Armchair Anonymous: Bad Proposals

Summary

Armchair Expert with Dax Shepard
Episode Summary: Armchair Anonymous: Bad Proposals
Release Date: February 14, 2025
Host: Randall Shepherd and Monica Lilly

---

Introduction: Setting the Stage for Bad Proposals

The episode opens with Randall Shepherd and Monica Lilly introducing the theme of "bad proposals," framing it as a series of stories where well-intentioned marriage proposals take unexpected and often disastrous turns. The hosts express both amusement and empathy as they prepare listeners for the chaotic proposals shared by their guests.

Monica Lilly:
"Yes, it was meant to pair up a little bit... Happy Valentine's Day."
[00:47]

---

Cole's Proposal Gone Wrong

Guest: Cole, a chemical engineer from Billings, Montana, shares his tumultuous proposal experience.

The Perfect Plan Falls Apart

Cole recounts his meticulously planned proposal, intended to occur on New Year's Eve during a ski trip to Park City. He describes his efforts to keep the engagement ring a secret by sending it to his parents' house for safekeeping. However, unforeseen logistical challenges arise, leading him to scramble to retrieve the ring without his fiancée discovering his plans.

Cole:
"We are supported by Tropical Smoothie Cafe... Prepare for love at first sip."
[02:28] (Note: This timestamp appears to be part of an advertisement and is likely misplaced in the transcript.)

Technical Troubles and Miscommunication

As Cole attempts to set up a camera to record the proposal, technical issues plague his efforts. A deceptive phone call offers him a fraudulent solution, adding to his stress. Despite these setbacks, he proceeds with the proposal, which initially elicits a hesitant response from his fiancée.

Cole:
"Wait, aren't you glad that you screwed it up yesterday?"
[12:25]

The Snow Drift Incident

Seeking redemption after the rocky proposal, Cole organizes a hiking trip. However, his decision to speed up his Honda Accord leads to the vehicle becoming stuck in a snow drift. Stranded in freezing temperatures with limited supplies, the silence grows tense until Cole's fiancée comments on the mishaps.

Cole:
"We got married on December 29th. Just celebrated our first year of marriage."
[12:59]

Randall Shepherd:
"Cole, do you recognize? You're an interesting mix of brilliant as hell and dumb as fuck."
[11:25]

Despite the chaotic start, Cole and his fiancée celebrate their first year of marriage, reflecting on the challenges they overcame together.

---

Olivia's Harrowing Proposal Experience

Guest: Olivia from Las Vegas recounts a harrowing proposal that turns into a life-threatening robbery.

Ambitious Plans Under Strain

Olivia and her boyfriend, who had been together since high school, decide to get engaged amidst personal and professional pressures. Olivia describes her boyfriend's intense planning to create an elaborate proposal, aiming to impress with a memorable experience.

Olivia:
"We were going to move back home... got really rough."
[38:18]

The Robbery Turned Shootout

At the jeweler's store, just as Olivia is about to receive the engagement ring, two armed robbers burst in. What was supposed to be a joyous moment devolves into chaos as the situation escalates quickly. One robber threatens her while the other begins a shootout, resulting in Olivia being accidentally shot.

Olivia:
"I was looking at your phone location because you just stormed out of the house... thinking maybe I need to work on my anger because of this."
[48:10]

Randall Shepherd:
"Do you resentful at the jeweler for escalating it to a gun battle?"
[49:50]

Aftermath and Reflection

Miraculously surviving the ordeal, Olivia reflects on the trauma and the emotional scars it left. Despite the severity of what happened, she expresses no bitterness towards the robbers, acknowledging the surreal nature of the event. The episode highlights her resilience and the enduring bond between her and her wife, who stayed by her side through the ordeal.

Olivia:
"I think overall I'm just glad I'm alive... I'm still not gonna even get close to that. I'm good."
[50:26]

---

Additional Stories: Jessica and Rob

Jessica's Story:
While Jessica's detailed narrative is less prominent in the transcript, she briefly shares her experience, which involves a humorous twist during a proposal setup, showcasing the unpredictable nature of such events.

Rob's Story:
Rob discusses a failed proposal attempt that involved an intense mountain hike, illustrating the lengths some individuals go to create the "perfect" moment, often ignoring their partners' comfort and desires.

