The Ben and Ashley I Almost Famous Podcast - DeAnna’s Going On A Date

Episode Date: October 5, 2025

It's time! Ben is sending DeAnna on her first blind date at the Jonas Brothers concert. Is she nervous? What's she going to wear? Ben is getting the REAL chat before she heads out on her date.Then later, Ben connects with our spy who is monitoring the date and connecting with DeAnna and the date during the evening.See omnystudio.com/listener for privacy information.

This is an I-Heart podcast. Ah, come on. Why is this taking so long? This thing is ancient. Still using yesterday's tech, upgrade to the ThinkPad X-1 Carbon, ultra-light, ultra-powerful, and built for serious productivity

with Intel core ultra-processors, blazing speed, and AI-powered performance. It keeps up with your business, not the other way around. Whoa, this thing moves. Stop hitting snooze on new tech. Win the tech search at Lenovo.com. unlock AI experiences with the ThinkPad X-1 carbon powered by Intel Core alter processors

so you can work, create, and boost productivity all on one device. Hi there, this is Josh Clark from the Stuff You Should Know podcast. If you've been thinking, man alive, I could go for some good true crime podcast episodes, then have we got good news for you. Stuff You Should Know just released a playlist of 12 of our best true crime episodes of all time. There's a shootout in broad daylight. People using axes in really terrible ways, disappearances, legendary heists, the whole nine yards. So check out the stuff you should know true crime playlist on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

People called them murderers. Ten years later, they were gods. Today, no one knows their names. A group of maverick surgeons who took on the medical establishment who risked everything to invent open heart surgery. Welcome to the Wild West of American Medicine. I'm Chris Pine, and this is Cardiac Cowboys. If you like medical dramas, if you like heart-pounding thrillers, you will love Cardiac Cowboys.

Listen on the IHeart Radio app or wherever you listen to podcasts. Sponsored by Jasper, AI Build for Marketers. Hey, I'm Jay Shetty, and I'm the host of the on-purpose podcast. Recently, I had a conversation with the one and only, Madonna. When I was broke and I had no friends, nowhere to. to live. I was held up at gunpoint. I was robbed. All these horrendous things happened to me. I had such an unhappy childhood that whatever happened to me in New York is better than what my life was. So I'm not going back. Listen to On Purpose with Jay Shetty on the IHeart Radio app,

Apple Podcasts, or wherever you get your podcast. IHeart Podcasts bring you the ultimate summer of love treat. This is famously available. Welcome back to famously available. I'm your host, Ben Higgins, really excited about this episode because we've been getting to know our famously available women and let me tell you they are awesome we got diana and mercedes we've been catching up with them for what seems like months now uh and today i'm sending diana on a date in the real world and she's here with me she's looking beautiful looking flirty am i i thought you were going to keep going. That's why I paused. I was waiting for the multitude of compliments.

Deligant, glamorous, um, looking spunky, all these things. Okay. Spunky. I don't know if I hope this date thinks I'm spunky, Ben. I think spunky's a good thing. Spunky? Okay. All right. So here we go. Um, this is a lot of fun for me.

We've sent you to San Francisco is where you're currently at. You're going to a Jonas Brothers concert. This date will be there with you. I'm very, very excited to ask you. How are you feeling? I am super excited. I have to be honest, the response to the podcast has been really great, but our listeners keep messaging me wanting to know if I'm actually going to date someone.

Like, they're all caught up now and all of the things and they know what I want and what I'm doing, but they would like to know if I'm actually going to be dating. And I was like, yeah, I hope so. I'm just waiting on Ben here. Yeah. Yeah. You know what? We want to get the episodes out there.

So the responses were incredible. We have a lot of options available. I think this is a good option for you, though. Are you nervous at all? No, not right now. I just am like, you know, I'm just trying to find the right outfit to wear, but like my jeans look so great, but they're so tight bin that I'm suffocating,

but it's a good asset, you know what I mean? And I'm really trying to highlight it because I'm going to put one good foot in front of the other. No, I'm not nervous. There's a good word you use there. I'm not nervous. I'm actually really excited, but my hope is that, you know, whomever it is that is coming that I guess is taking it seriously because I realize this is super unconventional to be going on a podcast, to be dating a girl who was on reality

TV a long time ago, you know what I mean? And to be able to think that it could be something. There's a possibility that it could be something. So my hope is that that he's showing. up with great intentions. If he's your friend, I'm going to blame you. I think he is. Do you want to hear a little bit about him?

