Second Date Update: Pawn Shop Shopping Trip
19 min
•Mar 2, 2026about 2 months agoSummary
Gage took Ainsley on a last-minute, unplanned first date to a strip mall where they went antiquing and visited a pawn shop. During the date, Ainsley discovered Gage was attempting to sell his ex-girlfriend's engagement ring to pay for dinner, which he never disclosed to her. The hosts helped facilitate a second date after Gage called the show seeking a redo.
Insights
- Communication and transparency are critical in dating—Ainsley was more bothered by the secrecy than the actual activity of selling the ring
- Last-minute, unplanned dates can work if the person is genuinely interested, but planning and intentionality signal respect and commitment
- Financial constraints during dating (wanting to avoid credit card debt) can be reframed positively if communicated honestly upfront
- Shared experiences and activities (like antiquing/pawn shopping) can create bonding opportunities even in unconventional date settings
- Men often underestimate what women notice—lack of planning, secretive behavior, and poor communication are immediate red flags
Trends
Non-traditional first date venues (antique shops, pawn shops) gaining acceptance as alternatives to dinner/drinksFinancial transparency and cash-based dating becoming more relevant in discussions about modern dating expectationsRadio/podcast-facilitated relationship interventions as a form of entertainment and relationship coachingDating show format evolution: moving from matchmaking to relationship repair and second-chance facilitationYounger daters valuing authenticity and communication over polished, expensive date experiences
Topics
First Date Planning and ExecutionCommunication in Dating RelationshipsFinancial Transparency in DatingUnconventional Date VenuesMale-Female Dating ExpectationsRelationship Red Flags and Warning SignsSecond Chance DatingPawn Shop CultureAntique Shopping as Dating ActivityDating Show Format and Entertainment
Companies
iHeartRadio
Podcast distribution platform where the show and related content are available to listeners
People
Gage
Listener who called the show seeking help with a second date after an awkward first date at a pawn shop
Ainsley
Woman who went on first date with Gage; discovered he was selling an ex-girlfriend's engagement ring during the date
Brooke
Co-host of the podcast who conducted the second date update interview and facilitated the relationship intervention
Jeffrey
Co-host of the podcast who provided commentary and relationship advice during the second date update segment
Quotes
"We notice everything. Yeah. It's a reason why your mom has always known what's up."
Brooke•Early in episode
"You killed both birds, though, is the problem."
Brooke•During confrontation about the ring
"I was going to ask you if you wanted to try it on because the guy was giving me a shitty price for it."
Gage•Explaining his pawn shop strategy
"If I felt looped in on it... I actually honestly think I probably would have. Like a Bonnie and Clyde."
Ainsley•Responding to the ring situation
"So, gentlemen, don't be secretive anymore. Tell your date you want her to help you sell your ex-girlfriend's belongings at the Pawn Store."
Jeffrey•Closing advice segment
Full Transcript
I'm Nancy Glass, host of the Burden of Guilt Season 2 podcast. This is a story about a horrendous lie that destroyed two families. Late one night, Bobby Gumpwright became the victim of a random crime. The perpetrator was sentenced to 99 years until a confession changed everything. I was a monster. Listen to Burden of Guilt Season 2 on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. you get your podcasts. on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Talking to your kids about the dangers of vaping can be hard. Getting them to listen to hot gossip is easy. So here's some drama you could share with your kid. Dude, did you hear about Cassie and Jake? No, but did you hear that vaping can cause irreversible lung damage and nicotine affects brain development? Nuh-uh. You don't need to gossip if you want to have an open conversation about vaping. So if you want to get tips on when and how to talk to your kids, visit TalkAboutVaping.org. Brought to you by the American Lung Association and the Ad Council. I would be dead. Open your free iHeartRadio app, search Between Us, and listen now. All right, brand new second date podcast for you to start your week. Hey, it's Brooke and Jeffrey. Thanks so much for being here. Yay! Today's really a lesson. God, I don't even know if it's that. Like, it's just always shocking to me what people don't tell us before we get the other person on the phone. Oh, yeah. Kind of in general, what men do and think women don't notice. Right! Yeah! Right. I mean, the general rule is we notice everything. Yeah. It's a reason why your mom has always known what's up. Okay? We pay attention. She sees and hears it all. Yes. All right. What do we got for comments? Emmy said, you guys have