---

Insights and Takeaways

Throughout the episode, the guests' stories underscore the unpredictability of proposals and the importance of considering the other person's feelings and circumstances. The hosts and guests reflect on lessons learned, emphasizing that even well-intentioned plans can go awry, highlighting the need for flexibility and genuine communication in relationships.

Rob:
"The big lesson is if you don't listen in life, it gets bigger and bigger... life forces you to change."
[31:28]

Monica Lilly:
"Love that."
[51:12]

---

Conclusion: Embracing Imperfection in Love

The episode concludes with reflections on the shared experiences of the guests, celebrating their resilience and the love that ultimately prevailed despite the disastrous proposals. The stories serve as a testament to the unpredictability of life and love, reminding listeners that imperfections often lead to the most memorable and meaningful moments.

Randall Shepherd:
"It's memorable for sure."
[32:23]

---

Notable Quotes

• Cole:
  "If that's what he was trying to say? I powered through it."
  [10:22]

• Olivia:
  "Everyone makes a joke. It's like a blood diamond... I had to go, yeah."
  [51:09]

• Randall Shepherd:
  "You're the first person we've talked to who's been shot."
  [52:36]

---

Final Thoughts

"Armchair Anonymous: Bad Proposals" delves into the complexities and unexpected turns that can accompany marriage proposals. Through candid storytelling and heartfelt reflections, the episode highlights the importance of authenticity and adaptability in relationships, offering listeners both entertainment and valuable insights into the human experience of love and commitment.

---

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Transcript

[Randall Shepherd]

Wondry subscribers can listen to Armchair Expert early and ad free right now. Join Wondry plus in the Wondry app or on Apple Podcasts. Or you can listen for free wherever you get your podcasts. Welcome, welcome, welcome to Armchair Anonymous. I'm Randall Shepherd. I'm joined by Monica Lilly.

[Monica Lilly]

Oh, that was cool.

[Randall Shepherd]

It was hard. Okay. The prompt was bad. Proposals, proposals gone wrong.

[Monica Lilly]

Yes.

[Randall Shepherd]

But oh my Lord. I mean, this is like tied with that crazy bear attack or shark attack. This goes some places.

[Monica Lilly]

It really builds.

[Randall Shepherd]

This one, it just gets. Gets more and more intense.

[Monica Lilly]

Yeah.

[Randall Shepherd]

And then the last one is a nail biter.

[Monica Lilly]

Wow.

[Randall Shepherd]

Wow. This is a banger.

[Monica Lilly]

Yeah. Please listen to this one. And happy Valentine's Day.

[Randall Shepherd]

Oh, is that what it is?

[Monica Lilly]

Yeah, it was meant to pair up a little bit.

[Randall Shepherd]

Okay, great. Yeah. Happy Valentine's Day. May your heart be full of love and merriment. In his name we pray he has risen.

[Monica Lilly]

What are you gonna do for Valentine's Day? Eat chocolates?

[Randall Shepherd]

I'll try not to.

[Monica Lilly]

Yeah.

[Randall Shepherd]

I mostly think of my mom always would ask me to be her Valentine.

[Monica Lilly]

Oh, that's sweet.

[Randall Shepherd]

Yeah. And so I'll. I'll ask the girls to be my Valentine.

[Monica Lilly]

That's cute.

[Randall Shepherd]

And they're. They'll still like it.

[Monica Lilly]

They'll oblige.

[Randall Shepherd]

Yeah. Did your dad ever ask you to be his?

[Monica Lilly]

Course not.

[Randall Shepherd]

Yeah. Did you guys do Valentine's?

[Monica Lilly]

We didn't even have it. Yeah, well, we did. My mom. No, my mom would sometimes.

[Randall Shepherd]

Would you get you a box of chocolate? My mom would get us a box of chocolate.

[Monica Lilly]

I think she would do something nice every now and then.

[Randall Shepherd]

But I'm not going to get my kids anything because they're already spoiled. They already have two.

[Monica Lilly]

Why don't you tell them that you're getting you anything?