Yeah, I do. I'm dying. No one will tell me anything. Okay. So first thing, he's tall. Oh, I love it. Love, love, love. We at famously available, find him very handsome.

Oh, we. That's exciting. Easton especially. He grew up in the Bay Area. Okay. He's a dad. Love it. Love it.

Very athletic. Oh, bonus points. He's a nice guy, too. That's the final thing I'm going to share with you tonight. He's a very nice guy. Okay. Is he funny? You have to be the judge of that.

I think humor is something that I can never put down as a characteristic for somebody because I find people hilarious that other people do not find funny. Okay. Is he a Joe Bros fan? I don't know. Or is it going to be like we're a couple of old chumps over here watching the Jonas brothers creeping out? You do have some friends there with you or there's a, I saw some Instagrams last night. I wasn't invited to this party.

That's why I'm doing this virtually. I would have loved to be invited. It's an all girls dinner, Ben. It's an all girls dinner last night. Can you tell us who's there from the show with you? it's it's a lot of fun it's um ashley i is here daisy is here kathy is here susan is here susy is here it's a good group of solid women that's a lot of fun are you getting any of their advice as you get ready for tonight you know what is so funny

is all of the girls were like this is so exciting you're going on a date what are you guys going to do. And I was like, we're all kind of going on my date together. We're all going to be together, which is super exciting. And so the girls were all actually really excited that they're going to get to meet him because I was like, okay, if he's great, we'll have a lot of fun. It's the Jonas Brothers concert. If he's not so great, there's other people in the room to talk to to to help smooth things over. So for me, it's a win-win. It doesn't feel like a lot of pressure. we can just hang out and enjoy good music or we can really hit it off

and it won't matter who else is in the room. Is this more or less ideal than just the two of you going out for the first time alone? To me, this is more ideal. I really appreciate non-traditional dating. You know, I had some friends who were like, oh my gosh, you're going to a concert. Like, you're not going to be able to talk

and get to know each other. But for me, that feels almost like a, relief because what if the conversation does suck? You know what I mean? We just feel so how about Nick? I'm like, Joe, you know? But it's also, it's also pretty exciting because if it is like someone can show up in a scenario like this, you know, and I get it. He's not coming there and it's just going to be me. There's going to be other women in the room. So let's hope he doesn't flirt with all the other women in the room and I can be the apple of his eye this evening. But you know, beggars can't be choosers, I guess, plenty of options to go around. But, you know, I just think that it's a lot of fun.

It's an activity. It's not a typical, like, sit down, get to know each other. There's no pressure to, like, ask hard questions. We can just see if the vibe is there, if we're feeling each other. And if we're not, then we got to go to a concert. We got to eat some good food and we got to enjoy some friends. You know, we've gotten to know you through the last few weeks. I know the responses, as you said, have been really encouraging, but also very curious of if you're ever going to date. Have you taken in any of these comments? Does it add a level of pressure now knowing that there's people listening excited about this? Has anybody given you any insights? Kind of talk about to us the world of getting this show released, having the response, and how it's prepared you

for this moment. Yeah, I'm not putting any pressure on myself. I think it's actually pretty exciting that anybody would want to listen and follow along. And I think that I really appreciate. that there is, you know, a group of women out there who are walking along in the same life phase as I am that are, you know, newly divorced or divorced and are trying to get into the dating world. And pretty much all of them is like, hey, good luck. It's not pretty out there in the wild. And I'm like, yeah, it's a good thing I'm not in the wild. I am like, I am in a controlled zoo here. You know what I mean? Where we get to pet every animal and see which ones we like the most. But for the most part, everyone has had a really good response. And I would say through social media, people have been really

engaging because I just posted the other day what to wear on this date because I haven't been on a date in so long that I don't know how to dress appropriately anymore. Because, you know, I'm in that, like, sweet spot in my life. I'm not like super young, like Susie and Daisy where, you know, I'm trendy. But I'm not like super old like Susan and Kathy. That sounds terrible. I don't mean it. We didn't like that. But do you know what I'm saying? Like I'm not in that bracket yet to where I need to wear like sweaters tied around my neck. So it's a fine line of like, hey, I don't want to look to lucy goosey,

but also comfortable and feeling good in my skin. Do you understand? So that was a lot of fun posting them on social media because I got a really good response from women everywhere telling me what I should wear on this date. And it's kind of fun to bring everybody along. Yeah, yeah. I did two options, Ben.

