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Nostalgia & Now

Kelli Williams

Self-Assurance and Advocating for Value

From 169. Devyn Simone on The Challenge, Matchmaking, & More!Jul 6, 2026

Excerpt from Nostalgia & Now

169. Devyn Simone on The Challenge, Matchmaking, & More!Jul 6, 2026 — starts at 0:00

Still waiting in line? Aain, That's time you'll never get back. Save time and money with stamps dot comot Over four million businesses have skipped the line with stamps dot comot Join them to save up to ninety percent off carrier rates from your computer or phone right now. Print postage for certified mail, registered mail, and packages in seconds. Then schedule a pickup right from your home or office For a limited time, go to stamps dot com and use code podcast for a free welcome gift. Tasses and fees apply. Everyone treats summer like it owes you happiness, L days, pool parties, your best life on a loop. So what does it mean when you feel worse? The summer blues are real. It's why summer is one of the busiest stretches of the year for people starting therapy Grow Therapy is here for all the moments when you decide you want more, more support, more clarity, more tools Gro connects you with thousands of high quality licensed therapists across the US, offering both virtual and in person sessions, nights and weekends. The therapist you want takes your insurance on G. Gro accepts over one hundred twenty five insurance plans. Sessions average twenty one dollars with insurance and some pay as little as zero dollars depending on their plan Visit growtherraapy. com slash start now today to get started. That's growthapy. com slash start now P. com slash start now Availability and coverage vary by state and insurance plans Why does the same news story sound completely different depending on where you read it That confusion is exactly what Ground News was built to solve. It's an app and website that compares news coverage, allowing you to see how each story is framed across the political spectrum and the world. For the recent story about the US signing the memorandum of understanding with Iran, their vantage plan shows us that, Right Leaning Daily Express framed it as a historic peace deal, while lefte Leaning NPR notes it resulted in the president's approval hitting record lows plus data like each publication source of funding and a factuality rating. The Nobel Peace Center even called Ground News an excellent way to stay informed. avoid echo chambers, and expand your worldview. Get forty percent off by going to ground. news slash twenty twenty six. That's ground. newews slash twenty twenty six Ground. Ns slash twenty twenty six. You guys, welcome to another episode in Nostalgia. Now, as always, it's me, Kelly Williams. and this week, I am joined by a challenge finalist, a host, a matchmaker. and now she's heading into the Bravo universe, Devin Simone. Thank you so much for coming on the podcast Yeah, thanks for having me, Kelly. Hi. Hi. It's so nice to virtually meet you. I've been watching you on my TV for many years now. Well, thank you for having me. I'm glad that we could make this happen. I'm excited. and forgive me because is a Monday morning and I don't know I was trying a new coffee order yesterday. I'm getting into my coffee And I saw one on TikTok and I feel like I don't know, whatever they had me doing, I woke up feeling hungover this morning, which is weird because it's coffee and there's no alcohol, but I'm definitely I don't know Yeah It's okay. It's okay. G it. It is a Monday. You were just experiencing the World Cup, which I can imagine took a lot of energy out of you. That was fun. That was so fun. It's like community, a vibe Go with your friend. Also if you're single, I mean, it's a good place to Jink to meet people, you should go. But yeah, it was a good time Well, awesome. and before we get into your MTV life and joining Ronie and everything else, I wanted to start with somewhere like a little different because I know you're remembered for the Whig funeral. and we will talk about the Wig funeral.amira. But watching you on free agents Final is one of my favorite challenge moments of all time. and I remember actually getting emotional justust listening to you hype yourself up as you finish that final What was that experience like for you? and how do you look back on it now You know, it's funny I haven't watched it in a little while now, but even a couple of years ago when I watched it, I actually would still cry when I see that because it's One of the gifts the challenge gives you is the ability to hold on sorry, my dog. Oh, it's a toy. okay. He's like roaming around here and there's like Beauty, ex a beay stream. there's like stuff on the floor you never quite know what he's getting into But the gift or the challenge is you get to watch these really intimate moments where it's like I was truly in fight or flight mode in that moment, especially when I'm on the bike and I'm like saying to myself, like I wasn't aware it sort of a And yeah, I feel like for the little girl and me, for all the like young versions of us when they're hard moments and you aren't sure you can do it or you're doubting yourself or you feel like it's just super hard watching that was just Yet living it was know insane and watching it back is really special too. And Yeah like it's crazy that it's been so long ago, but it really would, I mean that is That's what I lo about the channel. It's like's part it's raw That's real, right? Like that's not scripted, that is very much in the moment at your Rwself D that change the way you looked at yourself finishing that final? Do free agents as a whole, yeah, a hundred percent changed the way that I looked at myself because the whole time I was there, I thought, a, I'd never make it the in. and B, I was like, you know what? let me while I'm here and like hanging out in this beautiful environment with these crazy but like entertaining and fun people and creating these stories Why don't I try to be a help for some of the other people here? So I do think part of the reason I didn't get voted out that was a lay upp. But also because I had really great conversations with so many people in that house, like one on ones about their love lifeves or about whatever was going on back home. And so for me, I was like, you know what? let me be just like a piece of sanity. and then that's kind of my like I would like pray about it. like elimination. That's sort of my like deal. I was like, hey God, look, I promise that'll be helpful. If you let me stay another week. But then Towards