The Ben and Ashley I Almost Famous Podcast - I Do Part 2 In The Wild

Episode Date: May 31, 2025

Jana Kramer has sent her friend Pamelyn out into the world to find love and her wingwoman is Kelly Bensimon.They are back from the BottleRock/Justin Timberlake show, and it’s time to hear every messy detail.  Did they approach any guys? We’re there any love connections?  Any kisses or did they crash and burn?The women are spilling all the details from their night out in Napa! Did they complete their challenges for the night? Listen to find out! Email us at: [e-mail] or call us at 844-4-I Do Pod (844-443-6763)Follow I Do, Part 2 on Instagram and TikTokSee omnystudio.com/listener for privacy information.

This is an I-Heart podcast. My boyfriend's professor is way too friendly, and now I'm seriously suspicious. Wait a minute, Sam. Maybe her boyfriend's just looking for extra credit. Well, Dakota, luckily, it's back to school week on the OK Storytime podcast, so we'll find out soon. This person writes, my boyfriend's been hanging out with his young professor a lot. He doesn't think it's a problem, but I don't trust her. Now he's insisting we get to know each other, but I just want her gone.

Hold up. Isn't that against school policy? That seems inappropriate. Maybe find out how it ends by listening to the OK Storytime podcast and the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hello, it's Daniel Fischel. Writer Strong. And Will Ferdell from PodMeets World. We are back in Las Vegas and giving the people what they want, a full week of Y2K content. Tell me why. Well, for the Backstreet Boys residency at Sphere, of course.

We joke and say this is our second marriage, but it takes a lot of communication. Plus, it's carrot top, baby. And finally, Ashley Simpson-Ross joins us to talk about her upcoming sold-out Vegas residency. Listen to PodMeets World on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. December 29th, 1975, LaGuardia Airport. The holiday rush, parents hauling luggage, kids gripping their new Christmas toys. Then everything changed. There's been a bombing at the TWA.

terminal, just a chaotic, chaotic scene. In its wake, a new kind of enemy emerged, terrorism. Listen to the new season of Law and Order Criminal Justice System on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, I'm Jay Shetty, and I'm the host of the on-purpose podcast, and today I'm joined by one of the greatest athletes of all time, Novak Djokovic. He's won 14 grand slams in a glittering career. Novak, Djokovic.

When you reach your 30, you start counting your days to your retirement. I'm 38 this year. How long can I push my own limits? Listen to On Purpose with Jay Shetty on the IHart Radio app, Apple Podcasts, or wherever you get your podcast. Hi, my name is Enya Yumanzoor. And I'm Drew Phillips. And we run a podcast called Emergency Intercom. If you're a crime junkie,

and you love crimes, we're not the podcast for you. But if you have unmedicated ADHD... Oh my God, perfect. And want to hear people with mental illness, psychobabble. Yes, yes. Then Emergency Intercom is the podcast for you. Open your free IHeartRadio app. Search Emergency Intercom and listen now.

It's I Do Part 2. I'm Kelly Ben-Simon, one of your celebrity mentors here on the podcast. We're here at IHeart, Ferbo, podcast house with my new friend Pamela. And we're absolutely loving this Italian-inspired villa. Pamela, what's your favorite part of the villa? The view. The view is fabulous. The view, the pool, the tennis, the exercise room. all the bedrooms, all the space.

Incredible. Incredible. We had so much fun. It's like stepping into a dream. This is just one of the amazing properties you can find on Verbo. Check out their 2025 vacation rentals of the year and book your next getaway on the Verbo app. Plus you can earn rewards with their one key program.

It's an amazing deal. All right. So last time the listeners heard from us and we talked all about the kind of things. each of us are looking for it, a partner. And what we don't want and what we do want, then we headed out to Bottle Rock Show, and we kind of had some goals in mind. So let's recap. All right. Did we find anyone that was attractive? No. Did we have fun? Yes. Yay!