I was like, myself, jeans, and a cool shirt. Like, that's, I feel best in jeans. Like, that's my comfort zone. And then I was trying to, like, live on the edge and do, like, a skirt and a black top. And I was like, I don't know. This just doesn't feel me. I'll be uncomfortable all night. Like, what if my butt hangs out or, like, I bend over or, like, I have to suck it in all night?

Like, it's the things that us 40-somethings have to worry about Ben. And I'm not just not trying to worry about it. And so luckily, 95% of the women voted jeans in a cute top, and I feel really good about that. Yeah, you should. My advice to you is go with what makes you most comfortable tonight. And it's a concert, right? You can kind of wear whatever you want. I would prefer my vans instead of high heels, but I am, since you're saying he's tall, I'll slip the heels on.

Yeah, you know what? Heels are nice. taking so long. This thing is ancient. Still using yesterday's tech, upgrade to the ThinkPad X1 Carbon, ultra-light, ultra-powerful, and built for serious productivity with Intel Core Ultra Processors, blazing speed, and AI-powered performance. It keeps up with your business, not the other way around.

Whoa, this thing moves. Stop hitting snooze on new tech. Win the tech search at Lenovo.com. Unlock AI experiences with the ThinkPad X1 Carbon, powered by Intel Core Ultra processors. so you can work, create, and boost productivity all on one device. Hi there, this is Josh Clark from the Stuff You Should Know podcast. If you've been thinking, man alive, I could go for some good true crime podcast episodes,

then have we got good news for you. Stuff You Should Know just released a playlist of 12 of our best true crime episodes of all time. There's a shootout in broad daylight. People using axes in really terrible ways, disappearances, legendary heists, the whole nine yards. So check out the stuff you should know. true crime playlist on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. All I know is what I've been told, and that's a half-truth is a whole lie. For almost a decade, the murder of an 18-year-old girl from a small town in Graves County, Kentucky, went unsolved,

until a local homemaker, a journalist, and a handful of girls came forward with a story. I'm telling you, we know Quincy Kilder, we know. A story that law enforcement used to convict six people and that got the citizen investigator on national TV. Through sheer persistence and nerve, this Kentucky housewife helped give justice to Jessica Curran. My name is Maggie Freeling. I'm a Pulitzer Prize-winning journalist, producer, and I wouldn't be here if the truth were that easy to find. I did not know her and I did not kill her Or rape or burn or any of that other stuff that y'all said it

They literally made me say that I took a match And struck and threw it on her They made me say that I poured gas on her From Lava for Good This is Graves County A show about just how far Our legal system will go In order to find someone to blame

America y'all better work the hell up Bad things happens To good people and small towns. Listen to Graves County in the Bone Valley feed on the IHeart Radio app, Apple Podcasts,

or wherever you get your podcasts. And to binge the entire season at free, subscribe to Lava for Good Plus on Apple Podcasts. People called them murderers. Ten years later,

they were gods. Today, No one knows their names. A group of maverick surgeons who took on the medical establishment who risked everything to invent open heart surgery. Welcome to the Wild West of American Medicine. I'm Chris Pine and this is Cardiac Cowboys. If you like medical dramas, if you like heart-pounding thrillers,

you will love Cardiac Cowboys. Listen on the IHeart Radio app or wherever you listen to podcasts. Sponsored by Jasper, AI Built for Marketers. Any questions that you have for him coming off, like, that you're thinking about, you have to get answered or any ice breakers? I used to go with the, would you rather as ice breakers? Shoot, Ben, like, I wasn't feeling any nerves until you start talking. Like, I didn't really have a plan going into this. I just thought when I walk into the room and the door opens and the wind blows and my hair falls back.

He takes one look at me and he falls madly in love and then the rest is all history. But now all of a sudden, I'm like, well, Well, shoot, do I need to open up chat GPT and figure out how our first date's supposed to go? No, no, probably. Probably, okay. You want to hear my icebreaker? Okay. Would you rather be a alligator or a bird?