the end I was like, well, I've talked to everyone here probably not really helpful anymore. I'm for sure going home. And then I end up in the final and finish the final. then I realize know that song wake me up when it's all over. and it's like all the time I was finding myself when I didn't know I was lost. and to me, that is the epitome of that season. one because it came out around that time, but two. It's like, yeah, I didn't realize I needed that final. I needed the like motivation and the proof that I can literally do anything if you do it just a step at a time. Honestly, I need to remember that as I clean my house now because it's a mess. And there you just look around and you're like, o, there's so much stuff. I can't, I don't know where to start. I'm probably going go back and rewash that fino. like, girl, look, if you can do that, you can clean your home office. but it was really special. It's such a gift. And one that bnds you, I hung out with Laurel recently. wee ago And she wass in New York and we hadn't got to spend time together in years And she was talking about just that final and the three of us there and I felt it was who was supposed to be on the mountain at that time Definitely what is it like reuniting with your challenged castmates after not seeing them for a few years? Do you pick upp where you left off or is it new? Just really good question. It's a mix of both. So like on one hand, and she posted like a snippet of it to her Instagram recently, it is like a pickup where you left off in a way, but then it's also wholly different. Like Laurel is doctor Laurel now you know. But at our core, I feel like that safety and trust is there and I don't not explain it, but it's like we went through something, you know, and like So there's like this element of unspoken trust, att least that's how I feel with so many of my castmates is how I fell to the reunion, being back in a spe with so many people not only I done a show with but that I roomed with. I roomed with Leoy and CP and bananas at a point. And then I've seen some of them outside like, you know, Derek Kay has met my husband. and so it was so interesting and cool to like see them you know, again, when we've bothoth grown so much And then some of us have evolved and some of us Less so. but still Well, I guess let's rewind a little bit because none of this would have happened without real worldor Brooklyn made you want to audition for the show Funny enough, look, you know, his ego is a healthy size. So I don't like to contribute to it But Bananas was part of the reason. And Noxs ever watched the challenge or because I' ever watched real world either. but my then colleague's boyfriend with a club promoter, donon't takeate club prers. And He flew in Bananas and Kelly An to host a New Year's Eve party. I think there may be pictures of it somewhere deep in my Instagram. And Because I was an impeccable girlfriend and supporter, I was sort of like she' a right hand woman or like assistant or logistics manager. So I would to pick up Bananas and Kellyanne from the airport. and I knowew who they were because I watched real world growing up, but kind of had stopped by the time I hit college And then I just remember There was this magneticism with bananas in particular. like Kelly Anne was stunning and is stunning. The girl hasn't aed at all. But bananas just the way people reacted to him and this confidence he had. And I was driving along my little purple volkswagen beetle with the Winnie the Poop steering wheel cover and him in this front seat, and I think Kelly's in the back and I'm in like some mini dress, beaded mini dress or whatever for this seers party. And we stopped at McDonald' And I got some chicken nuggets, I think, and an ice cream cone because their ice cream machine was working that day. And I remember I was to make a left turn and I'm holding the ice cream cone in my right hand Now when I turn around, I realize there's a big ass bite taken out of my ice cream cone. and it's because this man who I've known for all of two and a half minutes, has just taken a bite out of my ice cream cone while I'm holding it, and he's sitting there laughing I annoyed because I don't know where your map has been also like respected it a little. And then as the night went on, I just remember thinking And Kellia was stunning, but I kind of thought like if they can do it, then damn I can do it. And I literally went home that next day And this is before laptops had built in cameras. I know, God, sounds old. And so I like went to Walmart and bought camera, I fully planed return to plug in and record my like initial because this is the first year they allowed you to submit. Like when I Googled it, it just so happened to be this is the first year you could submit without going to an in person casting. Okay. So I was on the only person on my season that didn't go to an in person casting. I see a little video. h actually like I like probably made sixth versions of that video, went to sleep woke up and was like, no, actually I need to make another version, made it, sent it. and then six months later I was on the very next season of Real Wor. So if I hadn't met Banana, he never we never talked about the show, but I feel like if I hadn't met him, I probably never would have even considered it as like possibility or something? I don't know. And then you know we wouldn't be here and we wouldn't have Samera Oh, well, thank God we have Tamara and Devin Simone, to be clear Looking back on your season, it was an important season of the real world. I think Brooklyn maybe kind of gets forgotten in the mix somehow, where you had the first trans person. you had someone dealing with PTSD yet Chat has a, you know, You're so funny So funny What do you think people might misunderstand about your season? or even how you were portrayed, maybe You know, they portrayed me at Boy Crazy, which like everybody, they want to put everyone in the archetype, whatever. look Was I interested in the men's? Yet. And I never denied that, hence I'm a matchmaker now. But it was always for che and change like they tried to make it look like I was in love with my roommate Scott for like the whole season. That was not true. I thought he was cute for like the first three days. And then you know, sometimes you get to know people and know shade did Scott, but you just realize like, ye know, this is not actually like their better as a friend. And Scott was a lovely friend drrug it out in the show to make it look like I was pining over him for weeks and weeks and like that's not. I with him most