin's video on a pen pal website for prisoners,
and I thought, "Oh, my God,
he really wants me to write him back."
And, you know, and really talk to me,
and then I got a phone call from Chelsea
and she persuaded me to actually
really give Devin a chance.
Four months later, our relationship has expanded.
[Devin speaking]
[Isa] Devin told me that he's in prison
because he was in the vehicle with someone
that had an armed weapon and it went off,
and he got four years because of that,
but I see Devin for who he is,
he's got goals and when he comes out,
he expects to really accomplish those goals
which is what I really love about him.
[Devin speaking]
[Isa] I never expected to date an inmate,
I expected to date a normal man,
if my parents did find out
that I was talking to an incarcerated man,
they would think that I'm setting myself up
for a murder.
I'm still trying to figure out what is it about this man.
[Devin speaking]
Okay.
Sorry mom.
I'm Brey. I'm 22-years-old
and I'm a photographer.
I mean, show something, be like, "What's up?
What you reckon?" There you go.
I love anime, I love videogames.
People will be like, "Oh, no, that's nerdy."
But that's me.
I may come off shy to some people but, you know,
I'm just kind of to myself a little bit
but I'm a, you know, I like to say like a kind-hearted,
just goofy person.
I first learned about inmate matchmaking
from my boy, Jacob, that's Chelsea's son.
He was just like, "Yeah, my mom's doing
this little, like, dating thing."
And she came to me one day, she was like,
"Hey, are you trying to find somebody?
You looking for love, hon?"
And I'm just like, "Yeah."
It was like, "I'm trying to find some love
and it's, like, it's been a minute."
I don't know.
Because I need to step out of that comfort zone,
so today I'm here at the pier with Jake and my boy Marion,
and I'm breaking the news,
this is something I wanna go through with.
- Talked to your mom yesterday. - [Jacob] Okay.
She got me into some matchmaking.
- Got you. - Yeah, you already know.
Matchmaking?
About what?
His mom's doing a little matchmaking service
with, uh, inmates.
Why is your mom...
Why is she doing this?
She's doing it as a... as a business, man.
It always feels very interesting
trying to explain what exactly my mom does, uh,
it gets a lot of interesting reactions to say the least.
So these girls are in jail right now?
These girls are in jail currently right now.
Uh, dude.
I don't know.
Matchmaking with inmates that's, like,
really still in jail?
Like, this is crazy.
Do you feel like this is a little extreme, like...
You know me man, you know, I'm a shy person, you know,
it's a really hard for me to, like,
mix and mingle with people.
See I know you shy but, like, take a public speaking class.
I mean...
Ever since I've known Brey,
the one thing he hasn't really grown out of is that shyness,
like he's always been a little bit, like, reserved.
And this is not normally Brey's behavior.
I'm glad to see Brey
sort of starting to poke out of his shell.
Uh, that's what I'm saying man,
I ain't gonna lie, I did not expect this from you.
There's something about it man, it's just...
[Jacob] Yeah.
[Marion] This does not scare you, like,
she probably, like, maybe more violent?
I'm not gonna lie, a little bit, I'm a little nervous.
- [Marion] You nervous? - Yeah, a little nervous
but as long as she's willing to change.
Everybody has a chance to redeem themselves so...
[Brey] Everybody makes mistakes in life,
you know, so.
[Marion] I don't know man, like,
that's a... that's a hell of a mistake.
I know going for someone in prison,
everyone is gonna say some off the wall things about it
because it's not the norm but at the end of the day,
I'm still gonna do what I wanna do.
I wanna try something different man, I know...
I know love's out there, you know,
this is just one of the ways I wanna try and find it.
This could be an absolute disaster, like,
Brey could get seriously hurt physically, mentally,
he can, you know, he's vulnerable.
It is... It is very... Well, it's just kind of hard
to wrap my mind around, I'm not gonna lie to you.
Have you told your dad about this?
No, not at all.
Me and my dad, that's my dude right there,
that's my partner in crime.
I'm really nervous on how my dad's gonna react,
my dad's probably gonna look at me, like,
"Man, this boy's crazy."
I don't know. I don't...
[upbeat music playing]
[Chelsea] Tonight, I am meeting up
with my best friend Jonathan.