I'm not going to say that, Ben. Why? I got married from it. No, I need you to send me Jessica's number right now. I'm just, I hate to break it to you, Ben. I appreciate all of your advice in the realm of relationships. and love, but I don't think that I'm going to be going with that one. Wait, are you even going to tell me his name?

No, no. There's zero chance I tell you his name. I have to, like, walk up. He's going to have to guess which one of me is in the room. Do you think he'll know? I think he's going to have a good idea. Do you think I should wear an orange jumpsuit? Yeah, we're going to tell him, we've already told him,

you are the pretty brunette who is going to be so excited to be there tonight. We're excited for you here, famously available. Once this gets started, here's the thing, though. Here's my biggest concern. You want to hear it? Yeah. If this date works, we don't have a season left. Like, we're done. Like, this episode goes one more. We find out, like, that you guys are just perfect and everything's happy and go lucky and we close this chapter. Maybe it's not, though, Ben. Let me pause you. Maybe it's not. Let's say, best case scenario, I go out tonight. I meet this guy at the Jonas Brothers concert. We hit it off. It's all there. He's emotionally stable.

and healthy and also attractive and tall, which we've got. But let's say that we do hit it off. Why isn't there a chance that there's a second date and you follow me through that? A lot can change between now the first date, a second date, let alone the eighth date. Because once people start removing the mask, you know what I mean? Yeah. Then you're talking about real life stuff. Maybe there's beauty in that.

Here's the deal then. We're going to follow you along for as long as you let us. are we manifesting is that what we're doing right now yeah we are we're doing that we're doing the hope the wishes the manifestation and we're going to follow along as long as you let us and then at some point you're going to have to break up with us and you're going to have to tell us oh break up with you i'll have to break up with you i'm not good at breakup spin i think that you can google that and tell yeah you're going to have to tell us you're going to tell us hey please stop following me this is getting weird it's been six years final two questions for you what are you hoping to

get out tonight at its basic level? I think what I'm hoping to get out of tonight, on the most basic level, is just dip my toes and been. It's been a long time since I've been out on a date, a really long time. But there's so much that goes along with that. Like, there's been a long time that I have felt really beautiful. There's been a long time, you know, that I have felt truly desired. It's been a long time that I've actually had to have meaningful conversation with a

person of the opposite sex. So for me, I'm just looking to, you know, get my toes a little wet. That's all. And if it blows me out of the water, then I will welcome that. Could this night end in a kiss? Oh, that would be exciting, wouldn't it? That would be fun. That would be fun. That would be fun, Ben. Sign me up. Are you a Jonas Brothers fan? I do like the Joe Bros. But I like the adult Joe Bros. I felt creepy when they were really young, thinking that the Joe Bros. were cool, but when they released that song where they were dancing around in their underwear and their shirts, what a man got to do? I was like, okay, I'll take Nick or Joe or Joe. Oh, you crack me up. You are in a good, you are on the perfect place. So here is my words for you.

Have a blast. You are incredible. You are beautiful. These are all very true statements that nobody can't deny. Just have a lot of fun tonight because I cannot wait to catch up with you after this date is over right here on Famously Available. We're getting started. Finally. And this is good. I'm so excited. Thanks, Ben. Ah, come on. Why is this taking so long? This thing is ancient. Still using yesterday's tech upgrade to the ThinkPad X1 carbon, ultra-light, ultra-powerful, and built for serious productivity with Intel core ultra-processors, blazing speed, and AI power performance. Keeps up with your business, not the other way around.

Whoa, this thing moves. Stop hitting snooze on new tech. Win the tech search at Lenovo.com. Unlock AI experiences with the ThinkPad X1 Carbon, powered by Intel Core Alter processors, so you can work, create, and boost productivity all on one device. Hi there, this is Josh Clark from the Stuff You Should Know podcast. If you've been thinking, man alive, I could go for some good true crime podcast episodes,

then have we got good news for you. Stuff You Should Know just released a playlist of 12 of our best true crime episodes of all time. There's a shootout in broad daylight. People using axes in really terrible ways, disappearances, legendary heists, the whole nine yards. So check out the Stuff You Should Know True Crime playlist on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. All I know is what I've been told, and that's a half-truth is a whole lot. For almost a decade, the murder of an 18-year-old girl from a small town in Graves County, Kentucky, went unsolved until a local homemaker, a journalist, and a handful of girls came forward with a story. I'm telling you, we know Quincy killed her. We know.