of the seasons sure. But I wasn't pining over him. I actually became friends like at the time became good friends with one of the women who was friends with the girl he had started dating while on the show. L he met someone out And she would come over with her friend and I ended up becoming really good friends. and we were friends for years after that with friend of the girl. So anyway, I think that was a misportrayal And then the other part isn't on production like their fault, it was just mine. I wasn't that far out of like doing pageants and stuff where you're taught to be poised as you can be and like just and to be mindful of what everyone else thinks of you And so I went into that season doing that way too much. And so there were times that I didn't say things or I was thinking things or chose not to react do anything wild which I didn't. But on the other hand, I learned that if you don't tell your story, production will be incentivized to tell it for you. and they will edit it to make it look and say however you want.. And I didn't like that. So from then on I said, no matter what I do, I'm just gonna to be a thousand percent You know, like I'm not going kind of hold back because it's not that I wasn't being real, I just was holding back a lot The voite printing throughs got mad at me a couple of times for that. And so yeah, on the challenge when I look at the challenges now and all the other shows I've done, Love at First Wife, Max Be in Miami, any shows I may be doing in the future, even though editing can still change and manipulate things and has still feel at my core crd because I feel like Yeah, no, that's me. And if you watch me all these years or, you know, you get to see me on things like Windy show or today show where that isn't edited, like it's live. And it's like, oh that tracks that's her. And so yeah Well, that's awesome. It's awesome that you learned how to like be yourself on screen. That's really important. And obviously shown through during your time in the challenge Yeah. like it it was I don't even know if' so much to learn as much as For some people it is, but as much as just like a choice that like Look, you're going to offend because as much as I tried not to offend people in like whatever way. I just remember I'd get backlashed. for anything. like I could be brushing my hair and they'll be like, Ohh, she's so vain. And then somebody else would be like, why doesn't you do that, you know, do her makeup more? Like you're just somebody's gonna have something to say. And this is when social media wasn't as much of a thing. so it's definitely worse now. And it's not just like, look You get what you get, You like it or you don't like it, but it's a very like core of it, you'll never be able to say I wasn't real because I'm really me and it's consistent Well, what has that been like the journey with social media alongside you being on television? Are you kind of glad that you started before the influen era or Kelly. becausecause look at all these brand deals people are getting with one hundred thousand five early in my Re, come on, Zuckerberg things that are going to be more challenging living your life out loud on TV, but Even though I've started before that, I mean, I've still 've done things know, I've obviously still maintained some sort of a career on television to an degree. So I'm not without criticism or being sort of talked about online. but I didn't necessarily gets the benefit of like the following per se, because people aren't following people on the Today Sh like that. They're not following people on Wendy showhow. But I've built very loyal community from Wendy followers that I've seen Appreciate all of you. Yeah. so no, would it have been nice to get that little bump, sure But everything happens for a reason. and I think every season I was on was meant to be, every cast member I worked with was like meant to happen and every experience I've had, I don't take for granted because I believe it was such a gift That's a great way to look at it for sure. And I know you mentioned your matchmaking. When did you realize you wanted to be a professional matchmaker and how did you like discover that you were good at it I mean, never did I realize I would be impressed I tri, but I have always loved the psychology of relationships. alwaysways. like even as a kid There may be a clip of it. If someone ever digs it up, In my real world house, I was reading relationship books and they hated that because' boring to watch. But like I'd be in bed reading relationship books I as a kid would read relationship and self help books always been and still is very fascinating to me and how we connect, how we relate, what makes healthy relationships and not And then when I was in my twenties,, And even probably in high school, I dated a lot because I was also curious to bl I do believe you can kind of design your life and the partner you choose. And so I was curious in what that looked like, you know. Yeah, it evolved into matchmaking largely because I was coaching people I had a show I co created, co hosted with my dear friend Clinton Kelly, who was on What Not to Wear. He and Safy London actually have a show out now. I don't remember it but go find him on Instagram, and he'll tell you, but he's one, I loveon But we did a show about matchmaking people he would make over people's clothing style, I would make over their dating profile. So yeah, that was always just fascinating. eventually that turned into matchmaking. And now because I'm so busy, I've kind of stepp back from actively matchmaking. likeike I still the team that I was working with for all those years still connected to I still be coaching. and my goal is to because there's only one of me to replicate some of my tips and the support that I've given my clients so that it's more accessible like financially, but also just more accessible worldwide so that people can have sort of like almost like me in their back pocket. like when you're wondering, what do I text her back or what I text him? or how do I get off the apps How do I initiate this data? How do I express my needs or my boundaries? or is this normal? Am I overthinking all of that? I do want to put it in a place where people feel like they have me as a friend and have access to information and So help me God in my ADHD, we're working on that to get it to where people will be able to go to my website and download that and access it That's exciting. People will stop sending chat GBT messages. They'll send Devin Simon to God. Yeah, Yes. Kelly's like, please for the love of God, stop