But let's like bring it back. I mean, I don't mean to say no so bluntly. I think it was just a unique environment, right? Like, we're there to, like, enjoy this concert and, you know, Benson Boone and Justin Timberlake. And so when your focus is on something else and you don't truly have the experience of being at Bottle Rock, so it was a little bit kind of, you know, like trying to, you know, like do one thing, but still experience another thing. I mean, it was so great. Like the music was unbelievable. The food was phenomenal. I think we tried absolutely everything there.

And then the wine. People were like sitting there with their crafts of like the most beautiful wine. And just the vibe was so it was just great. It was sophisticated. Everyone looked great. It was just so elegant. I mean, I wasn't looking at men because I was looking at all of these women just in the most amazing outfits and so creative. and yeah, stylish.

So I really love that. I know. It was really fun. I tried to situate us right near like the food court area where like there was people had to go to the bar and get the food. So I was like there was a lot of traffic for people. You get A for effort. She tried, you guys.

It was really fun. We had a lot of fun. We had a lot of fun. So do you think there was any flirting or? No. No. okay um did you did you have to use do we have to use any code words no no we did not have to use yes we did not have to use any code words um it was funny because there was one guy that I was like

oh he's really good looking you're like no so I was like okay that's fine so I remember the one that was the one that was the Spanish guy he was very good looking I don't remember that one the guy when you were getting the sushi and he was like oh don't leave no and I was like that's my Spanish accent and he was like he was like Don't leave. I was like, don't, oh, okay. And we were like, you are looking at each other and we're like, we're not leaving. We're in the line to get sushi.

Yeah, he was, yeah. I mean, I think like there were, you know, a bunch of just like attractive people in general. I think that that was, you know, what I, there was a lot of couples. There were a lot of couples. A lot of couples. Okay, there was that the two guys that may have not have been marketing their t-shirt line, which I was not aware of. I thought I was really going in because I was.

I was like, remember in the one of the things? It was like, okay, we did you get them to buy our drinks? And so I was like, these are the guys who are going to buy the drinks. Even though I wasn't drinking alcohol. I wasn't drinking either. We knew the rest of drinking alcohol. But your drink, your lemonade kind of looked like it was like some kind of like Cosmo vibe.

I was drinking a liquid death. But I was like, oh my God, they're going to definitely ask us. Crickets. No. It was crickets. They were like just trying to promote their t-shirts. And I didn't understand. I was like, because I really wasn't paying attention to the T-shirts, not to

I would say they were like the last people that would be buying us a drink. They came to Bonarok to wear the T-shirts that they're making to promote themselves. Like they, that's their promotion. That's their marketing budget. I actually thought they don't have money to buy us a drink. I actually thought the one woman that was wearing the rose gold ray bands and then her friend that had those really cool pants on, they would have been like, what kind of wine do you want? Let's hang out.

Let's, you know, just chill out. listen to music. We had a better chance of women buying us a drink than those two men, for sure. Did we get a phone number? No. We failed. We failed miserably. We did not fail. We had Fs for everything. We were just like, we weren't good enough. We just didn't fail. Fail is like definitive. You know, just wasn't good enough means there's possibility for growth. Well, you know, I, this like reminds me. so much of just going out with my friends in my 20s and we would go out dancing. And we would come home and have the most amazing stories about that night. But it was all about us enjoying each

other. Like we wouldn't remember one other person that was actually at the club. It was about us having fun. And so that's like the same thing that always happens to me is I don't like purposely look. You know what I mean? And so we were trying a little bit to like do it. Because it was fun and that's what we said, you know, we were going to do, which was sweet. But I think in real life, at places like that, it just doesn't work like that. Like when you're forcing something or when you're like looking too hard. What I think was good is that like, because we kind of had this like fun plan, that it like set us up for success with our own vibe and for just to like have fun and people were coming towards us and talking to us because we were having so much

fun. Sure. I mean, the two guys with the weird t-shirts, I remember when I said I wanted to have you dance, I did pull out some of my dance moves. I don't know if you saw that. I tried to like, I tried to like wave at you to see if you were, but you, I think you were turned around. Anyway. Probably. And you're back to me. And we danced. I mean, I did dance the whole night. We did. We danced. I just didn't. I just didn't dance with a man, but I danced the whole night. Yeah, I took you into the pit or like walking through. Don't you think I'm really good at navigating? You're really good.