I wanna update him with what's going on
with me and Manuel.
Jonathan is brutally honest
and I'm sure that
he's going to have a lot to say.
I have so much to tell you
about Manuel,
- the guy that's locked up. - [Jonathan] Mmm-hmm.
You know, that I've been talking to,
like, he is fine.
Can I see?
So, super good looking,
muscly.
So is this like a serious relationship?
[Chelsea] This is like pretty serious, yeah.
- This is not... - On a... On a level of, like,
one to ten, where are we?
I'd say we're, like, an eight,
like, we're in pretty deep.
Chelsea jumps from relationships so fast,
so although Chelsea thinks Manuel is here
for the long term, like, I know for a fact Manuel
is, like, one phone call away from getting dumped.
I'm just, like, "All right girl,
call me tomorrow and let me know
who you have in store next."
So he's where?
- He's in Idaho. - [Jonathan] Idaho?
- Udaho? No. - [Chelsea] Udaho.
Mama.
You de prisoner.
No.
Um, but he has an out date, obviously,
um, the end of December.
Okay.
[Chelsea] So...
plan's will probably be to get him.
Like, you go there to get him?
[Chelsea] To, like, yeah.
- So I mean... - [Jonathan] Has he, like,
walked you through his arrests?
He's been arrested a bunch of times.
About how many times?
[Chelsea] Like, a bunch, um...
On one hand?
- Maybe. - Two hands?
Maybe two.
[Jonathan] The fact that Manuel has this rap sheet
that is as long as a CVS receipt is concerning.
I support the fact that she wants to try something new,
I support the fact that she wants to date an inmate.
But maybe get someone that ran a stop sign.
You Insana Girl.
So, like, what was the, like,
I see myself with a future with someone that's in prison?
[Chelsea] I think it's because when they're locked up,
obviously, if they're out here,
you're gonna get sexual super-fast, right?
- [Jonathan] Yeah. - Well, in prison,
you can only get sexual a little few ways
that's gonna be some dirty letters
or some nasty phone calls.
Have you sent him any pictures of...
Or videos of yourself, like, can you do that?
Not nasty, nasty but...
You're just, like, "Ooh, look at me. Like, yeah."
You know, just cute,
but everything's covered.
I don't know.
Chelsea saying that, like, sending nudes is not allowed,
it's just, like, break the rules, girl.
Get the [bleep] pic, like,
we need to know what you're working with.
- Yeah. - [Jonathan] So, do you guys,
like, when you're talking,
do you just explain, like,
my boobs are, like.
Can you hear me saying some crap like that?
- [Jonathan] I don't know. - No.
I do lose interest with guys pretty fast.
So with Manuel, just building it up,
it's pretty special and different, you know,
even though he is really sexy, I do care about him.
Has he done anything yet, like, you know, you usually,
like, you find something wrong with, like,
a guy and then you're, like, "Ooh, I'm out."
- Has he done anything? - No.
She is, like, a relationship hopper
and, um...
I hate that for her because
she's so loving, so caring,
but I think that she's, like,
she's scared to, like,
have, like, uh, a hardcore commitment.
So going for, like, uh, inmate that is literally
locked up is not surprising to me.
She doesn't want to break that wall down
and let someone inside.
[Chelsea] He's just like easy to talk to and he cares.
Except, I haven't heard from him in a few days,
but I think that might be, like, due to, like,
a lockdown because they have, you know, it's prison,
so there is times where he doesn't get to talk to me.
Like, I've messaged him, like, non-stop and nothing.
- That's never happened before? - No.
Usually I hear from him multiple times a day.
He's literally doing to you what you typically do
to other people,
ghosting them, but in...
We don't know that he's ghosting me.
He's not talking to you.
That's a ghost if I ever seen one.
Woo, woo.
[upbeat music playing]
[Isa] So I'm meeting Aliyah today
in my favorite coffee shop,
because I really needed to talk to someone about Devin.
Aliyah knows that I've been talking to Devin,
but she doesn't know that it turned serious.
- You know. - You stopped updating us.
I meant to, like, update y'all.
But, like, I was just like,
"Wait, this is getting out of hand." I'm, like,
I don't know what you guys are gonna think now.
I'm confused because I didn't know
that you actually liked him.