sending chat. And chat GBT isn't always the worst, but it is if you don't use it properly. It's just like a car maybe, I don' know, car's not always the worst car can be great for a lot of things. But if you don't know how to drive, it' That's not great. That's a good point. So I have my fiance. I amm very lucky. It was before the chat GBT text messages, but some of my friends will send me screenshots and I'm like, No, that isn't a human. that is AI. Yeah. Oh yeah. o yeah. yeah, it's wild. So this is gonna and even that, there'll be tips on how to like decipher those things, sort of benchmarks for how you can like not lose yourself in progressing a courts shit or dating, meaning like I always say, get on a phone call first. Wh even waste the time of a good shower and some good sunscreen. If within thirty seconds of hearing their voice and talking to them, you're like, oh God, why am I here phone call first, or don't make a phone call the date, all the things. I've got so much, I've been fortunate to have interviewed thousand of people. I'm now Tinder's resident relationship expert for the last three years and running. so I've access notot only to my own opinions, but data surrounding how relationships work and pairings and matches and all of that stuff. becausecause you know, believe it or not, they've made millions of matches and relationships and like the amount of success stories and invitations they get. It's just a really beautiful thing. So like putting all of that in a place where people can access it is certainly the goal Do you think being on television also helped you with this, especially when you're on the challenge of the real world with so many different types of people? Do you think that's kind of helped you at all with understanding people in general I mean, I definitely think it in a way when it comes to dating, I dated a lot. so I mean, I feel like that. I d it a lot and I read a lot. and then there's a lot of studies. But certainly my experience with such a wide variety of people, I also do feel like people on the challenge and largely reality TV in general, especially people who continuously do it Still waiting in line Again That's time you will never get back. Save time and money with stamps dot comot Over four million businesses have skipped the line with stamps dot com. Join them to save up to ninety percent of carrier rates from your computer or phone right now posted for certified mail, registered mail, and packages in seconds. thenen schedule a pickup right from your home or office. For a limited time, go to stamps. com and use code podcast for a free welcome gift Tax is a. Everyone treats summer like it owes you happiness, long days, pool parties, your best life on a loop. So what does it mean when you feel worse? The summer blues are real. It's why summer is one of the busiest stretches of the year for people starting therapy. Grow Thrapy is here for all the moments when you decide you want more more support, more clarity, more tools Gro connects you with thousands of high quality licensed therapists across the US, offering both virtual and in person sessions, nights and weekends. The therapist you want takes your insurance on G. Gro accepts over one hundred twenty five insurance plans. Sessions average twenty one dollars with insurance and some pay as little as zero dollars depending on their plan Visit growtherraapy. com slash start now today to get started. That's growthapy. com slash start now. P. com slash start now Availability and coverage vary by state and insurance pl They are a different breed. like they're not normal. but I say that in the sense that that's why they're entertaining to watch. You know what I mean? Like that's why We root for them, we get mad at them, because they're less like the people you meet in the wild, especially when they do it for an extended period of time Yeah. I would agree. And I think you can see that if people are on a show for too long. It's like, please take a break. Yeah, they lose their mind, It's just a sinch. whichich I think you had asked about like what it's like reconnecting with old challengers. And I do think that's one of the biggest things I've had to And is like, I'm a loyal it And someone who also is like object permanence, but that's not exactly the right way to describe it. But sort of it's like, okay, I remember the experience we had ten years ago. And if we ha't had a ton of experiences then, I'm still holding you to that experience we had ten years ago, right? You know withith room for a little growth, but I'm like, no, this person's loyal. They were great. We may not be so great now, you know what I mean? Like if you've been doing the show still or certain things that have happened since you may not quite be the person I remembered working with. So it's just holding space for both, right, whichich is like, I remembember this great thing about this person. I remember this experience of chared I also can say I've watched them or I'm watching them now in this season and how they're handling this And I don't love it. you know, or it's different than the person that I knew. Definitely, definitely. So Just back to matchmaking really quick, has that changed like how you think about relationships, not only romantic but friendships and even like relationships with yourself aking changed it as much as it's all just like in a big pot of stew. And I don't really love stew that much, But meaning like all of these ingredients, it's not so much that one came and completely shifted or changed I think I got into matchmaking because of the core of who I am. I think I got into the challenge because of the core of who I am. I think I was on a real world because of the core of who I am. So it's all of these different things that just kind of come out and make this meal or make this thing because of who I am and they all shape a little bit but at the core, I think it I've been incredibly fortunate to have built a career and lived a life largely driven by pursuing that which brings me joy. And it doesn't mean that there aren't hard things, moments that you kind of regret and scratch your head. likeike I was supposed to be on the challenge years before I ever was In hindsight, I think it was perfect and I came exactly what I needed to be, but I had turned it down know initially after my real world season. And I think it all just contributes to kind of who I am and I think who I am contributes to the work that I do or how I show up in all of those places.. So you've seen dating evolve from meeting people through friends, meeting