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A Conversation With Jessica Hall

Radio and TV personality Jessica Hall sat down with Giddy's Marisa Sullivan for a discussion on the stigma she faced as a former Playboy model, the heartbreaking reality of miscarriage, and her eventual transition into motherhood.

Hall's association with Playboy has followed her throughout her life. The stigma and judgment of others has been difficult for her, but she ultimately doesn't have any regret about what she has done because her experiences have led her to where she is today: a wife and mother of two children.

Before giving birth to Sophie, 6, and Jake, 4, Hall had a miscarriage. This devastating experience left her blaming herself and searching for answers. Thankfully, after a year of trying to get pregnant, Hall and her husband, Kyle Carlson, gave birth to their first child.

The "Flashbacks" podcast cohost had growing pains when adjusting to life as a new mom. She hilariously learned about how her postpartum breasts can leak during a casting call for a potential new gig. Since that time, she has learned how to "train" her feedings and was able to successfully breastfeed her second child for two years.


Marisa Sullivan (MS):

You grew up doing Playboy, MTV, hanging out in Hollywood. How did your husband, Kyle, embrace this culture you were in?

Jessica Hall (JH):

He is from the Midwest. He didn't even live in L.A. at the time.

He was a little taken back by it. He was like, "Oh my gosh, what am I going to tell my family? You've posed naked for 'Playboy."' 

And I go, "Your family would care?" In my mind, since living in L.A. and being here since I was so young, it just felt so normal.

He doesn't judge by any means, but he was worried about how others would judge me. Even taking me home to Minnesota was hard because his family was like, "Who is this Playboy chick from LA taking our sweet, innocent Midwest son away?"

After meeting me, of course, everything worked out fine. But it was this stigma that I had. It was a mark against me because of what I had done.

And, do you know what the funny thing is? When I first posed for Playboy, I hadn't even had sex yet. I was a virgin. I took my clothes off before I had sex.

It wasn't fair. Like, I said, you have this big mark against you. People would think, "Oh, she must be easy, or hooking up with these guys, or she'll do this or that." But no, I won't.

Doing Playboy didn't define me. It didn't make me this free-for-all, confident person. It was hard.


Have you thought about how you will talk to your kids (Sophie, 6, and Jake, 4) about these topics?


I get this question a lot, and I have never been fully able to answer it. People will direct message me or ask me questions on Instagram. They are reverting to, "How are you going to tell your kids what you've done?" And I think, "Hopefully you are perfect before asking me this question."

A lot of people don't ask in a loving way or because they are interested, they are just prejudging.

First of all, there are so many things that have happened in the world since I've done Playboy—things with social media and women doing so much more—and Playboy's not really around anymore. Hef sadly passed a couple of years ago, and I don't even think my kids will know what Playboy is when they get to that age of asking me.

But I will, when they're at an appropriate age, let them know what I've done. I kinda laugh now because everything is so accepted nowadays that I think they'll be like, "Okay mom, cool."

To this day, I still get lots of fan mail from the Playboy followers with my Playboy pictures—and I don't look at them like, "Oh my gosh!" I look at them and think, "Damn, Jess. You looked good."

Now I'm a 38-year-old mom of two, and it's nice to know that I don't have any regret about it. Some of the photos take me back a little bit, but I also look at it like, "Wow! These are so beautifully done and I can't believe my body looked like that at one moment." After going through two children, my body is just so different.


And back to Kyle: He embraces your life and what you've done, and he has always been very secure. Let's talk about what you should do as a husband to have a healthy relationship where you can trust each other.


My first date with Kyle was coming off another date—I had double-booked myself for the night. I was 20 years old and I will never forget coming off the first date and going to the second date, which was Kyle, and sitting across from him in this sushi restaurant and thinking, "Mother F-er. I just met the guy I am going to marry."

I was 20 years old and I felt like I had the whole world at my hands, I had just done Playboy. But I knew right then and there.

We have open communication like no other. Sometimes it hurts, sometimes it doesn't. It's just like, "Alright. Let's figure this out."


Was it the way he carried himself? Why did you have that instant feeling about him?


I was the type that thought, "I'm not gonna get married until I'm 30," and I had this whole plan. But then, when I met him, that just went out the door.

I just knew. I can't explain it. I was a couple of months shy of turning 21, and he would tell me, "You're young. I don't want you to have any resentment when you're older. Go out, have fun with your friends, go work, do whatever. Obviously, respect me, but live it up."