Well, this has escalated.
You are crazy.
I don't think that I ever expected Isa
to date an inmate.
So when she told us about it,
we were kind of, like, "Ah, okay."
Is he talking to anyone else?
No. Like, he calls me every day.
[Aliyah] Oh, my gosh.
So he sends you videos?
- He does. - [Aliyah] Let me see.
[Isa] This is what he says.
He's, like, "Just thought I'd send you something."
[Devin speaking]
Has he said that he loved you yet, like, outwardly?
He's very in love.
[Aliyah] Wow. He's moving so fast.
[Isa] He is.
Are you in love too?
Love is a very strong word.
Um, I do care about him.
[Aliyah] I do think that it's a little scary
on her part that him moving so quickly,
he's, like, investing a lot in her.
So, like, I'm worried that he's going to be,
I don't know, like, hurt by her or angry with her.
We don't really know how he's gonna react
and we don't have a lot of background on him
to know, like, you know,
what he would be like in that situation.
This happened so quickly though.
It's, like, you just started talking to him.
That's why I was, like, at first it was a joke
and now it's, like, serious.
So we're all, like, "Ah."
[Isa] Exactly. But I...
Does it make you nervous?
It does make me nervous.
I wake up every day and I'm, like,
how did I get into this?
So have you told that your parents yet?
[Isa] No.
You know, Dominican moms love to judge.
They'll just be, like, are you on drugs?
Is the bar that low for you?
His tattoo on his chest says heartless felon.
Oh.
- [Isa] Yeah. - Okay.
I feel...
It's so much sometimes.
I know that I shouldn't worry about what others say
because it is my life, but sometimes I do worry
and I'm, like, this is not normal.
Obviously, there's, like, reservations
because you don't know anything about him.
[Isa] Yeah.
You only know what he tells you.
[upbeat music playing]
[Brey] Today, we're going to the barber shop
and me and my dad are gonna get a cut.
- [Dexter] Hey. - [man] What's up, fellas?
Haven't seen you guys in a long time.
- Yeah. - [man] What's up man?
[Dexter] Yeah. Good.
[Brey] I'm gonna tell him
about this prison inmate situation
that's got going on.
So, what we doing today, getting a little off the top?
Oh, yeah. A little off the top. Yeah.
Just shave it up, you know, real good
and trim up my beard a little bit.
I'm really nervous on how my dad's gonna react
but this is something I wanna go through with.
Got something interesting to tell you.
Recently, I've been, um, talking to Chelsea.
She has this, uh,
little business going on
where she does matchmaking.
[Dexter speaking]
It's, like, I guess you could say that.
- Yeah? - [Brey] Yeah.
Yeah. Kind of, like, a little dating app.
But here's the thing.
I'm finding someone that's locked up.
Hold up, man.
When you say locked up, you mean, like, in prison?
Incarcerated. Yeah.
What the [bleep] are you thinking, man?
Have you bumped your head or something?
[Dexter] Hold up, man.
Bro, all these women here in Panama City,
and you wanna try to find love in prison?
I mean, why not?
[Dexter] That's [bleep] don't make no kind of sense, man.
I mean, Brey has always been the quiet,
reserved and, you know, shy
to say that, you know, "Hey, I'm gonna date,
you know, inmate, an inmate."
I'm like, "Okay. I wasn't ready for that."
When I was your age, man, I would just go to a bar, man,
and, you know, if I saw someone I like,
I just go up and, you know, talk to 'em.
I just want to try a different approach to it all.
Yeah. Well, yeah, girls being behind the bars.
[laughter]
Oh, yeah, it's gonna... it's gonna be different, all right.
[Brey] It's gonna be different.
I'm a very introvert person, it's just, like,
my dad's very social. So, it's just, like,
you may meet one in a bar.
If I'm in the bar, I don't even think
I'm approaching anybody,
uh, my game is a little off,
I'll be honest with you, my game is off.
Man, me and Chelsea gonna have to have a little talk, bro.
Have an open mind, open heart to it. So...
Just don't get no open chest wounds.
That's all I got to say. [laughs]
[upbeat music playing]
Hi. Um, usually at this time,
Devin does call me.
Today, he sent me an email.
So I'm gonna read it to you guys.