people through apps, Do you think dating is actually harder today or are we just more vocal about how hard it is That's a really good question. I love the way you've phrased that Hold on, let me sit with it for a second. Yeah, of course thing dating is actually better today But I think it does require there is a little more pressure to be intentional about it And we are in fact more vocal about it. There's a community. so that like ups the anntte even more. But here's why I say it's better You know, there's psychological or like scientific terms for a lot of these things, and I don't remember them because I to say them. But one is sort of the way we romanticize the past even if it wasn't so great. And so when people are like, oh, my grandparents' relationships, or oh relationships back in the day, like sure some of our grandparents had beautiful relationships, right? Like A absolutely beautiful But a lot of our grandparents had relationships that were, particularly for the women of necessity rather than just choice. like in O parents lifetimees, there was a moment in which some states women still couldn't open bank accounts without men, you know, or where women couldn't like necessarily initiate the divorce. Like there were a lot of things where they maybe settled on the partner who lived down the street or that their family knew or went to the same place of worship because they needed to partner up, they'd be the odd man out. it was just easier. Now didid love grow from that? Sure. You know what I mean? was their appreciation But did they feel like it was a partnership? Did they feel they could fully grow to be their best self? Did they feel seen and loved and protected? Not necessarily you have the ability to A know yourself more, right? There's so many tools available to us. But then in knowing that to not just settle for the person you met at university, but to meet the person who, like I saw today, I sending to my dad and my brother them both because it came up in my Instagram feed that there was recently a bald and beautiful meetup here in New York City. and it was just like a bunch of bald people doing activities in the park So I sent it to them and someone in the comments said put, o, I wish I'd known about that. I love a bald man. But like just even there's so many opportunities to connect where you can connect with someone because you actually have a shared vision and shared values, whether that's a sense of adventure. and it doesn't matter if they live near you. You know My husband's from Australia. He lived in the States and lived in New York. But honestly, we would have never met without the app and what's crazy is we at one point worked across the street from each other. We used to go to the same dee in De Luca and still never met. Like even though we were in crossing paths that way, our exes went to college together and were're friends, still in friends Film never met. And so think The apps can be frustrating. I don't think it should be your only source of meeting people, but I do think it's opened up a world of opportunity where if you look closely now, the relationships that are going on in thriving, I think you'll find M diversity and more people genuinely happy both men and women, you know, anyone, anyone genuinely happy about the partnership that they chose. They're just not necessarily the loudest ones online. So it's easy to see kind of like those who are feeling frustrated, which is valid and those who are tired, which is all valid, All of those feelings are valid But you'd be surprised how many people are genuinely with their person. And also Harvard wrote about a study recently in their review and they spoke about it's sort of this ongoing study But that science shows us that the quality of life, both in animals and humans is in fact better when you have the relationship surrounding you. Now it doesn't mean everyone needs to be coupled up and that your life is terrible. It includes friendships. It includes family, but just in general, the idea of going it alone and I need no one and I don't need to be seen or loved or feel safe, it's just not real life at least for like there's an exception to every rule. but for most, it is not real life and there's science that supports that. So I love that now we have a bigger community. and I think bring it back to the World Cup. That's something, I don't know if you've seen the Norwegians doing their like that the rowing I think. Like the way community is coming together. People have described it as like a sleepover like in the US or like a thing where maybe the parents are feuding, but the kids get together anyway. and you're like, wait, this is great. Like this is so fun. It's like, yes, this is humanity, this is what it's about and this is like the beauty that's there. So dating that was a long ass answer to say, yes, dating is hard. It was hard then. it's hard now. It's a different kind of hard Prom you stay stead back a little clarity, then it's well worth it when you get on the other side Well, I love that you mentioned romanticizing the past because I feel like we're doing that with like pop culture right now as well, how there's no new sounds and nothing's new anymore because everything's being taken. And yeah, I think that, you know, I'm alost thirty five and I'm like, o, it was so much better when I was fifteen. Yeah, like truly, but it's funny because there were songs then that to us sounded original, but I know mom complain and be like, that was the clip of this song or that. And she did a great job of playing like then Oies, which by the way, our music is like now played on the Oie stage. What is this G? What do you mean? I know here O music is on the Oies page. Anyway, I dig. But like she'd be like, oh, that's a clip of this and and to us, then we didn't know because we hadn't heard the originals. and now we know the originals and we're like, is that Ls from back that A that they're playing in the wait a minute now. And yeah, it's wild, but you know circle. I do think though, some music has changed because they're writing it for TikTok. likeike they said that there's a formula now. and I do think I missed the power ballad. I miss the storytelling of a song. I think country music still does that a little, but they've actually evolved a little less. so they kind of have their same. But I do miss that when it comes to pop and R and B and the bridge. You know, I miss a good Christina yelling actually in a bridge. like I do feel like We need some of that. I mean, this is totally off topic, but what's like a good power ballot that