Trading Secrets - 317. Thirty Minute Thursday: Jason & Kathryn's Engagement Recap + This Week in Pop Culture

Episode Date: July 23, 2026

The boys are back for another Thirty Minute Thursday! Jason and the Curious Canadian recap this week's conversation with Kathryn Hurley, including the behind-the-scenes moments from Jason and Kathryn's engagement and why the episode resonated with so many listeners. They also dive into everything happening in pop culture this week, share a few laughs, and cover the headlines everyone is talking about. Whether you're here for the relationship updates, behind-the-scenes stories, or the latest entertainment buzz, this episode has you covered. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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There's a lot of action here. Catherine and I shared that we got engaged early last week. We did an episode breaking down all the ins and outs of it. Put that out Monday. There's so much to cover with that. There's so much happening in pop culture world. There's so much happening in the finance world. There's so much happening in pop culture meets finance.

From what the World Cup did from economic boost standpoint to the United States. We're seeing all different things happen in the markets. When you hit pop culture, you got business meets pop culture. Nick and O'Landria break up. And there's a whole lot of speculation out there about the fact that they broke up 365 days from when they got out of the villa, which people are saying is that a PR scandal? I mean, when we talk PR, business, money, markets, and personal life, there's a lot to talk about on this 30-minute Thursday.

David, how you do it? How you feel in? And you know what? Where do you even want to start? Yeah. No, I think we have to start as we always do. We have to start by recapping the episode on what a great episode it was. Obviously, like you said, there's a lot to get to on today's episode.

But we got to stick to our guns here. And we got to recap the episode. And the episode was you and obviously the lovely Catherine Hurley, soon to be Catherine Tardick. And have you guys talked about that? Is you taking the name? Is that something, is that one of the things you've checked off the list yet? Have you had that conversation?

You can tell you've had a lot of conversations so far. So have you had that one? We've had that one. And yes, she is, she's taken, she's taking the name. that's great and it's i just commend women who stick to that tradition and and want to do that because my god it's a lot of paperwork and it's just you know they got to deliver they got to be pregnant for nine months and deliver and change the last name i think we got it pretty good jay i just got to say shut out to the woman out there because you guys are way you just got to you got to do

it all and we just got to stand by there and support you so so shout up to that i love that yeah absolutely i mean yeah there's so yeah it's a lot of moving parts with that whole situation a lot of people have a lot of different opinions on it. But yeah, she's going to be Catherine Tardick and excited about everything, including that, and excited about what's coming, man. Yeah. I'm just like, it's like a little cloud nine moment. You know what I mean? Like, I hate to be the one that continues to like gush and be like things are so great because it's not like that in all times of life and all areas of life. And there certainly were times in my life. It wasn't like that for me. And just now it is. And I'm just, it's really,

it's really nice. It's really, really nice. You have to enjoy. You have to glow because you You are so happy. And anyone who is trying to interrupt or isn't wanting to consume your happiness right now, that's okay. That's not a you problem. You're supposed to be in this realm. You're supposed to be sharing your story. And those who want to listen are going to listen.

I'll tell you, for those who listened, like I did it, to this episode, listen. I'm my best friend. I've known a lot. We share everything with each other. Even I was listening to this, painting the picture in my brain. And there's a couple moments where I was like, there's a couple moments where I was like, I was laughing hysterically because I know you so well

and you're not a planner, but when you want to make a plan, you want it to be perfect. And when it doesn't go perfect, I can only imagine you're like just on the fly, making things up as you go, trying to make it perfect. At the end of the day,

like you're a smart guy, right? You're a really smart guy. You'd like to have control situations. when that control slips and you've got to double down on being the smartest guy and make the plan and convince and have it all nailed down before you can execute the mission. Dude, I was dying and I want to get to that in a little bit, but I will start it with where you guys started with. When you said to her 100% from the second that you met her,

you knew it was her, I remember the first time I met her last year, I got that same feeling for you and saw you guys together. And we had a grilled cheese making competition at like 2.30, the morning and like it was she left like an unbelievable little note in the morning like David and Hawks so amazing to me you guys I was like hey this this feels like home this feels so good and then I remember you telling me about the conversation that you had with her at the pizza place in Brooklyn where you said to me you're like dude I got to tell you this like did I is this should I said this should I not have said it and when you were when you reiterated like