gotten me through cleaning my room, and that's the toughest chore out there. Not even a 12-hour playlist can do that. Wow. Girl, clean your room more often, and it wouldn't be such a chore. I saw somebody on my stream yesterday doing deep cleaning saying they're watching me play video games and also listening to this podcast. I'm like, how are you multitasking that much? It's like crazy. Double the Jose. I love it. I don't know how. All right. Your brand new second date starts right now. Brooke and Jeffrey in the morning. Second date update. Sometimes for a first date, you need to branch out from doing the same old activities. Oh, for sure. And think outside the box. Nobody wants to think inside the box, Jeff. Yeah, like instead of taking her to a high-end seafood restaurant, take her down to the docks. Hand her a pole and a bucket of worms And see if she can catch her own Seafood dinner Teach a man to fish I get it That's close to the saying I know Give a woman a fish she'll eat for a day Teach a woman to fish She'll smell like clams for an entire week Hey nice That's a good thing One of our listeners has reached out after he took a woman On an out of the box type of date His name is Gage So let's talk to him about it Gage, welcome to the show, man. Hey, how's it going? Oh, did you do some urban foraging to make a salad? In a sense, you're actually pretty close. No way. Do you know what urban foraging means, Gage? Dumpster diving? Yeah, well, that's a more uncouth way to say it. Yeah, sorry, sorry. Instead of us guessing, why don't you tell us about this woman that you met and what you did together? Well, her name's Ainsley, and she is just super-duper cute. We met on one of the dating websites. Okay. And great pictures, great personality, at least online. So we set up a date. Okay, were you thinking in that moment that you wanted to do something unique and special? Or is unique and special what you always do? I kind of almost forgot about it. It, like, really snuck up on me. Oh, no. The way Jeff set it up, it sounded like you were planning something. Well, that's how I thought. I thought this is an out-of-the-box date. You didn't even have a box. This is a scrambling don't-know-what's-happening date. Like, let's just do whatever. So what did you decide to do with Ainsley at the last second? So she messaged me just an hour before to confirm. I was like, oh, yeah, let's meet at this address. So I gave her an address. Oh. Okay. What if you Google the Olive Garden's address and give it to her or what? No, but it was in a strip mall. So there may have been an Olive Garden nearby. Okay. But there's a lot of businesses there. Hey, I'm still in. Like, could it be a mani-pedi at a strip mall? I mean, I'm always down for one of those. We went antiquing. Oh. Cute. Okay. Isn't that cool? Yeah. That is cool. Alexis? I like thrifting, so. Yeah, it's the same. It's just way more expensive. Yeah. Yeah. Yeah. Oh, well. Not necessarily. I think of thrifting as like clothes and antiquing as like furniture So what did you you buy like a desk together or like a Hey oh glassware they have such fun glassware at antique shops Yeah some old lamps Well, an antique lamp, that's hot. You know, there's some really nice pawn shops out there. So the first stop was my favorite pawn shop. You're going to have to tell us where those nice pawn shops are. Yeah, sorry, go ahead. Ever seen Pawn Stars? I took her to like three different places. and she found this vintage scarf that I think was from the 60s that she clearly really liked. So did you buy it for her? Well, I took it up to the front. The guy wouldn't bunch on it. He wanted $15, which is crazy. $15? Bro, you're not haggling for a deal on a date. It was only worth at least $8. I mean, come on. You got to haggle. Haggle's part of the thing. Yeah. Well, you don't want to have a woman see you getting ripped off because that's not attractive either. So I'm glad that you stood your ground and were like, no. What did she say when you didn't buy it? She said it was fine. I think she was impressed. You guys are right. It's an alpha move. Yes. I think she wanted the scarf, but she didn't get the scarf. End of day. I told her she could go back and get it another time if she wanted, but not that day. You can never go back the same day to get that item. Yeah. Because then they'll upcharge you because then they know you really want it. Desperation sets in. Okay. That doesn't feel like very romantic. But that was the first step, right? Maybe he got her something great at another shop. I respectfully disagree with what everybody else is saying in the room. I think you're doing a great job, Gage. So keep going. Yeah, it was fun. And then, you know, we're getting a little hungry because we've been doing that for 45 minutes, an hour. So we popped down to this little local bar and grabbed some popcorn shrimp and had a couple beers. Nice. Popcorn shrimp's so good. Did you talk them down from the price of the shrimp, too? That