I think you're just like this just tall, just wonder, like walking through this crowd and they just like split open for you to walk through it. I'm just a short little, I just follow. I'm like right behind and it was the most clear path ever. I'm like, let's go this way. Let's go that way. I mean, it was very, it was warm in there too. It was like, it was very, it was really.

Yeah, we needed body heat. We needed a big sweatshirts. But you know what? We had so much fun. on. I literally loved it. So, you know, we talked before that we're not really attracted to the same kind of guys. And, like, you were like, I like suits. And I'm like, this is not a place for any those suits. I think one guy had tennis shorts on. There were bougie tennis shorts. But I did not see one suit. So I was like, oh, that was definitely not the. And are suits like, you know,

where do people even wear them anymore, right? I mean, I love a guy in a suit too. Yeah. I mean, I guess in this in New York City. I may or may not have enlisted Tamara with some advice as to what I should do to create more buzz around getting guys. She was like, what are you talking about? About getting guys for you? Just in general. Like, I'm just trying to get guys. I mean, that was, I had a mission.

I was on a mission and I wanted to, like, bring people and just see what was going on. She was making me laugh so hard. She was like, telling, no, that's not how it works. She's like, I'm like, no, no, I was dancing. She's like, no, don't dance. What does she want you to do? She didn't, she didn't say, she didn't give me advice. She was just like, don't dance.

I was like, should I dance? She's like, no, no, no, no, don't dance. No, no, that's not cool, Kelly. That's not cool. You know, she's in this gorgeous, had this gorgeous dress. And like, her beautiful husband, the two of them were like this picturesque couple. And I'm like, what do you think we should do? She was like, not what you're doing.

I was laughing. Well, that's what I mean. It's, you know, fun. When you try too hard sometimes. like to get and just be yourself and yeah and I think naturally organic and we were in the car with the girls for bachelor nation like we're just because I was really like I just loved this morning when you were talking about like how happy you are in your life and like I really and I say this all the time but the kinetic energy and just like when you say things like how happy you are

just makes people feel good so like when you're like so what tonight what made you feel happy Music makes me feel so happy, especially, you know, music that takes you back to, like, certain times. So Justin Timberlake does that for, I think, so many people, especially, you know, in our, like, era. Yeah. So it's nostalgic. And I think that's, like, I blast music all day long. It's my therapy. It's, like, anywhere from, you know, Whitney Houston to Teddy Swims, like, all day long. I don't know, takes your mind to a different place. I love that. I love that.

December 29th, 1975, LaGuardia Airport. The holiday rush, parents hauling luggage, kids gripping their new Christmas toys. Then, at 6.33 p.m. Everything changed. There's been a bombing at the TWA terminal. Apparently, the explosion actually impelled metal, glass. The injured were being loaded into ambulances. Just a chaotic, chaotic scene.

In its wake, a new kind of enemy emerged, and it was here to stay. Terrorism. Law and order, criminal justice system is back. In season two, we're turning our focus to a third. threat that hides in plain sight. That's harder to predict and even harder to stop. Listen to the new season of Law and Order Criminal Justice System on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. My boyfriend's professor is way too friendly, and now I'm seriously suspicious.

Oh, wait a minute, Sam. Maybe her boyfriend's just looking for extra credit. Well, Dakota, it's back to school week on the OK Storytime podcast, so we'll find out soon. This person writes, my boyfriend has been hanging out with his young professor a lot. He doesn't think it's a problem, but I don't trust her. Now, he's insisting we get to know each other, but I just want her gone. Now, hold up. Isn't that against school policy? That sounds totally inappropriate.