gets you going? because for me, it's like all coming back to me by solution That good one When that I mean that. It's like I'm at the club in my kitchen. I love it. There's so many. I saw a clip and I'm sad that I missed it, but Deborah Kosts was on TikTok live recently and she was kind of singing along to how did you get here And she was singing along, we can't be friends and both of out. like we can't be friends I mean, it's a full story, right? It's like you went to my mama's house, you still talk, I saw your car. What are you doing? We can't be friends because I'm still in love with you and you she means it and you feel And then how did you get here? It's like bitch, I'm done dating. A lot of people can probably still relate then. I'm done dating. You're not supposed to be here. I tried the love thing for the last time My heart said no I mean, just They don't, you know, now days is blank I was walking down the street. And like that's a bop for when you're walking down the street, but sometimes you just M I agree. I agree. I miss storytelling. Even the call by backstreet boys, storytellers. Yeah with Brittanyy Justin now we've learned a lot of things about Justin since, but we cr and we felt it So I have waited long enough. I do have to talk about the greatest moment in challenge history, which is the Wig funeral. How did you come up with that idea? Literally was not planned. Like it literally there is no You know, I'm good when it comes to dating. like I can give you a strategy, but in everything else in life, it really just is a the things I do or say or noises that come out of my mouth. fully happening until it's like already kind of All I remember is that I took off that wig because I saw the challenge was that sand rolling the thing and I was like, oh, this is going to be disgusting I think I left it on even. Yeah, I left it on. And then when I was done, I took it off and we lined back up. So I was like, it's got sand and like how I'm not gonna to wash this Like what are we doing? And I'm to take it off. and then I wasn't just gonna leave it in the desert. Like I didn't really know what to do with it. I think I maybe even ask producers like where do I put like what So I think I put it in like a There was like a bag around and I like put it in a bag and took it with me on the bus and didk home. And then we got to the house I don't even know what started it. I honestly, I was delirious and I think probably I was like, I'm gonna haveving funal for becausecause I hadn' named them. mainly so I could keep track of them. Like she'd already been named Tia at Mare and I had another one. and I can't forget her name. I feel bad. Oh well. She was wavy though No, that was the straight one. The straight one. I can't remember her name. I like the straight. But I was just like God, I'm having funeral and then everybody got on board. and I don't even know how they got on board. And I also don't know like Bananas and sea, you're going to be the pall bearerars of my wig. In hindsight, I do think that's a little iconic that like these great We're carrying my wig in an open casket. to the beach for a funeral. not no one else can say that they managed to get those men to do that. And Leoy be the pastor and Anisa to sing, you know, I really don't know, but it was a moment of us coming together. Yeah, R and P she died for a good cause She did because the challenge doesn't have silly moments like that very often anymore. So it is like a very special time of that show. And I mean, did you ever expect people to bring it up years and years later sure it was going to fully make it. I think it was maybe a couple weeks before it aired that I heard from like a producer that it had made the cut because of course, we film so much stuff. and a lot of times You know, parties or things we do won't necessarily make it. And yeah, I did not expect that all these years later, it would still be a thing. And I love that it connects so many of us. Like I love that people still come up and be like, are I pizera or like like I just I love it so so much. I still remember the day I went and bought her and like never in my life when I was at the beauty supply store of my friend Marquel, did I ever think, ooh, this is going to be a moment. which which is if I had to give a b, not that you ask, but about reality TV now My gripe is that sometimes and I know Like, I'd like, well, I used to think this about my cast on in my real world season, although later I found out Hollly true. But like truly, when I went on real world There actually wasn't a hidden agenda time from getting a bigger platform, right? Like I didn't go in be like I'm gonna be this, I'm gonna do this, I'm gonna say this. I'm Wait. I did actually go in saying, I'm never going to look un putut together on camera. And then within the first two days, I had proactive in my faace and my hair and rollers sing in the basement. So that went to hell real bad. But other than that, like there was no pre conive anything. And I do think now in reality shows, it's annoying sometimes when you can tell people come in from the jump being like, I'm gonna do this or when I hear people being like, o, I studied and watched or I went I mean, it's not bad. It just makes me a little like because feel like what's so great are these authentic ality. You know what I mean? Like at the time, But An I didn't plan to eat my ice cream cone when we were in the car. That was just who eat. like that was just And he probably didn't even really remember that. like because he was just it was like nothing. So like, I guess that's I don't even remember that wasn't the question, but yeah, no plans. and I never thought it'd be so big. And then Here we are coming years later. Yeah. And one thing I really admire about your career is that you didn't just stay on reality TV. you kind of built a career completely around that kind of before people were doing that, honestly. And you've hosted the aftermath, reunions, the Challenge official podcast, you've done the launch specials, was hosting something you've always been passionate about or Did MTV like present that idea and And you were like, yeah, I'll do it. Oh, MTV didn't present anything. Lord. I mean, I used to host a radio show in high school, which most people don't know And not like a high schoolool radio show. It was broadcast in the T State area, but it was called Generation of Rap. So it was four teens. and I became actual moderator because it used to be that it would have like an adult as a moderator and then teens as kind of like the cohost And then I eventually