He says, "My beautiful wife,"
He calls me, his wife. [laughs]
"I hope you have a good day at work
just know your husband is thinking about you."
Obviously, he does know that I really care about him.
He wants me to speak to his mom.
It's very important to him, you know,
because if we are gonna be serious,
he wants me to speak to her.
Sometimes, I do wake up with mixed feelings
and I think to myself,
"Wow, this is, like, actually happening,
like, am I actually, like,
really talking to an inmate, is this a dream?"
I never knew that it would escalate to this.
I'm... Every day I just wake up
and I'm just a little bit confused about everything.
So, good night, guys and I will keep you updated.
[upbeat music playing]
- [Chelsea] Hey. - [Brey] Hey.
[Chelsea] How's it going? Welcome.
Brey is like my second son.
He has been best friends
with my son Jacob since they were little.
He's a common fixture in my household.
He knows where all my groceries go.
That's how close he is.
He's a great kid,
and I am excited to match him up with somebody.
- Good to see you. - [Dexter] We got a lot of talking to do.
- [Chelsea] Yeah, we do. - My son dating a inmate.
I'm still, you know, in shock about it,
so I don't really know what to expect
and I've got questions of my own
I wanna ask directly to Chelsea.
- This is my son. - I know.
Okay. He's a grown man, granted,
but when he laid it on me that he was trying
to get matched up with somebody from prison,
my antennas went up.
How do we know that they're not just using this
as an opportunity to, uh, scam somebody?
[Chelsea] You got to be smart about it.
People can also scam me on the street.
[Dexter] Brey is kind of a, uh,
hip nerd type, you know, of guy.
He's rather shy.
I guess my biggest concern is,
you know, some of the women may have,
um, experienced, you know, a little more than him,
may try to take advantage of him.
So what are, like, some of the red flags
- to look for? - [Chelsea] Well, some of the red flags
to look for is if she starts off
right off the bat after a couple of weeks
that she loves you.
- Okay. - [Chelsea] I mean, you don't love me, right?
- [Dexter] No. No. - You don't know me.
How you love me in two weeks?
Or if she says send me money,
- uh, it's never, um... - [Dexter] Right. To put on the commissary and stuff.
- [Chelsea] Mmm-hmm. - Yeah.
You just don't want to give too much...
[Dexter] Give too much too soon.
- [Chelsea] You got it. - [Brey] You know, it could go bad,
but this is a big opportunity for me to, like,
you know, step out of my shell.
The other relationships that I've had,
they haven't really been all that great.
I just wanna try something different.
I can't guarantee that I'll be there
to help break through it when he's, you know,
going through the process of learning about them.
[Dexter] I would never imagine in a million years
that my son would be getting matched up with an inmate,
um, I'm still trying to digest it.
This is my life. I really could care less
when anybody else has to say about it, so,
you know, if I wanna go through with it,
I'mma go through with it.
[Chelsea] Okay. First, this is Cynthia.
[Brey] Cynthia. All right.
- She's from Idaho? - [Chelsea] Yeah.
[Brey] Crime. Theft,
possession of controlled substance.
Nice, wholesome girl, huh?
- Yeah. - Age...
- Chill out, pop, chill out. - Okay.
[Brey] "I was your typical
All-American high school student.
I went straight to college
and that's when I met a boyfriend
who introduced me to drugs
and my life went all downhill from there.
I come to prison, I get clean and sober
and I find myself again.
I like to make people laugh.
I'm always playing pranks on people, even cops.
I take really good care of myself.
I work out every day. I love sports.
I plan on getting out, reconnect with my family,
going back to college,
and finding a real future
away from addiction."
I like Cynthia, she seems pretty cool.
She, to me, I feel like
she's really not gonna fall back
into the same pattern.
[Dexter] She's actually just, like, your girl next door,
you know, with charges.
[laughs]
Okay. So now,
- Arlette. - [Brey] Arlette.
- [Dexter] Oh, she's pretty. - [Brey] Okay. Yeah. She cute.
I see, you know, got the glasses
- and everything, like me. - [Chelsea] Mm-hmm.
[Brey] She's 22.
Loves movies, dancing, and being adventurous.
Crimes,
Aggravated battery, grand theft,
grand theft by possession.