Well, according to this person, this is her boyfriend's former professor, and they're the same age. And it's even more likely that they're cheating. He insists there's nothing between them. I mean, do you believe him? Well, he's certainly trying to get this person to believe him because he now wants them both to meet. So, do we find out if this person's boyfriend, really cheated with his professor or not? To hear the explosive finale, listen to the OK Storytime podcast

on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Hello, it's Daniel Fischel. Writer Strong. And Will Ferdell from PodMeets World. And we're bringing you Viva Las Content. That's right. We are back in Las Vegas, the city of sin, and giving the people what they want. A full week of Y2K content.

Wait, we're back in Vegas? Tell me why? Well, for the Backstreet Boys residency at Sphere, of course. We sat down with Kevin Richardson and A.J. McLean just minutes before they took the stage, and our very own Wilfredel basically became the newest member of the band. Boy band, please. Plus, the man who has the longest running comedy show on the strip joins us and gets his props. It's carrot top, baby.

And finally, we all L-O-V-E-Hur. Ashley Simpson-Ross joins us to talk about her upcoming sold-out Vegas residency. It's a full week of nostalgic interviews you don't want to miss. Listen to PodMeets World on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, I'm Jay Shetty, and I'm the host of the on-purpose podcast, and today I'm joined by one of the greatest athletes of all time, Novak Djokovic. The world's number one male tennis player. He's won 14 grand slams in a glittering career. Novak Djokovic! You've been through so many injuries, losses. I always told himself what has Novak Djokovic done?

What goes through your mind when you lose? I just want to be left alone. What has it taken to become Novak Djokovic? It's a consistent practice. It's prayer work, mindfulness, meditation, conscious breathing. It requires more responsibility from you on a daily basis to prepare yourself for the biggest battle. When you reach your 30, you start counting your days to your retirement.

I'm 38 this year. How far can I go? How long can I push my own limits? Listen to On Purpose with Jay Shetty on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Have you ever wished for a change but weren't sure how to make it?

Maybe you felt stuck in a job, a place, or even a relationship. I'm Emily Tish Sussman, and on she pivots, I dive into the inspiring pivots of women who have taken big leaps in their lives and careers. I'm Gretchen Whitmer, Jody Sweetie.

Monica Patton. Elaine Welteroff. I'm Jessica Voss. And that's when I was like, I got to go. I don't know how, but that kicked off the pivot of how to make the transition. Learn how to get comfortable pivoting because your life is going to be full of them. Every episode gets real about the why behind these changes and gives you the inspiration and maybe the push to make your next pivot. Listen to these women and more on She Pivots, now on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts.

So which one was your favorite? Did you like Justin or did you like Benson better? Justin Timberlake or Benson Boone? I saw Benson Boone already, like his full concert. I took the girls. So that was so fun. We went to Nashville. And I never saw Justin Timberlake perform until tonight.

So I was, yeah, I was excited to see him probably more. I mean, he's just like iconic, you know. I saw it at Barclays. And it was, first of all, Barclays is just. just a beautiful, beautiful arena. But he was phenomenal. I mean, he's just an amazing dancer, singer. Like, I love, you know, the Tennessee kids.

I love the whole thing. I just like the vibe is really great. Yeah, his presence. And I really, one thing I really, really like about him, or even tonight was when the woman gave, showed him the jacket that she had embroidered. And he was like, I'm going to sign this. And he was just really, he's very, like, engaging with his fans, which I think is so cool. I mean, 25, 30 years he's been doing this?

I mean, you could tell he just really still wanted to be there. He loves it. He loves it. Just to have a tour, right? Yeah, 25 years later to have such a big tour. Yeah. I mean, Benson Moon is over the top. He's a smoke show.