price was firm, unfortunately. What was the vibe between you two like? It was cool. I mean, shopping was definitely the high point. Once we sat down and we're having some dinner and drinks, it didn't quite feel as natural. The conversation was a little forced at that point. But I still really like her, and I want to take her on a real date now. Oh, like one you actually remember before it comes up? Oh, I see. So not like a last minute date that you just threw together. Maybe even make a reservation. Oh, whoa. Yeah, I'm willing to make a reservation. Wow. You're willing to go that far for this girl after hanging out with her once? She's going to smooth. Oh, yeah. This is the bare minimum Brooke talks about. I know. You made a reservation. I know. You might even propose by the time we get to the end of the call. I'm scared. How long has it been since you last hung out with her? It's been a week and a half. If you were a pro, you'd go back to the pawn shop, get the scarf, and then bring it to the next day. I'm way ahead of you. I went back there to get that scarf. He jacked up the price to $18. So I didn't get it. You didn't get it? Oh, no. No way. So you thought about it. Oh, no. That's just three more dollars. No, he's not willing to budge. And I appreciate that. You know what you want, and you stick to your guns, and you will go for it for nothing less than what you think it's worth. That's what we're going to do with Ainsley here today. Yeah, let's focus on Ainsley, not the crummy shop where I gave a one-star review to. Oh, you reviewed it? Oh, you did. Good man. All right. Well, I guarantee you that our listeners are going to give you a five-star review once we get you a second date. Is this free of charge, or what do I have to pay for it? I like that you're already starting to haggle. I appreciate that about you, Gage. I feel like he needs to pay us $10. We should start somewhere. Yeah, we're going to start at $100 just for him. Oh, wow. We'll meet somewhere in the middle when we come back and do your second date update right after this. Brooke and Jeffrey in the morning. Second date update. I'm not sure if a last second trip to an old pawn shop is what most women would consider a romantic experience. But hey, maybe Ainsley isn't most women. That's what we're hoping for because we've been talking with one of our listeners, Gage, And he admits he did not do much planning before his big date with Ainsley. So they ended up just bouncing around a local strip mall doing some antiquing, haggling over the price of old 1960s scarves, which he never actually bought. So it's been a week and a half, and Gage has now reached out to us saying he would really like a redo where he promises he will definitely do more planning this time around. Yes, he even said he may make a reservation. Whoa Our jaws dropped We never asked him Did you hear anything from Ainsley after the date? Not a thing Oh, okay Well, maybe she's just busy pawning her stuff Like she Her eyes were really open Once you start, you get hooked on it The possibilities Yeah She got the fever Uh-huh Yes You did that, look at you I know, now you have like a shared interest That carries on through the rest of your relationship If we can get her to agree to a second date What if she picks up and she's in a pawn shop? Yeah. Oh, I'm sorry. I'm actually in the middle of negotiating. Can I call you back? Yeah. That'd be so hot. That'd be so hot. That'd be hot. Okay. Wow. This might be a match made in heaven. Maybe it's your pod queen. It could be. Let's see if she even answers the phone. I'm going to dial her right now. Here we go. Hello. Hey, Ainsley. This is Jeff from the radio show Broken Jeffrey in the Morning. Oh, um, hi. Hi. Hi, Ainsley. The whole show's here. Hi, Ainsley. Good morning. I like your name. Ah, thank you. She's like, my parents did well. Yeah. It's unique. We definitely approve, and we don't want to be too intrusive here or anything, but we would like to ask you a few intimate details about your dating life. Oh, my gosh. Nothing too over the top. Why do you say it like that? We don't want the intimate part. Yeah. Just kidding. we do want to pry a little bit, if that's okay. I don know I guess it depends I not sure I just ask do you remember going out a little while ago with a guy named Gage Oh, yeah. Yeah. Perfect. Oh, gosh. The O was sharp. Gage has reached out to us asking if we could get a hold of you, because this is a segment called The Second Date Update. and we're trying to help him figure out if there's a reason why you haven't seen each other in the last week and a half. Okay. So he, wait, he called you guys? He reached out to us and from what we heard, it sounds like, at least from the way you're acting, maybe you don't want to go out with him again, but we don't know if that's true or if there was a problem with the date or with him. And if it is true, we'd love to know why. I mean, I think it's the thing. Would you mind telling us a little bit