We waited to have kids. We were married for a good seven years before we had our children. We really experienced every phase of life together. I was growing with him—and some people grow apart, but we didn't. He's four years older than me and it works. It works great. Out of everything I have ever done, my success story is our marriage and what we've built.


I know you had a tough time getting pregnant.


I had my first miscarriage with my first child in 2014. It took me so long to get pregnant, but I was pregnant and I went in at the 6- to -week mark and saw the heartbeat, everything looked great. But then I went back at the 3-month mark and everything just stopped. That was hard. It was my first time getting pregnant. I was so excited and that was just so heartbreaking.

It took a solid year to get pregnant after that. We were doing everything right, and I found myself falling into a little bit of a depression, thinking, "What did I do?" Everyone could tell me that it's not my fault, but I'm not listening to them. At that moment, I just thought, "It is my fault. It is."

My best friend, Kendra, and I had this whole thing at the time that we were going to get pregnant together—and we did. But she ended up actually having her baby and I didn't. She was so supportive. She is like my family. It has been 15 years. She has had such a rough time with her own family, that we have just become so close.

I remember at her baby shower that I threw, it was hard. When I finally was able to have my baby, Sophie, just the support that I had from her and my friends was just overwhelming. It helped, for sure.


So, for the women out there who have struggled with this, how did you finally get pregnant? Did you have to use IVF or was it natural and you were just patient?


It was natural. I was supposed to go in at the year mark to figure out what was going on and why I wasn't getting pregnant.

I remember going to this wedding a couple of weeks before that appointment, and I finally let loose because I knew I was going in to get it looked at—and I ended up getting pregnant at that wedding. It happened the second I let go. If I hadn't gotten pregnant then, I would have had to think of alternate routes at that appointment.


And I want to talk about your podcast, "Flashbacks." Here we are in 2021 and everyone's got a podcast. Can we talk about how great it is that we can control and own our content? How empowering is it for you, as a woman, to go on there and say whatever you want and tell these stories unashamed?


I feel empowered. I feel like people are listening—and if they don't want to listen, they can just turn it off. But just to have my own platform to talk about everything I've ever gone through—the good things to the bad things. There's been tears, there's been laughs, there's been drunk people on it. We've had people from all walks of life come on this radio show.

It's so cool to be in 2021 and have a platform. Anyone can have a podcast, so if you have something to say, you're being heard, and I think that's pretty awesome.

You know, now we embrace women of all body sizes, of all ages, of everything. People have spoken to me in the past about my weight, saying, "You don't look good enough," or "You're pudgy there," or literally even grabbing my flaws—what they thought were my flaws—right in front of me, in a casting or on an actual job. I know it is so cliché to say, but all of those things happened to lead me to exactly where I am today, and I'm not mad about it.

I just look at things so differently now. The things that I thought were so cool back in the day—like, "Oh my gosh mom, look! I'm on TMZ!" but I'm a drunken mess—why did I think that was cool?

Everything that I thought was so, so important in the moment, it really just wasn't.


What would you say today if you went into a casting and they treated you like they did in the past?


Can I tell you about my last casting? This was when I was like, "I'm never going back." I couldn't make this up.

It was this big casting and I was with this other playmate, Amanda Cerny—who is killing it now, she is so hysterical, I'm so proud of her.

But at this moment—it was five years ago—she and I walked into this casting with all these men and we had to do some funny skit. The waiting was so long. It was one of those castings where you sign in and keep thinking, "Oh my gosh, I have to go." I just had the baby and I kept thinking about how I had to get back.

I finally walked into the casting and it's really hot. I had this tank top and a little skirt on. It's been almost an hour since I was waiting in the waiting room. As I'm talking to them, they are whispering to each other, and I thought, "This is rude."

I told them, "I'm right here!" But then I realized that my boobs were leaking. Leaking. I had two big milk stains through my tank top. It was my first child, and I had been home all the time breastfeeding, so I was never leaking before because I always had her on me. With my second child, I could tell you everything, but not with this one.


How long do you leak for when you're breastfeeding?


Everyone's different. I was an over-producer with my daughter. I produced so much. With my second, I was kind of able to time it out and hold it back. You can kind of train your feedings.

Jake breastfed for two years. That kid did not get off me for two years. But, I have to be honest, I lost so much weight—my weight was just coming off with the breastfeeding. So, the second I quit breastfeeding, I gained 12 pounds right away. So there was a definite plus to breastfeeding.

Sophie quit me after 8 months, but then I pumped through a year.

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