now that I have gotten accustomed to you in my life like this isn't ending and for you to share that story with everyone else and for them to hear it. I was like, yeah, this is, this brought me back down memory lane. And again, just just kind of layers on on how happy I am for you guys. And, you know, for you, how does it feel to be able to kind of get all of that out there to everybody? No, it's, I mean, it's, it's great. I mean, I really like the fact that we had that month to just kind of live in our own world for a little bit. And, you know, it's like a lot of my life is shared online, a lot of it's not, right? And so I think just this idea of, I don't, we don't have to be in Europe in this moment and just go blast it out and everything.

Let's just enjoy where we're at. Let's just enjoy this moment. So that was really special. It is always, you know, I was talking to my cousin about this today. But he's like, man, you got just like, how does it feel? It's got to be crazy. You're getting so much love and there's support and like, I'm seeing all these articles and everything. And I, you know, my response to him was like it just, it never, it never actually, that, that whole side of it doesn't get old.

It's still so weird. And that's a weird place to speak from on it. But like, you know, this idea that you share all this news and there's, you know, quarter million people liking and 10 million people now have seen that post. And the five, six thousand, whatever is comments and stuff like that, it's just a, that's a lot. And then it's like you see different headlines and different stuff. And it's a strange feeling when you put out news that you're so excited about. And there's just so much out there.

And there's like, you know, kind of. countless support and love. But then you see also some random news articles will be like they try to take such a beautiful moment and the most beautiful moment, honestly, in my life. And then be like, Jason Tardick proposes a girlfriend after seven months. And it's like, okay, like that's the line you're choosing. And then other outlets and stuff say like really beautiful things and stuff. So that is all so surreal to me. But what matters most is that here at home, we're just like so happy. We got to celebrate my family. We got to celebrate with her family's past weekend. We got to see friends and stuff and celebrate. Obviously, more celebrating to do. And we'll be up in New York here soon.

But I'll go back to what you said and what we talked about. And this idea that she's right. I was trying to figure out if I was going to marry her before I dated her. And she's like, what are you doing? And long and short is like the second we started dating and we fully went all in, I knew there was there was just absolutely no turning back. And the last thing I'll say before I open it back up to you on that topic, the compatibility for her and I is indescribable. The speed at which I would say we just connected, like our souls connected, our brains connected, our hearts connected. I think a main driver that is just pure in the purest form of compatibility, just like you and Ashley, it just all connected. And when that happens, the deeper conversations happen quicker. The insecurities where in previous relationships or lives, maybe you're afraid to put on the table because of judgment. It felt so safe to do. And so it was just so simple and so easy that it's like the absolute biggest no-brainer in the world to me. And we announced and shared that we started dating in December.

It was several months before that that we started actually dating. And yeah, man, life is, life is good. So that was a lot there, but throwing out there. It's amazing. And it should be a lot because you're explaining a whole life's achievement of feelings. And it doesn't just go with that moment of engagement. Like you said, like were you trying to figure out if you're marrying her before you're dating her?

Honestly, probably. And honestly, a lot of people do that at our age when they're single and they're tired of dating. And especially if they've gotten their heartbroken and, you went through a couple heartbreaks leading up to it. The last thing you want to do is invest in someone who maybe at the end, it wasn't compatibility, it wasn't going to work that you didn't have the same interest.

So I think what you experience is actually a lot more common and maybe why a lot of people really resonate with this, because when you get in your mid to late 30s and you're single, people start thinking, am I ever going to get fined the one? Am I ever going to have kids? And they start thinking about what life may look like without that. So to be able to put yourself out there. And your guys's life experience allowed you to have this level of transport.