A story that law enforcement used to convict six people and that got the citizen investigator on national TV. Through sheer persistence and nerve, this Kentucky housewife helped give justice to Jessica Curran. My name is Maggie Freeling. I'm a Pulitzer Prize-winning journalist, producer, and I wouldn't be here if the truth were that easy to find. I did not know her and I did not kill her, or rape or burn or any of that other stuff that y'all said. They literally made me say that I took a match and struck and threw it on her. They made me say that I poured gas on her. From Lava for Good, this is Graves County, a show about just how far our legal system will go in order to find someone to blame.

America, y'all better work the hell up. Bad things happens to good people in small towns. Listen to Graves County in the Bone Valley feed on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. And to binge the entire season at free, subscribe to Lava for Good Plus on Apple Podcasts. Hey, I'm Jay Shetty,

and I'm the host of the on-purpose podcast. Recently, I had a conversation with the one and only, Madonna. When I was broke, and I had no friends, nowhere to live, I was held up at gunpoint, I was robbed,

all these horrendous things happened to me. I had such an unhaping. happy childhood that whatever happened to me in New York is better than what my life was. So I'm not going back. Listen to On Purpose with Jay Shetty on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. I recently sent single Diana Poppice out to a Jonas Brothers concert for her first set up date here on the show. Now, we always invite the dates to come on the show and give their perspective as well. But this date has opted to not come on the podcast. But I've got someone else who was there and witnessed everything go down that night.

So before I connect with Deanna this week and we get her thoughts, opinions, feelings, emotions, all those things about the date. I thought I'd connect with Cynthia, who was kind of observing the date and hanging out with them all night long. Cynthia, welcome to famously available. Thank you for having me. I feel like I'm this undercover spy doing like romance romance recon. You are. You're 100% that for us today. We are here because we're curious. We're going to have Deanna on and she's going to share her thoughts and perspective on everything, kind of what she was going through. But I think that's going to come from more of a personal place for her. And I do think it's always helpful to have an outside perspective come in. and share what they were seeing. You were there for the evening at this concert. You met Deanna that night, correct?

I did. That was the first time meeting her. Okay. And so then did you meet her date that night as well? I did. So I met both of them for the first time that evening. Let's talk about Deanna because that's who we love and care about here. How was she feeling, looking?

What was kind of the vibe that you were picking up on walking into that night? She had such great energy. first of all she was dressed amazingly she looked super hot she was really outgoing and open and talking to a lot of people like she is such good energy like you can't not help but fall in love with her like honestly she did everything right when it comes to i think dating which is being presentable but not being like too presentable if that makes kind of sense like she was just there to have a really good time and i think that's the energy you want when you're dating. What about his vibe then? Same thing. Like, really good looking, super approachable, like, great to talk to.

And then when I saw the two of them talking, like, I really thought there was a vibe there. Okay. So you're hinting at something from your perspective. Was there a vibe between them? I thought there was. I really thought, like, there was good body language when, you know, your kind of facing towards the person and you're open to speaking to them, close enough that you can have a conversation. It definitely seemed vibey. Now, we were worried about this here

famously available. This was obviously an incredible event and a really fun event to be at, the Jonas Brothers concert. We had sweets. We had everything set up. But concerts are, I don't think, like, ideal for first dates. They're loud. There's other people around. You want to to have a good time, you want to enjoy the music, so you don't want to be talking the whole time. Do you think that possibly some of the night was either enhanced by the concert, or did it feel like the concert was a difficult place to have a first date? Oh, that's such a good question. I like the concert idea as a, it's like a great meet cute. Oh, we met at a concert. We kind of hit it off. Like, let's go to coffee the next day or a couple days later.

the thing with that particular suite, if you've been to private suites before, there's two different versions. One where there's like a glass wall and a door so you can have like an indoor outdoor situation where there's like stadium seating outside, but you can still have an indoor experience and it's a little bit quieter. This was unfortunately not that case. It was wide open. So even if you were like inside where there's like sofa and and the food, it's still a full-blown concert experience where it is really loud. So I, I could see where it could be difficult. You are having a conversation.