You're going to hear it right now, I'm going to tell you he's going to be the next Calvin Klein. He is, his vibe is very Calvin Klein. That's what he's going to do. I'm forecasting that. Did you hear that, Ben, I'm here for it. He is just a doll baby. Like, I just adore him. And his new song about the mother? I was like, oh my God. I was like, okay, late on the timing, but great song. Yeah. I'm like, Mother's Day passed. So we were like, that would have been a really good song

for me, but, um, to listen to. But I mean, I was just like, oh my gosh, I think I'm, I'm like tearing up. Yeah. No, he, he's, I mean, his flips. I could just watch him do those flips all day long. Yeah. Like, who can do that? You just, he just stands. And then. flips. But Benson, do not think that Pamela thinks you're her type because you're not. She likes guys and suits. I could be his mother. Easily. I could be your mother. Oh, my God. So just to kind of wrap things out, what are your feelings in love? And like, what do you want to tell the listeners about going through it? Wow, that is just a very layered question, Kelly. What are my thoughts on love and divorce?

Or what are my thoughts on? Just like after today, like we've been talking about relationships with a lot of different people of all different ages. And we saw a lot of people tonight that were like really in love all these different couples. And I just wanted to like, you know, what's your like takeaway from today and like how do you feel about love? I think what really hit me was I was talking to all of those young bachelor and bachelorette girls and they were the sweetest and they came up to me and they were just like, we love you. We want to be like you when we're older and you, you know, like how you take care of yourself and how happy you are and your personality and how you were explaining things to us about like

health and wellness and what we should do, you know, to, to, like, not have to worry so much, you know, when, when they get to my age. And it just made me, no matter, like, what has happened, like, in, you know, the past with, like, getting divorced and all of this, if you don't love who you are, like, you're never going to be successful, you know, finding another love or having, you know, exactly kind of, like, what you want. And so at the end of the day, like, that's just what I focus on. I love that. Treating myself, loving myself, like, really, truly, like, I, and I know people say that,

and it's always overused in this whole self-love and is, are people really doing it? You know, and, like, what does that mean to people? And it can mean a number of different things, but just hearing, like, almost like, somebody, other people saying that that's kind of like what I project and that I'm showing that that to my girls and, and I'm showing that to my clients and like all these people that I care about. That's what I have control over. I don't have control over the next stages and will there be, you know, this new amazing love. Like I have hope and I truly believe that it will. But I think the first step is, you know, loving yourself and really just, like, focusing on that

and not stopping what you want to do in life just because you don't have a partner. Right. I mean, that's, I think, like, the biggest takeaway, too. It's like love being by yourself, travel by yourself, do all of these things by yourself, because once you realize how amazing you are, I always want to be by myself. Like, I choose me. Right. I love that.

But it's also like, you know, it's like you don't always get what you want, but you get what you need. And that's so true because, you know, if you are taking care of yourself and you do have respect for yourself. Right. Those people are going to, there's that's that person that you really want to be attracted to or, you know, be attracted to you, is that he's going to be there because he's going to be your mirror image. Yeah. And I totally believe that. that 100%. And no, it just was like refreshing to hear, you know, another contemporary talk about just being genuinely happy. I mean, there's, there's, I, I'm around so many people who are just

like blaming and shaming other people all day long. And it's just so nice to be around someone who is just like, I'm excited about my future. I love my kids. And, um, I'm just excited to hear about your journey, your love journey. I know it's going to be great. Oh my gosh. Well, same. And I just learned so much from you too. I mean, just about health and wellness. And I heard with you on the phone with your daughters. And they're so cute and so excited. And they have such amazing energy. And it's just such a special time with them. And, you know, there's just so much to look forward to. There is. There really is. And it's just interesting because it was like serendipitous to be at a place like bottle rock and to see all these people that were just like

really enjoying themselves, like naturally and inherently enjoying themselves, it just made it, it was just like, it was like a very warm, it was like a hug there. I was like, oh my God, this is amazing. I love Napa. Well, just like the energy with, you know, a man or a girlfriend, it's, that was that energy that I felt when I walked in there. It was like that homey, comfy, cozy feeling that, like, any of that would resonate with me, whether it's a friend or a, you know, a lover or whatever it is. And that's kind of like, you just felt really homey in there. Yeah.