about your experience with Gage? Sure, I guess. I mean. Only because he's clueless. He doesn't know if something went wrong. Okay. Yeah, yeah, sure. That's fine. Okay. So we'll start at the strip mall. Is that where we start? Yeah. So you know about that. So he gives me this address, which is a strip mall. Did you look it up before you got there or was it a surprise? No, it was a surprise. I didn't know where it was. Okay, so that's. And on a scale of one to ten, how romantic was that idea to you? Well, it was an antique shop, which is, I thought, kind of cute. Like, it's totally different. Never been on a date at an antique shop before. That was new. Was it a pawn shop or an antique shop? I think they went to both. Oh, okay. The first one was an antique shop, which was cute. So we go in and we're like looking around for 10 or 15 minutes. And he's kind of like quirky. You know, he's got this like quirky personality and he's funny. And so you like that. That was a plus. Yeah, I was until he's like, hey, let's go over here across the way. There's this pawn shop over here. Yeah. You can find cool old stuff at pawn shops. Yeah. I had never been to one, so I didn't know. So we go over to this pawn shop, which is very different than the antique shop vibe. Yeah, different vibes. It's huge. It's like, it's very big. It's, you know, I'd never been in one. So I'm kind of like walking around trying to figure out what this place is. Yeah. And he, he's over at the counter and like talking to some guy that works at the pawn shop. And so I realized I've been looking at stuff for a while and he's been talking to the guy for a while. So I'm like, what is he talking about? Like, what's going on? So I kind of like sneak over to see if I can hear what they're talking about because it seems kind of secretive. And I can see that he's got a ring, like a woman's ring, which looks like an engagement ring. Yeah, those get pawned a lot. It's like rings and guns are really what pot shops are for. Why would he be trying to buy an engagement ring? He wasn't trying to buy it. I think he's trying to sell it. Oh. So the guy has the loop and they're looking at it. And it occurs to me that we're not on a date. He's trying to sell his engagement ring. You're running an errand, a really questionable errand. So why didn't you ask him? Why didn't you ask him, what are you doing? What was that? Because if he didn't tell me, that would be weird to ask him. What were you doing over there? Maybe you could position yourself as a potential buyer. How much did they offer? I know Brooke is much more intrusive than most people. She'll just go up and ask any question. Doesn't matter how offensive it might be. Women do need to call out men more. I'm sorry. If your date is pawning a ring during the date, I think you have every right to be like, yo, what's up? Did you just do that? Well, let's just ask him right now, the Brooke way, because he is on the other line, wanting to talk to you as soon as we punch him up. Oh, really? Yeah. Yeah, I think he's there. Gage? He's supposed to be. Hi, Angley. Hi, Gage. So you didn't like antiquing? No. No, I don't. That's what she said. He's trying to not address the situation. Gage, you didn't mention anything to us about a ring at the shop. Look, it belonged to a girl that I did not end up marrying like a year ago. It's like old news. So it was your ring. So you had a year to sell the ring, but you waited until the day of the date to try to sell it? I'm a busy guy. I try to stack things together. I'm going to multitask. If I'm close to the pawn shop, I'm going to take care of business. You just haven't been around the pawn shop in a year. Did you think she wouldn't notice? Look, I was just trying to kill two birds with one stone. You killed both birds, though, is the problem. Okay, well, fine. But, Aangley, are you saying that was a turn-off? It was so weird. And, like, okay, even if you're going to do that, why wouldn't you tell me? or loop me in that that's what we're doing. Well, I was going to ask you if you wanted to try it on because the guy was giving me a shitty price for it. Oh, my gosh. I thought that would be even weirder. Can you imagine? Hey, will you try on my ex's engagement ring so I can get a better price? Well, Ainsley is saying that she just wanted that clear communication so she knew what was going on. Ainsley, would you have done that? Come on. I actually honestly think I probably would have. Like if I felt looped in on it. Oh, like a Bonnie and Clyde. I mean, look, I'm a commitment-minded person. I think that's what that shows. Oh. That is. Yeah. Gage, did you actually sell it? No, he didn't want to offer me anything for it. Of course. I was trying to make enough money for dinner. I didn't want to use my credit card. Oh, look at that. That's a man who doesn't want to go into debt. Also a plus, Ainsley. Yeah. I'm a cash man. Yeah, someone that can think on his feet as the moment comes to him. So we're seeing a lot of