and honesty and honesty with each other. And that's why it's so beautiful and that's why it's so rewarding. And I think you brought up something that I was going to ask you anyways about like, you know, tabloids bringing up in seven months or with less than a year of dating. Like, what's your immediate response? Because I'll, I'll tell you mine after you tell me yours because fun fact out there, I proposed to Ashley a year after we were dating, almost a year after we were dating. And we actually got married six weeks after I proposed to her. So we got married in the civil service then we had our wedding. COVID killed our wedding. But what's your response? Because I have my response when people used to say, are you sure? How do you know she's the one? Are you sure? What's your

explanation for a short, quote unquote, short timeline, which fuck your timelines. They're irrelevant anyways. It took a lot, you know, from the timeline that we shared, it still took a lot of getting a place of in all in life. You go through all these different chapters of life. And when you, Everyone in life has, you know, learning lessons and scars and things that have happened. And the natural tendency when things are scarred and you've gone through really, really tough chapters with layers, it's very easy to be extremely secure of your heart moving forward. And it's very easy to put up walls. And if anyone here is listening is feeling that going through that or connects to that in any way, I think the biggest thing I would say is trust your gut and understand why you're doing it. And when you're with the right person, they don't want to rip those walls down. They want to understand why those walls are built up. And they want to understand why those walls are built up so that you have the safety to know that in their hands it will never happen ever, ever, ever again.

And so to me, that's the beauty of life. And so I think that's just a little piece of advice I have for anyone. And that leads to the question of when you know, you know, and there's no turning back. And I talked about it on our episode. And it's my heart, my brain, my everything feels so safe. She's got my back. Like we're teammates. She respects me and I respect her.

She's extremely supportive. She's selfless. She's empathetic. And I think, yeah, some of the big things are, it's just like, it takes a lot to be vulnerable with anybody in any forum on this podcast. That takes a lot. With friends, it takes a lot. With loved ones, it takes a lot. And I think, like, the way that she holds that vulnerability I share and held it from day one with such care was so foreign to me.

And so it was just the easiest thing. And I think that all kind of connects to compatibility, living, learning, and being in, you know, in enforcing yourself to be in a position to also receive that, but trusting your gut. So that's a lot there. But that's kind of a long-winded answer to your question, which is a layered question. And yeah, I guess I'll kick it to you. What was your initial thought when you saw that stuff? Well, before my, before I give you my response. I just smile and kind of chuckled to myself when you say that because isn't the most annoying saying in the world when you know you know because while you're looking for it, you're like, fuck off.

Like, shut up. Like that's not a real thing when you know you know. Like there's steps to this. It's an equation. Like you put together the puzzle piece. And then all of a sudden you get the answer. It's like, no, man. The first day, after Ash and I's first kiss, I went back to Hawkshouse.

I said, I'm going to marry this girl. Like you said, you know, when you know, you know, it's so true. and it does make me smile because I remember going through your last heartbreak I remember you were calling me and trying to put the pieces and find out why and I said Jason you will know because you won't

have to call me and ask me about these types of things. You'll just know and now like hearing you say that it makes me feel really happy I think at our age when I was in my mid-30s when I got engaged to actually it wasn't early 30s I just said

it was like once you go through the seasons, the full calendar year with someone, you know what you're getting yourself into. You've gone through birthdays, you've gone through Christmas, you go through Thanksgiving, you go through summers and winters, you've met their families, you understand their traditions, you understand your traditions. At that point, like, it's just plug and play. Like essentially, like you know what you're signing up for. They know what they're signing up for. For me, after I experienced everything, I was like, this is a family I want to be a part of, she want to be a part of my family. That was really easy. But yeah, I just think when you know, you know,

And the last thing I'll say, and then I want to get into the actual engagement. And you guys referenced it too. I always said to when people were like, how did you know, like what separated Ashley from everybody else? And I was like, when you think of marriage and you think of engagements and these fun moments, you think of the fun moments with a lot of different times in your life with different partners. But what you're saying, what you've said this whole podcast of what I felt with Ashley and continued to feel is she's the first person in my life I ever wanted to go through all the bad moments with. because marriage is hard and life is hard. And when you have a friend that passes,

when you lose your job, when you have a financial crisis, when their family needs you to take care of them, when your family needs her to take care of them, when someone gets sick, when someone, who's going to be there? Who's going to really be there?