I did it for about three years and worked my way up being the first like moderator where I ran the whole show. and so I liked that, but I always thought I'd be in acting. I went to school for theater music. Most people don't know that. And so I actually had swear I'd never do reality TV because I was like, o, I'm an act. like, ow, I'd never do reality whichich is wild. So that's why I say never, say never. And on my season, Chet was really the one focusing on being a host. I actually was auditioning to be on Broadway at the time And then afterwards, how did it I don't know where the pivot came. I think it's that my natural energy li having done the radio stuff. Oh, I would also host back in Kansas City like. talent shows, I hosted I would do the MC for Pageant. So it just kind of I had this natural would get asked for these gigs. and then eventually, it took many years But I recognize have a skill in this. Like I like it, but also like look, I like singing will never be Whitney Hgh. Like there are some people who can wake up and hit a note that just make your whole body tingle in a second warm up a lot, stretch my vocal chords a lot and then I can get a couple notes are not bad. going to be no matter how much I love it, just it's not it's not going to be For me, hosting and there's a lot that goes into it. So sometimes when people are like, oh, they should have so and so hosting. I don't think people realize Particularly if you'reking about something live, you have someone talking, imagine someone having a full blown conversation whispering in your ear while you're reading something, making it look like you're not reading that thing, asking questions to people, but also having to say aware if their answer something you didn't expect because now you got to pivot and answer, but you still got someone talking to There is a million things going on that most people, I think would struggle because it's not normal. L it's not normal to have seventy five things coming at you and you just still just look like like nothing. But really, that is what's happening. And so I realizeed I should say I'm the Devon Booker of that. And it's taken a long time to say that meaning I always when I would get booked for things, like I do appreciate the team who used to work on integrations with MTV because they're the ones who kind of unlocked a new level when they did the universal MV Universal studios MTV challenges, and they called me to basically be TJ. And I didn't audition for that. they just called me to do it. And then we did it for five seasons. The last one is the mysterious unaired season because of COVID, which was the wildest season of them all. But yeah, I just finally realized it was actually after the aftermath and we were doing a live when we did the live launch special And there was a lot of things that weren't fully done with that where I actually helped produce some of the questions and the flow. and there were some technical difficulties going on. But when you watch it, I don't feel like you can tell just how much chaos was going on behind the scenes. And at the end of that, even some of the producers came to in they're like, oh my God We couldn't have done this without you, L this wouldn't have I was like, oh, no This is my superpower, like this is my special skill. And then I've been fortunate to learn and work with so many great. So working with Wendy was a dream. and I'd forgot. I talked it apparently the challenge house. Nonie reminded me recently. Apparently I used to say have a challenge house of my dream to you know, meet Wendy and so have having gotten to work and sort of learn from her, you know, Sherry's wonderful host, Hoda, Cotbe amazingly, incredibly kind and learn from her, Jinna Bush Hager as well so many people that I've gotten to work with see how they do it with such grace and just try and take all that and me and put it into one. So no hosting wasn't always a thing, but I finally stopped My mom is when the kid said she saw me hosting and I was like, Mommy wrong. S was like she saw living inew York and I was like, mom, you're Jokes on me. I li in N York and now I host But yes, I'm the Devin Booker mayaybe even Some days to Michael Jordan of hosting, I would say Michael Jordan But I love it. I appreciate it. And I'm always trying to learn and grow and And there's such amazing people to learn from. Obviously Oprah was my number one inspo from the jump because the way she does it is also effortless. but yeah Now that you've done the Challenge podcast, being on the other side of these conversations, has it changed the way that you look back on your reality TV experience at all? Still waiting in line Again That's time you'll never get back Save time and money with stamps dot comot Over four million businesses have skipped the line with stamps dot comot Join them to save up to ninety percent off carrier rates from your computer or phone right now. Print postage for certified mail, registered mail, and packages in seconds, then schedule a pickup right from your home or office. For a limited time, go to stamps dot com and use code podcast for a free welcome gift Taxes and fees a lot. Everyone treats summer like it owes you happiness, long days, pool parties, your best life on a loop. So what does it mean when you feel worse? The summer blues are real. It's why summer is one of the busiest stretches of the year for people starting therapy. Grow therapapy is here for all the moments when you decide you want more M support, more clarity, more tools Gro connects you with thousands of high quality licensed therapists across the US, offering both virtual and in person sessions, nights and weekends. The therapist you want takes your insurance on G. Gro accepts over one hundred twenty five insurance plans. Sessions average twenty one dollars with insurance and some pay as little as zero dollars depending on their plan Visit growtherraapy. com slash start now today to get started. That's growthapy. com slash start now. growthapy. com slash start now Availability and coverage vary by state and insurance plans Kelly an awward because she ask really good questions. Thank you. If there's some voting, send me the link. I will vote. Yes,. Has it made me look back differently but it has It helped me flex my muscles of really extending grth because It was so nuanced because on one hand You know, and I would tell people this when they would criticize us online, which look, all feedback is appreciated because it's Chatter and it was helping podcasts. But like I'm paid for my opinion, right? So it wasn't like doing