You're kind of meeting. Everyone's having a good time. But it is so incredibly loud that I don't think you necessarily get the best version of like necessarily a first date. I would say meet cute. Okay. I'm really shocked that them seeming like they were having a really good time together, that there wasn't a, let's get together and get to know each other more. That's kind of where we're sitting right now. We did hear that he, and maybe you weren't around for this or maybe you are familiar with this,

we have heard that he asked her to go outside and talk at some point. And she did not agree to that. I don't know if you're around for this part. What happened? Are you familiar with it? That I didn't see. I did not see them leaving to talk outside. I probably would have noticed that.

I left about 15 minutes before the end of the concert. I'm old. I wanted to miss the traffic. I'm with you. I would have done the same. So I didn't see that. But I'm glad that he did. But again, I'm still shocked that there wasn't a get-together. I do feel like we're all at a certain age that even if it's not like or give it a chance, I guess is what I'm saying. You know, even if you might not have that romantic spark right away, meet new people.

just get together for that second chance, like go out and have a coffee with someone and just see. Worst case scenario, I don't think it's the worst thing to say, like, I'm going to put you in the friend zone because we could all use more friends when you get into your 40s and your 50s. It's not like a horrible thing, and you never know that person might have friends. It might be a better fit for you. So just the fact that he wasn't into even getting together after, I really am shocked because she, again, had such good energy. like how could you not want to get together unless i mean he's divorced she's divorced i don't know how newly divorced he is like was it so new for him that maybe the timing was off because

timing is so important too it is important so you know what we've picked up on i don't did you ask either of them kind of what their feelings were towards each other at least initially no because i didn't want to interrupt like it was like kind of like things were like looking really good. Ah, come on. Why is this taking so long? This thing is ancient. Still using yesterday's tech,

upgrade to the ThinkPad X1 Carbon, ultra-light, ultra-powerful, and built for serious productivity with Intel core ultra-processors, blazing speed, and AI-powered performance. It keeps up with your business, not the other way around. Whoa, this thing moves.

Stop hitting snooze on new tech. Win the tech search at Lenovo. unlock AI experiences with the ThinkPad X1 Carbon powered by Intel Core alter processors so you can work, create, and boost productivity all on one device. Hi there, this is Josh Clark from the Stuff You Should Know podcast. If you've been thinking, man alive, I could go for some good true crime podcast episodes, then have we got good news for you. Stuff You Should Know just released a playlist of 12 of our best true crime episodes of all time. There's a shootout. and broad daylight, people using axes in really terrible ways, disappearances, legendary heists, the whole nine yards. So check out the stuff you should know true crime playlist.

On the iHeart Radio app, Apple Podcasts, or wherever you get your podcasts. All I know is what I've been told, and that's a half-truth is a whole lie. For almost a decade, the murder of an 18-year-old girl from a small town in Graves County. Kentucky went unsolved, until a local homemaker, a journalist, and a handful of girls came forward with a story. I'm telling you, we know Quincy Kilder, we know. A story that law enforcement used to convict six people, and that got the citizen investigator on national TV.

Through sheer persistence and nerve, this Kentucky housewife helped give justice to Jessica Curran. My name is Maggie Freeling. I'm a Pulitzer Prize-winning journalist, producer, and I wouldn't be here if the truth were that easy to find. I did not know her and I did not kill her, or rape or burn or any of that other stuff that y'all said. They literally made me say that I took a match and struck and threw it on her. They made me say that I poured gas on her. From Lava for Good, this is Graves County, a show about just how far our legal system will go

in order to find someone to blame. America, y'all better work the hell up. Bad things happens to good people in small towns. Listen to Graves County in the Bone Valley feed on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. And to binge the entire season ad-free, subscribe to Lava for Good Plus on Apple Podcasts.

Hey, I'm Jay Shetty, and I'm the host of the On Purpose podcast. Recently, I had a conversation with the one and only, Madonna. When I was broke and I had no friends, nowhere to live, I was held up at gunpoint, I was robbed. Always horrendous things happened to me. I had such an unhappy childhood that whatever happened to me in New York is better than what my life was, so I'm not going back. Listen to On Purpose with Jay Shetty on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. A little bit of personal information about you kind of heading up for our last group of

questions here. What is your romantic situation? I'm married. So I was talking to him, but I also feel like I'm married. I'm wearing a ring. People ask me about my husband. We had mutual friends in common who know my husband because we go to high. We went to high school together, and people that we went to high school with were there. So I kind of feel like I'm that safe person to talk to. I'm kind of like the gay best friend. Like, easy to talk to because I'm not, nothing's happening here. So I don't know if like he felt comfortable talking to me because I am married.