Who can you look to and be like, I want to go through that moment with you. And if I didn't have you in that moment, I would be fucking lost. That is Ashley was the first, and she is ride or die lawyer. like she teaches me more about that every single day with how she is. So that for me was like those two things like calendar year and that moment,

but it's just it's just the truest thing ever. So if you're out there and you're happily married and you know this feeling and if you're not, I'm telling you, it will be that simple one day. You just got to keep self-improving and you got to keep loving yourself and you're going to track what you project out there. Yeah,

I think you nailed that. I love your advice, by the way. I think it's so damn good that. that when you think about your partner in life and you close your eyes and think about some of the worst things that could happen in your life or some of bad moments you've already had and you think about what would my experience be and who would I turn to. If that person's not at the top of your list and you can't even imagine how you'd get through it without that person, I think that's something

to think about. And I think that's perfectly said. And I also like the way that Catherine positioned the two on the podcast, which is like so, oh, it's so refreshing. It's so, it's just beautiful. And it's, it's so true, not just for relationships, but friendships. Those who continue to spew hate, those who continue to talk poorly about other people and, and just constantly run their mouth, right? You know those people in your friend group. We all have them. I could tell you right now, friends that are acquaintances and people that are in the friend group that when I get with them, it's judgment on everybody, talking shit about everybody, this person's doing that, this person's doing that.

And it's just like when when you turn around and you're not at the table, you know it's going to be said about you, right? And I think that having someone and friends and loved ones where they say you remind me of that person and you think like that's awesome, that's hilarious, that's great. That is a compliment. Wow, that's endearing. that's such a great sign of connection, love, and respect. You know, like if I took a golf tee shot or made a big putt and had a celebration and

someone's like, oh my God, you remind me a David. I'd be like, yeah, you're right, you're right, right? We can do that a hundred times. Someone says like, oh, you remind me or your mom or you remind me a Catholic, what Catherine said on the podcast. It's just, it just hits home. It hits home and it's so real and it's so true. Love it.

Well, that was a good little in the weed session. Always feels good to chop it up with that. let's go to the actual proposal because that was the meat of the episode and i got to say jason when you said you had this perfect plan everything was set you your description of this bag like i was thinking about this like the bag that you had and i'm just like laughing to myself and like picturing you like awkwardly holding onto it but you thinking you're not awkwardly holding onto it when you said jason that the photographer was 45 minutes late. To me, it was like in such a weird,

such a, you got the bag, you're bringing the bag. Dude, when you told me, oh, there's the bag. There's the infamous bag right there.

Yeah, that thing's not discreet. Here's the little area. This is, oh, it's not discreet. And she checks all these little pockets all the time. And this was the pocket.

Because I could see the bulge here. And I needed to make sure that it was still there. So I always like, so that's why I kept this thing. This was like, shit right here. That's so funny. Well, listen, I got to say, when you said the photographer was 45 minutes late, and that's what kicked you into, like, panic.

I got to get a beer. I got to go to overdrive. I got to get it. I was laughing so hard on the inside because how many times have I chirped you about being late? I've chirped you so much about being late. And when you were saying that, I was literally, I have an ear. I'm like, this is sick, beautiful karma. This is a huge win for David because you've been late so many fucking times.

and I've told you when you've asked you're like what's one thing I can tell? I'm like, you got to start being on time. And when I heard that and to hear you panic and that made the story for me, man, when you started like glitching out basically and like getting the text. That's a perfect way to put it, right? Glitching out. Because you know me like the one thing like, oh, all right, I do need to be better about beyond time.

You're right. And that's hilarious. That's very ironic. But the one thing that like kills me is like even more than being late, it's incompetence. Right. So like I'm, but I'm always planning ahead for incompetence because I've dealt with it a lot. And I'm thinking, okay, guys, like on my way, I'm literally like telling the concierge or the people at the hotel, please, please make sure like when we get in this hotel room, it doesn't say congrats anywhere. Don't have the champagne out.