- Ooh, boy. - Got some charges.
Yeah. Yeah. I already know you're looking at me like,
they are incarcerated.
Well, them was some is real charges, bro.
- I mean, they're in prison but it just, like... - [Dexter] Yeah.
Those are stuff that they've done in the past.
I'mma be the good influence. You know what I'm saying?
"I was born in the Philippines.
My center wasn't family. It was friends.
Clothes, drugs, booze became my daily routine.
I'm 22-years-old.
I'm willing to change and go back to the right path.
I really want a guy who's adventurous,
who can communicate with me, and someday have a big family.
I hate all those and I literally can't stand
when someone isn't taking care of their own hygiene.
Like, let's smell sexy together
and redefine the perfect duo."
Okay.
I'm excited to start like talking to 'em and everything.
I'm an introvert. So, it is very hard to like,
just come up and like start a conversation.
I don't know. It's been a minute
since I had this one-on-one with somebody.
So it's like, I'm excited.
- I actually like Arlette. - Okay.
The fact that she said she likes to dance
- that really caught me. - [Chelsea] I knew you.
As soon as I saw that I was like, "Mmm-hmm.
Yeah, that's all Brey. Right there."
You got to have the good music and everything.
Got to get the move in, yeah.
What about you, Dex?
How you feeling?
I'm beginning to understand it more now.
Once you put a face to the letters,
it's kind of a game changer
because now it's not the unknown,
you know, scaring the hell out of me.
I do empathize.
Everybody makes mistakes. And sometimes you got to pay,
um, the penalty for your mistakes.
Well...
why don't we start searching for you?
Just keep... To get some options going.
You're not dating anybody? You're single?
[Dexter] Uh, I don't know. Uh...
You got to do this, man.
You got... You got to find you some love out here.
You're, how old? Fifty something,
- you got to find something. - I'm in my late 50s.
Okay. Late 50s. Yeah.
Listen, you wouldn't believe
there's all ages and all types.
Mmm-hmm.
Let me think about it.
Don't knock it until you try it.
[upbeat music playing]
[Isa] So today, I'm doing a video chat
with Devin's mom for the very first time.
I'm excited to actually talk to her.
You know, Devin talks about his mom all the time,
but I am nervous, of course.
- Hi, how are you? - I'm good.
This is like a first for me.
I really thought this was a catfish.
-No. -[Elaine] I told... I was like,
"Oh, my God. What if some guy pops up on the screen?"
And it's... I mean, what do I say?
I'm still in shock.
It's like your total opposite of what I expected.
What do you... What did you expect me like?
I don't know.
Not so much the innocent look.
[laughs]
I will tell you this.
I didn't grow up, um,
I don't know how to say this.
I know how to say it in Spanish
because my mom always says it to me. She's like...
[in Spanish]
And I wasn't born in a golden crib.
I have... All my life I've had to work.
Well, you should be really proud of yourself for that.
You seem to be a very pretty well together girl.
And it's just...
Do you know what you're getting into?
Like before,
uh, you know Devin got his time,
he probably wouldn't have been somebody
you would have spoke to.
- Mmm-hmm. - [Elaine] You know?
Because Devin was wild.
- [Isa] Yeah, he told me that. - You know, he's just...
But, like, I feel like our... My conversations
with Devin are very, like deep.
You know, he has a lot of goals.
He's very ambitious. I see.
And you know, he's always telling me
how like prison has changed him. You know?
I just don't want you to...
- [Isa] Get involved? - Get hurt.
Get wrapped up. And, you know,
people talk different when they're in jail.
And Devin is a sweet talker.
- [Elaine] Yeah, I know. - You know?
I know he's not an easy man.
I know people look at him at,
not easy, but he's such a mush. [laughs]
[Elaine] Look, he is.
He's a big, big teddy bear on the inside.
But, you know,
um, he's still gonna have to come home
and face reality.
You know, about things that have happened.
- [Isa] Mmm-hmm. - [Elaine] Which will be hard
for all of us all over again.
But, you know, we're here.
We're gonna be here for Devin, always.
For Elaine, I do sympathize with her a lot.
Devin first went to prison at age 14.
If I were in her shoes, I'd be crying too.
You know, I don't want my son in jail.
I don't want my son missing out on important holidays.