positives from this, Ainsley, and we think you should too and consider giving him another chance because if you do, we will offer to pay for your second date. You guys might be a match made in heaven since you are a woman who would have tried that engagement ring on for him. And he still needs to sell it. Or he can hold on to it and use it on you one day I would like to see it You know now I curious about his case in spring Hey look I been thinking about you for the last 10 days and I went back to that pawn shop to get that scarf, but the guy jacked up the price to $18. He was trying to gouge me, so I didn't get it, but you've been on my mind. I'm just asking you, please let me take you out on a real date where I'm not pawning any jewelry. Wow. That is super romantic, Ainsley. We've never heard a man ever say that on this segment. We've done thousands of these calls. But at this point, we do need a yes or no. Do you want to see Gage one more time? Sure. Yes. Hey. Wow. The most hesitant yes we've ever had. Her heart was so in that, Gage. All right. I'm going to impress you. You better. Oh. Oh, this is only a 90% chance that she's going to ghost you before you actually meet up. So good luck. I think so. I'll take those out. Brooke and Jeffrey in the morning. I'm Nancy Glass, host of the Burden of Guilt Season 2 podcast. This is a story about a horrendous lie that destroyed two families. Late one night, Bobby Gumpright became the victim of a random crime. He pulls the gun, tells me to lie down on the ground. He identified Jermaine Hudson as the perpetrator. Jermaine was sentenced to 99 years. I'm like, Lord, this can't be real. I thought it was a mistaken identity. The best lie is partial truth. For 22 years, only two people knew the truth until a confession changed everything. I was a monster. Listen to Burden of Guilt Season 2 on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. podcasts. your podcasts. And how many relationship experts always say, if a man could just communicate a little bit more, it's going to make the relationship that much better? Yeah. Yeah, I mean, that's true. All the time. So, gentlemen, don't be secretive anymore. Tell your date you want her to help you sell your ex-girlfriend's belongings at the Palm Store. Ask them to model that engagement ring. It sounds nuts, but it would have It worked with her. It would have. She would. Yeah. You do that and she will love you forever. That is what I've learned from today's call. I mean, she didn't say whether or not she'd want to cut, though. I mean, if you're going to be the model and you're going to help the sale, I'm just saying there's probably a percentage that should be thrown away. Yeah, yeah, yeah. She was starting to do this. And a cut of money is the start to any healthy relationship. That's right, Jeff. Modern day dating. I love that we're doing this service for the world and all the daters out there. So if you want to get in on this action, email the show. We'll call that person who's not calling you back and go check out all of our second dates. We have them up on our podcast wherever you get yours at Brooke and Jeffrey. I'm Nancy Glass, host of the Burden of Guilt Season 2 podcast. This is a story about a horrendous lie that destroyed two families. Late one night, Bobby Gumpright became the victim of a random crime. The perpetrator was sentenced to 99 years until a confession changed everything. I was a monster. Listen to Burden of Guilt Season 2 on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Listen to by Order of the Faithfuls on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. we're also husband and wife. It makes for some pretty entertaining episodes. Listen to Legally Brunette on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Talking to your kids about the dangers of vaping can be hard. Getting them to listen to hot gossip is easy. So here's some drama you could share with your kid. Dude, did you hear about Cassie and Jake? No, but did you hear that vaping can cause irreversible lung damage and nicotine affects brain development? Nuh-uh. You don't need to gossip if you want to have an open conversation about vaping. So if you want to get tips on when and how to talk to your kids, visit talkaboutvaping.org. Brought to you by the American Lung Association and the Ad Council. I'm Anna Navarro, and on my new podcast, Bleep with Anna Navarro, I'm talking to the people closest to the biggest issues happening in your community and around the world. Because I know deep down inside right now, we are all cursing and asking what the bleep is going on. Every week, I'm breaking down the biggest issues happening in our communities and around the world. I'm talking to people like Julie K. Brown, who broke the explosive story on Jeffrey Epstein in 2018. The Justice Department, through we counted four presidential administrations, failed these victims. Listen to Bleep with Adam Navarro on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.