Don't have anything that would surprise it, right? Photographers, videographers, you got to be hiding, you know? Please be on time. Like just the smallest shit. Hey, guys, this is a surprise, right? And you could imagine just like, I'm trying to keep my cool. and then the videographer is 45 minutes late and I'm trying to have to delay it then in that 45 minute period she starts catching on then I'm having to have Evan call from the massaged booth while he's getting massage having their best I'm throwing that shit over and then like okay that's behind us had a couple drinks it's behind us we're going to walk out we're going to walk out thankfully she's like I go to the bathroom and it's like when you walk into a cruise ship or I'm like a red carpet like eight employees like greeting us walk down the aisle what do you guys do it so she's in the fucking bathroom. I'm yelling at them. Guys, go. Like, stop. Be discreet all while trying to keep

my composure, ready to snap at any point. And it takes a lot for me to snap. Then we get down there, and they tell me that spot. And then I turn and she literally says, the photographer's right there. I'm like, you got to be. At that point, I'm like, you just got to wing it. And at the end of the day, you, you keeping your composure is not like a normal person keeping your composure. Like you, you don't keep your composure very well. You don't snap, but like, you can tell. Like, it's on your face. And getting that text from her friend was great, but it also probably put you in panic driver, like, oh my God, this is slipping. Like, this is an actual sign that, like, I'm starting to blow it. And so you had to, like, speed up the pictures that you shared on the, on the real. I said to

you, you're looking out and you're looking out and getting a silhouette of yourself. And in one hand, you're thinking, okay, take a breath. I'm going to do this. And the other hand, you're looking in the ocean and be like, how me sitting here taking a silhouette, looking to the Mediterranean was not part of the plan. Well, how the hell did we get here? I was, there was a moment, dude,

when I was looking out there and I'm like, what are we doing? Like, how am I actually getting to the end goal here? Like, am I ever? Like, what am I just not doing it? Was there ever a point where like, I just can't do it right now? Like, this is just, it's too far gone. This meme,

Dude, that is the funniest meme. It's like it's literally you at your engagement. Just trying to wait for it. But there was a point where I'm like, do I quit? Do I just quit and be like, hey, babe, this is what I was trying to do it. It totally didn't work. But I knew the boy, I always tell the boys. I'm like, I talked to John Padgio.

He called me last time. Like, here's the part you're going to love. And every time the guys just love that stuff. Because the photos make it look like you nailed it. Oh, yeah. Looks like I crushed. She fell to her knees. Meanwhile, she's going to a bathroom.

She's like, Jason's being fucking sketchy. He's got this goddamn bag. It's glued to him. I just wanted to get a tissue out of it. He slapped my head. It's like, then when she talks about in the pocket, this guy's never asked.

She's like, part of his job is to like literally put stuff out online about his life. He's never asked me. And all the time I've known him to take a photo of him. And always like telling me to take a photo of a silhouette. Like, what the hell? And I love how you're like,

oh, you like had to check it out. And be like, this is sick. Like, you got to get in there. She's like, R.A. Jason. No, I thought that was great. You guys did mention you nailed down three spots, Nashville, Michigan, Cabo.

Is there a leader in the club host? Do you have a personal preference? Anything? Do you have a timeline? Do you have a year? Do you have a month? What do you feel in here? I mean, first and foremost, 100% 2027. Like, it's not even, it's like the 100%. If we go to a courthouse and get married, we're getting married in 2020. Yeah. That's happening. Where are we a leader, man? I would say Vegas odds. Let's call it.

Let's call Vegas odds have us at 65% Nashville. Okay. Yeah. 30% Cabo. Yeah. Let's go let's go 5, 10% Michigan. Maybe 8% Michigan, 2% other. But no, those odds will change.

Trust me, those odds will change. Yeah. Right now, here's one of the problems I've realized is that for anyone that's planned weddings or your kids have planned weddings or you're planning your wedding, I have learned something real quick. Everyone, of course, wants to talk about it. Fair. I love it.

And I'm here to talk about it. The problem is when you start to share the updates of the decision you're making. So like we're making, like we're in it. We're getting ready to go. Like we're in the process. Like we're vetting different wedding planners and Florida. Like we're doing it. You then have like a direction you're moving.

And then you immediately will get feedback. from those people you care, respect and want to hear from it. And then it changed. So like going into probably the last two times we saw our family, like it was going to be Cabo for like Cabo, 100%. Then like after talking to her family and my family, like I think we're back on Nashville. So when you start to share like all the details, you get all the opinions and I try to sway your opinion based on the feedback you're getting.