It must be really frustrating for her.
I'm so sorry, Elaine.
- That's okay. - If I could only give you a hug.
I'm... I really am sorry.
You know,
I don't know if that's something you think about, like,
but he's got a lot of proving to do,
you know, to everybody.
[Isa] I'm definitely worried about Devin falling back
into his old ways.
You know, I don't know what I'm gonna do
if he goes back to prison.
Look, I don't wanna do this whole thing again.
I would really, really love to help him.
You seem like you would.
Um, it's just a matter of...
if Devin wants... Really wants it.
[upbeat music playing]
Hmm.
So, I'm about to have a video visit with Manuel.
And we haven't talked in a few days.
I'm slightly worried that something's going on
with Manuel or maybe something's going on
at his prison. Maybe he's hurt.
I'm not... I'm not sure.
Um, because it's not like him to not respond.
I guess, we're gonna see if he shows up
because he's late. So...
[dramatic music playing]
[Chelsea] I'm starting to think
that Jonathan was right,
that I'm getting ghosted
and it feels really crappy,
I'm just a few minutes left, and then it'll be over.
But he's not showing up to the video visit,
it looks like.
I can't believe that Manuel stood me up.
You know, I haven't talked to him in a while.
And then I was really looking forward
to seeing his face and nothing.
- [Ashley] Hey, babe. - Hey, how are you?
- [Ashley speaking] - Good.
So something's happened.
[Ashley] What's wrong?
- Hmm? - Um,
I went to do my video visit with Manuel.
- [Ashley] Mmm-hmm. - And he never showed up.
[Ashley speaking]
Nothing.
[Ashley speaking]
Yeah, at first, I was worried.
But now I'm not worried
because I feel like
if something bad had happened,
I think that one of his friends
in there would've messaged me.
Now, I'm just kind of like, pissed.
[Ashley speaking]
He's in prison and needy.
[Ashley speaking]
I'm not real sure what to think.
I can't make plans to go get him
if he's not even talking to me.
I'm angry,
I'm sad, and I'm confused.
[Dexter] I told Brey I would think
about this whole prison dating thing
and I can't believe I'm really saying this
but maybe Brey is right.
Maybe I should get back out there.
I haven't dated in a really long time.
And the last few girlfriends,
they were disastrous.
Maybe dating an inmate
is, um, what I need to do.
So, that she can have
the opportunity to know me
and I can get the opportunity to know her,
no fancy dinners.
Maybe that's what I need.
An honest to goodness conversation
and someone getting to know me for me
and me getting to know them.
[upbeat music playing]
[Dexter] I'm meeting my best friend Charmaine.
-There it is. -Thank you. I appreciate that.
Yes, yes, I know.
Charmaine probably knows me
better than any other woman
other than my ex-wife.
She knows where my bodies are buried.
So, I'd really wanna get her take on the matchmaking.
Well, as you know,
I haven't had much luck,
you know, in the dating arena.
- Right. - [Dexter] Um, you're familiar
with my last relationship.
Indeed.
So, I decided to, um,
try something a little bit different.
Different like what?
[Dexter] Okay.
I enlisted the help of a matchmaker.
Oh, okay.
And, um, there's a little more to the story than...
Just spit it out, man.
- [Dexter] All right. - Spit it out.
[Dexter] All right, you my girl.
- Yeah, right. - [Dexter] So, we can talk about everything.
- Right. Everything. - [Dexter] Okay.
The matchmaker matches people
like me
with women from prison.
[Charmaine] Women from prison?
Yeah.
[laughing]
[Dexter] Why are you laughing?
You can't be serious.
Dexter is telling me that he's getting matched with a inmate.
I really... I really don't know
what to think at this point.
- Are you kidding me? - [Dexter] I'm dead serious.
Oh, my goodness. Y-ou know, you know,
I've tried everything else.
- Yeah. - It's not been working.
Come on, Dexter. But from prison though?
[Dexter] Yes, why not?
- What's the worst... - What you mean, why...
- What's the worst? - I know, you ain't just saying,
"What's the worst that can happen?"
- [Dexter] Mmm-hmm. - What you mean,
what's the worst that can happen?
- Hey. - You can be found in a trunk of a car,
you can be in the middle of an embezzlement scam,
you can be found on the back of a milk carton.