I just regret not getting the Lula Lemon sweatshirt, but that's a side note. They weren't sold out? Everything was sold out. I was like, I think I'm going to get a sweatshirt. No. I was like, I'll take the double XX out. They're like, no. It was just so cold.

We don't have anything. Nobody was prepared. I know. We were walking in. I'm like, um, these girls, the, the Bachelor girls, they didn't have coats and they had on spaghetti-strapped dresses. I'm like, they're going to be really cold.

So they all had to buy the sweatshirts. Yeah, it was so fun. It was so fun. Well, thank you so much. We need to hear more from Pamela. We need to know what's going on. I'm not going to tell you guys again, like some of your tricks of the trade,

but you have to listen to the podcast with Jana and hear some of the banter back and forth because it's amazing. I was listening to it last night. I was like, oh, my God, these guys are unbelievable. I love that. I love Jen. We should all do something together, like the ring of us.

I would love that. Yes. I would love to hear, like, you know, what's happening in Tennessee. So, yay. Yay. Thank you so, so much for joining us at Bala Rock and in Napa. We had so much fun. Thank you for having me.

You're so sweet. Yay. Having a wing woman has been so much fun. Are you ready to date again? not having the best luck. Tired of being single, we can help. Email us or call us all the infos in the show sheets. Follow us on socials and make sure to rate and review the podcast. I do part two, an IHeartRadio podcast where falling in love is the main objective. I'm seriously suspicious.

Wait a minute, Sam. Maybe her boyfriend's just looking for extra credit. Well, Dakota, luckily, it's back to school week on the OK Storytime podcast, so we'll find out soon. This person writes, my boyfriend's been hanging out with his young professor a lot. He doesn't think it's a problem, but I don't trust her. Now he's insisting we get to know each other, but I just want her gone. Hold up. Isn't that against school policy?

That seems inappropriate. Maybe find out how it ends by listening to the OK Storytime podcast on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Yes. Hello, it's Danielle Fischel. Writer Strong. And Willfordell from Pod Meets World. We are back in Las Vegas and giving the people what they want. A full week of Y2K content.

Tell me why. Well, for the Backstreet Boys residency at Sphere, of course. We joke and say this is our second marriage. But it takes a lot of communication. Plus, it's carrot top, baby. And finally, Ashley Simpson Ross joins us to talk

about her upcoming sold-out Vegas residency. Listen to PodMeets World on the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. December 29th, 1975, LaGuardia Airport. The holiday rush. Parents hauling luggage, kids gripping their new Christmas toys. Then, everything changed. There's been a bombing at the TWA terminal. Just a chaotic, chaotic scene. In its wake, a new kind of enemy emerged. Terrorism.

Listen to the new season of Law and Order Criminal Justice System on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Hey, I'm Jay Shetty, and I'm the host of the on-purpose podcast, and today I'm joined by one of the greatest athletes of all time, Novak Djokovic. He's won 14 grand slams in a glittering career. Novak Djokovic! When you reach your 30, you start counting your days to your retirement. 38 this year. How long can I push my own limits?

Listen to On Purpose with Jay Shetty on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. Hi, my name is Enya Yumanzoor. And I'm Drew Phillips. And we run a podcast called Emergency Intercom. If you're a crime junkie and you love crimes, we're not the podcast for you. But if you have unmedicated ADHD... Oh my God, perfect. And when a... to hear people with mental illness, psychobabble. Yes, yes. Then Emergency Intercom is the podcast for you. Open your free IHeart Radio app.

Search Emergency Intercom and listen now. This is an IHeart podcast.