Yeah. But if you two did speak, he didn't at all hint either way of what he was thinking towards Deionette, to you. Not at all. No. Which I also think, again, is really respectable too. Like, you know, it's not like we're in. our 20s and it's like, oh, she's a haughty.

Like, I don't think people do that. I think just the fact that they were really connecting and they had a good energy. And again, like, body language is so important that the body language was there. Again, like, to say that they're not having a coffee, like, just shocks me. Yeah. If I was gay and I was single, I date her. She's so nice and awesome. She is.

Like, she's like the package. She's a great package. She's great. She's awesome. That's what we have her here, famously available. She needs to come to New York City. I feel like this could be a good place for her. Yeah, it's a little more maybe down, have more people kind of within what she's looking

for. But I was given advice when I was single by somebody, and I think it's great advice. When you're single, especially as you get older and our single, just keep dating. Go on weird dates. Go on good dates. Go on funky dates. Just keep dating because at some point. you're going to kind of figure out what it is that maybe brings out the best in you.

And so for the two of them, as they're both divorced and they're looking to get back out there in the dating world, I do, I am surprised that there isn't a follow-up date. And we're going to get maybe more information on that here when we bring Deanna on this week and figure out, you know, from her perspective, why there isn't a second follow-up date. But if she listens to this, which she will, and you were to give her advice specifically. take away that this date worked or didn't work, but just as she continues on this journey, what advice do you have for somebody in their 40s and 50s that are looking to date and trying to date and trying to get back out there? I think you nailed it. Number one is keep dating.

I look back after breakups and the people I dated right after breakups. I almost want to apologize to them because they didn't get my best self because I was so new to it again. You have to keep dating to get comfortable with it. And it's also about you being comfortable with dating and showing your true self and not your dating self. Like you want to show your real personality. And I think number two, do the things that you love to do because then you're going to be, A, happy because it's what you love to do and you're going to be around people who also have the same commonalities. Like, if you love to run, join a running club. If you love to cook, take some cooking classes. Do things that are your passion, and then you're going to attract the people that have the same passions as you.

And I think that's really important. But no matter what, just keep getting your dating legs under you. You have to just keep going out and putting yourself out there. Yeah, it's daunting. I know it is. It's a big, it's daunting. But I think once you get, like you said, your dating legs, the pressure gets taken off. Every date seems important, but less important.

So you're not putting all your weight into it. it becomes kind of a skill set, a habit. And hopefully at the end, you can find somebody. Final question for you, Cynthia, we've kind of gone through the whole evening from your perspective, the good, the bads, what you thought. When the two of them walked in and you met them both the first time, was your first interaction one of, oh my gosh, I could actually see these two as like they're a couple, or was it like these two have totally different vibes?

no actually i could totally see them dating yeah i really could i think they have a lot of things in common from what i talked to both of them about um it really just could be timing and with the place so i don't think when it comes to dating i would just tell her number one don't take things personally either it had nothing to do with her she did everything right she was herself she was personable she was outgoing she was lovely to speak to She looked incredible. She was the package. So it's not about you.

It's the other person. And that's okay. Because that does not mean that your person's not out there. It just has to mean that you haven't met them yet. That's right. Well, Cynthia, make us a deal here. If we bring Deanna to New York City to put her on a date, you are going to go sit like a table beside them and spy on them as well.

Yes, I'm going to put on a trench coat. I've got my sunglasses. And break it down for it. right here at famously available. Cynthia, thank you for coming on. Thank you for going on the date. I hope you had a great time. But also, your insight is very helpful.

We appreciate you. Anytime. I've got her back. I'll be her wing woman here in New York. I love it. Thanks, Cynthia. Thanks, Ben. All right, so we've gotten Cynthia's perspective on the day.

That's an outsider looking in and giving us everything she saw. But stay tuned to this week as we get Deanna on the show to hear her perspective. on why the date worked or didn't work, or maybe there's some insights that we just aren't knowledgeable of right now

that will help bring clarity to the situation at hand. So stay tuned. Until next time, I've been Ben. Ah, come on. Why is this taking so long? This thing is ancient. Still using yesterday's tech, upgrade to the ThinkPad X1 Carbon,

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