Like come on now. You know, I'm a little smarter than that.
-What do you mean smart? -[Dexter] Okay. I'm a little smart.
I know what to look for.
Based upon my last failed relationship.
My last relationship
I pretty much gave everything I had
but when my money was gone
and she was too.
And I've been rebuilding ever since.
I think that I've learned from the past,
my eyes are open
and I'm ready to try something different.
And you don't get any different than this.
[Charmaine] And what do you have in common with an inmate?
That's what I'm gonna find out.
I mean, it's not like I'm just saying,
all right, I'm gonna go ahead
and I'm gonna find somebody and this is it.
This is just a area that I haven't looked at before.
[Charmaine laughs] I can't believe you.
[Dexter] What's hard to believe about it?
What you mean what's hard to believe on that, Dex?
So, I'm not getting any younger.
[Charmaine] I understand that.
-And... -[Charmaine] I understand that.
I've been in this game a long time.
I feel like I've given
all the other ways a chance
and it just hasn't worked.
I think you're giving up on you.
I really think that this is a very bad idea.
You know, I knew Dexter's last girlfriend, you know,
and, um, I felt like he's being taken advantage of
because Dexter's a nice guy. You know,
he jumped into it.
And he gave his last penny,
you know, and she just left him high and dry.
I do not want that to happen to him again.
I mean, what is it with you?
This is the lowest right here.
[upbeat music playing]
[Olivia] Hmm,
are you read for a little nap?
[Chelsea] Hmm. I love it when you do my lashes.
- It's so relaxing. Yeah. - [Olivia] Yeah. Good.
It's been days and I still haven't heard from Manuel.
I've been feeling kind of down and depressed lately.
So, my friend Olivia's going to do
my lashes for me.
A little self-care
always makes a girl feel better.
I appreciate you coming.
Yeah, of course.
Got so much going on here lately.
[Olivia] I bet.
Oh, do you mind if I take this?
[Olivia] Go ahead.
[Chelsea] Hey, what's up?
Hey, babe. What you up to?
Um, my friend, Olivia, she's getting ready to do my lashes.
- Hello. - [Chelsea] Just say,
- hey back there. - [Ashley] Hello.
What's new?
[Ashley] Um...
So I did something.
- You all right? - [Ashley] And promise me
you won't get mad.
[laughs] That's always scary.
So I made an account, um,
for those like, you know, to write an inmate.
- Mmm-hmm. - [Ashley] Um, the ones
that you're telling me about.
And I decided to make a fake profile
to basically see if men will...
Would answer to the fake profile
that I made.
- And guess what? - [Chelsea] Okay.
[tense music playing]
[Chelsea speaking]
There's something about the bad boy in prison
that I am attracted to.
Oh, my God.
[woman] I just can't wait for him
to walk out of those doors.
- So, I'm Arlette. - [Brey] I never would've
thought in a million years I'd be talking to someone
in prison so cool like her.
- [man] Hello! Hello! - [woman screaming]
[woman] People think I'm crazy.
But Bryce is my soul mate.
[woman] I wouldn't fly to another state
to meet a complete stranger getting out of prison.
[Jonathan] You got something on your face,
it says stupid.
Do you know that's where you got in trouble.
Why would you even go back there?
And on top of that, you're drinking.
I did have a few beers. So I kind of lost track of time.
I just feel like you going back to like your old ways.
[Dexter] What would be the first thing
you would want to do when we meet?
I want to experience to go into a live NBA game.
- Right. - [woman] I'm sure
it's beautiful in New Orleans.
Sounds like money, money, money to me,
if you ask me, that's the sign of a gold digger.
You're about to graduate soon and he's about to get out
of prison like at what point do you say like,
I don't know if this is the right decision?
[woman] Me, and Bryce, and mom,
we've been having a merry-go-round.
Sometimes I feel like I'm fighting
for a spot in Bryce's life.
[Chelsea] He's disrespected me twice
in less than two weeks.
[woman] Our connection is super deep
because we've tooken the time
to get to know each other mentally and emotionally.
And he better not mess up our plans for the future.
These women are a little bit more dangerous than we know.
Don't let these curls fool you.
[woman speaking]
What?