a proper news story where I'm supposed to be neutral. Like Daveon and I and Tori and Anisa, like we were paid to have an opinion about the episode. But then we would have guesss on. and it may not align with our opinion. And I always wanted to be conscientious of making sure they have the face to feel like they could express their POV from the house because ultimately, we weren't living that exact moment. And so it is a delicate dance to be authentic and stand behind your paine. And there were some guests who came on and challenged us in those and we appreciated it, but also for our guests to feel safe and to ask the questions also that we felt like the fan that I don't even like calling them fans. It's like I think you guys as the extended Challenge family really, but just that the supporters wanted to know. So after doing that and after hosting the reunion, I definitely look at all other least reunion hosts different. I give them additional grace knowing how much is coming at them and what it takes to try to give balance to the multiple personalities that you're with as well. Definitely. I know we're getting towards the end in I do have to ask you about Rony, but I also need to shout out my co host Troy over on Beyond the Blinds because him and I have been manifesting this for you for years. We've been wanting you on Rononey. We've been needing you on Bravo. I mean I don't know how much you can say Can say anything. Okay. o. But I would just say the fact that I can't say anything would imply there ares things to say. Okay. So I can't say anything right now, but later in the year, I look forward to when I can in fact say More? Okay, okay And y'all know I have like I have no filter, so I'd be happy to tell you everything. But yes, it was not supposed to get out what got out. but I'm gonna lie wouldn't mad that I did' it out. And no I didn't leak it Somebody else did, No, you were tagged in a story. Yeah, I was tagged a story. and I was like, hey, this works for me. but just hope know as the challenge evolves, I hope that the challenge family, right? So all of you guys who have watched the seasons and been with us, I hope you feel, which may sound weird, but like represented Okay. and how I do things in the future or whatever projects I do in the future, I hope you feel like You know when you like Heidi Gardner O S and now used to be an S now went to my high school. Now she graduated the year before I came in, but our high school I went to Sion in Kans City, It's all girl highigh school very like sort of like tighten it. And I know there's a sense of pride whenever I see Hide do Now. H you did know me from a pillow I know that when I see Heidi doing anything, I'm just kind of like, yeah like a science that yeep And I like love that. sameame with people from Kansas City 's from Kans City. So Ted Lasso, yes, we ride. We roll, love it, love to see it. G Ted. also it's a great show. But like I love it And so I hope that there're is that same feeling amongst our challenged community whenever I show up later in the year anywhere else. And with that said, it doesn't mean that if there a moments that there are things you don't agree with, that you can't say, but I hope you know it's the same person you've always known and loved I hope there's just a sense of pride from everyone that like we're represented in other areas in other ways because the challenge in real world are the OGs. Let'sly not forget. All these other things that have come and gone and are amazing and have built their own legacies. But what essional was called a conffessional from real worldor. Yeah. Like that, like that like we that was the blueprint. And so for all the people who remember that era and were part of that era and supported that era, I hope they feel represented And you know we break barriers in terms of crossovers and things. Yeah. you're the first MTV crossover for Bravo. So I'm excited about that. If you are going to be on Rony, I know you, we can't say anything. I mean I was on in season thirteen. Oh Matchmaker. I have been on the show before But if I were to do it again, it would be a big it would not be the same capacity. it would be I'm probably in so much trouble. Don't watch this Bravo. I didn't say anything. I didn't say anything You heard nothing. We'll wrap this up before I get you in even more trouble When I look at your career, I see that you've been a competitor, a host, a matchmaker, a commentator. Now you might be stepping into a different broader world You've reinvented yourself several times already from when we met you on Real Wld Brooklyn. What's something that you hope people get to see from you that they haven't seen yet 's interesting because it's sort of in two ways. And I will say for years, I've still been on TV right as we know, but again, in a hosting role as of late which is much more a reserved role because it's less about me, it's not about me, usually really, right? Like it's about whatever story I'm telling, whomever I'm interviewing, whatever couple, like I'll be on Jenna and Chanele with the Snake showow in July first and then I'll be on again, I don't know, the week after that or two weeks after that they and n. I don't know, but I'm on there all the time. And so but it's not about me. it's about what I'm doing, where being back in a scenario where it is about me. And there was a little bit of that on a show I did called Match Me in Miami on Roku, like three people watched. A actuallyually, it was the number one show on in Roku for like thirty seconds, and then they pulled off far as what they would learn about. So basically twofold. One, it was a little different putting myself because I'm so used to it not being about me and then putting myself in a situation where I needed to lead more of me and when I felt good or you know, right or wrong or whatever and this probably sound like a boring answer, what people might learn about me that they don't already know feel like been so open and transparent from the jump that I don't know that there's that much more to learn about I don't say that there's not that much more, but that this evolution. thinkink of it as an Innctc backstreet boys reunion tour. I don't know if that's a great example. I didn't see them live. so if it was a terrible show, don't judge me. But what I mean by that is just that like when we saw them in concert back in the day, we had an experience, we loved it And we see them in concert now. it's not that they have totally changed. The songs are there, but we're seeing it

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