And then it becomes like a zigzag. So I think it's going to be more of like we're going to just do less sharing and just decide what we want to do. And that's and that's how you should do. and you can't make the date around certain people. You got to just choose it and people will make it a priority and they'll come. I love Nashville for you guys because I think there is an element of like being home and being able to, there's so much going on, being able to like have home base for each other as like a support system

and like not have to like worry about someone hosting your being in a foreign spot and like packing a bunch of shit. Like I couldn't imagine packing like a bunch of stuff for like a different like a destination wedding. but I will say the best part about destination weddings, as you've seen, and you kind of mentioned it, like, that would give, like, if you have the wedding in Nashville for myself, like, let's just say I wouldn't get to know, not that it's anything about me, but I think you guys would want this.

Like, I would not probably get to know Catherine's family that well if it was in Nashville. Just because, but if you go to Cabo, it's a destination, you're all at the same place, you're hanging by the pool, you're getting drinks together. You have, like, those weddings I've been to, you come away with such a stronger, feeling of who they're marrying.

Like, their roots of that. Like, no matter what, I'm going to be by your side up there, loving it. I'm so happy for you and Catherine. But to get the full feel of it, it makes people walk away so much better. But there's also, like you said, difficulties with family members and getting everybody to a destination like that. So you guys will do fine. I'll never forget my mother-in-law.

I propose on a Friday. You flew into town. We had a little party Friday. We had a party Saturday. Monday, we went out for dinner. And we were like, wasn't that great? She brought out this big folder. and she's like, you guys are so far behind in the planning process.

I was like, Brenda, I just got proposed on Friday. She's like, we need to figure out date and venue and where we're. So you'll see. I think the thing that I'll say is like first three months, last three months, first three months, you get a lot. There's a lot of work to do. You got to get the band. You got the photographer.

You got the planner. You get the venue. Take a breath. And then the last three months is like, oh, shit, it's go time. It's making sure that you got the details lined in. You start doing them with the seating chart. You start doing like the day of and the planning and all. that stuff. It's good. I mean, I think that's really good advice. First month, first three months,

last three months. I think it's really good. And it's just go, go, go. Only thing I would say, I agree with you on, like, you're making me see this is part of the thing. You put it out there and then people make you think. I think you're right. I do agree on the fact that like you would bond more in Cabo. That's for sure. I think if we did it in Nashville, we still would 100% do full Fledge welcome party. Full Fledged Sunday because 93% of the maybe 95% maybe 98% of people at the wedding, it will be a destination of. Yeah. No one's not many people would be living here. That's true. Five percent. So you kind of have to set it up like a destination wedding. But yeah, either way, no matter what, listen, it's going to be fun. It's going to be great. We're going to have a good

time. That's the best. We got a lot, dude, and we got a bachelor party. I know we talked about last week. Yeah. Bachelor of plan. We got a whole lot of action. We got a whole lot of action.

We've got a whole lot of time spent on that. It was worth it. We might have to hit the overtime button here a little bit because we got a rifle off a couple things here that are happening in the pop culture world. Should we turn the page here? Yeah, we got turned the page. We already said at the start. There's so many things happen in the pop culture world.

I've been itching. I've been hitting the group chat for trading secrets to talk about these things. Should we stretch it? Should we do it? Should we push overtime? What do you thinking? I think, you know what? We got too much to cover in too little time. This was a hot topic. You know, this is a special one. So we'll keep this to the 30-minute Thursdays. We won't go overtime. Next week we'll cover it all. We'll cover it all. We're going to cover some of our favorite celebrities that we're seeing in ways that we couldn't. Tom Brady, he's everywhere. We've got to touch on Jenae, my girl, Janay and Kenny and all.

That will still be in the news next week. So we're going to hit that. We're going to talk about the the breakup, the Love Island breakup of Alandria and Nick. And we're going to talk about all these little things that in the city just closed out. They had their reunion. They're still Amanda and they're still Kyle. Oh my God. It's blowing up. This is 30 minute Thursdays.

I'm just going to take this thing all the way to the house right on 30 minute. True of the world. We'll see you next week. We're going to take a little step back of the Jason Marriage Talk. We're going to dive into what we're talking about on the podcast. We're going to get in the weeds. We're going to talk to pop culture. We're going to talk gossip. We're going to talk money. I'm fired up. I will see you next Thursday. 30 minute Thursday. Take that, Jesus. Bye.

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