[Randall Shepherd]

You're going to repent this Valentine's Day. Please enjoy bad proposals. We are supported by Tropical Smoothie Cafe. February is the month of romance and to celebrate, Tropical Smoothie Cafe is remixing a classic with their fan favorite chocolate covered strawberries smoothie. Featuring a delicious blend of strawberries, dark chocolate, white chocolate, banana and non fat yogurt, this crave worthy flavor is only available for a limited time, limited edition. Yes. In app and online. Prepare for love at first sip. And if you're a fan of their tropic bowls, make your taste buds swoon this Valentine's Day season with their new Nutella drizzle. Add on. There's just something about chocolate that says romance. Isn't there?

[Monica Lilly]

There sure is. Chocolate's done A great job marketing to lovers.

[Randall Shepherd]

Absolutely. This month, gift a loved one or be your own valentine by indulging in refreshing tropical goodness. Because at Tropical Smoothie Cafe, it's always tropic time. Order ahead, take the scenic route and earn rewards with the Tropical Smoothie Cafe app. Download it today. Visit tropicalsmoothi.com to find a cafe near you. We are supported by the second season of the hit Apple TV comedy series Shrinking, which critics are hailing as one of the best new comedies on tv. An AFI television program of the year, this highly lauded comedy is both hilarious and poignant. The stellar ensemble has been nominated by the Screen Actors Guild as an outstanding comedy ensemble. Starring Jason Siegel, Jessica Williams and, oh, not to mention the legendary Harrison Ford. Also nominated for a SAG Award for outstanding comed, Shrinking follows a grieving therapist who ditches the therapy rule book to dish out unorthodox advice to his clients. What could possibly go wrong? Shrinking is now streaming on Apple TV plus, and you can learn more at apple tvplus.com Hard times come and go Good times take them slow My life, I had them both Remember one thing, you gotta.

[Cole]

I'm gonna keep on shining Cole. How you guys doing?

[Randall Shepherd]

Good. Can you hear us?

[Cole]

Yeah, I can hear you guys. Can you hear me?

[Randall Shepherd]

Yes. Where are you, Cole?

[Cole]

All right. I was really worried about the sound quality, so hopefully it's all right. I am in my closet here.

[Randall Shepherd]

Sound is dynamite. Connection is a little iffy. Are you far from your WI fi? Because we might have to piss Monica off and get you out of the closet.

[Cole]

I'm through four doors. I can go in a different room here.

[Randall Shepherd]

Now we're getting a nice tour of your home.

[Cole]

I can go to the home office here.

[Randall Shepherd]

Somehow got worse. I hate to say that.

[Monica Lilly]

So I was right.

[Randall Shepherd]

We've lost the visual of you. Can I ask one last thing? Would you be willing to go to that first room you walked into? Because it was dynamite in there.

[Cole]

My wife is getting ready for work here.

[Monica Lilly]

Oh, sorry.

[Randall Shepherd]

Our apologies. Sorry. Now we've got great image. We've got great sound. Hi. Tell her we say hi.

[Cole]

She's stressed. She says hello.

[Randall Shepherd]

All right, now we're talking. Cole, where are you?

[Cole]

I'm in Billings, Montana.

[Randall Shepherd]

That explains the spotty WI fi.

[Cole]

Yep. This story may or may not involve some other spotty cell service areas.

[Randall Shepherd]

Okay, great. Are you from Billings?

[Cole]

No. So I'm originally from Stroudsburg, Pennsylvania.

[Randall Shepherd]

What brought you to Montana?

[Cole]

Work.

[Randall Shepherd]

You're a strong man. You've got broad shoulders. Are you doing something physical?

[Cole]

I am not. I'm actually a chemical engineer, but I do work at a refinery.

[Randall Shepherd]

Are you lifting incredibly heavy test tubes all day?

[Cole]

That's right. I load them up with the lead and all the other heavy things.

[Randall Shepherd]

Okay, great. Cole hit us with this bad proposal.

[Cole]

The bulk of it is in Billings, Montana. I've lived here for about four years now. I was proposing my girlfriend at the time, just to give a little bit of backstory, met on New Year's Eve, very High School Musical. We like to kind of think that we're a little Troy and Gabriella. Every New Year's Eve, after we kind of celebrate our anniversary, we both like to ski. So we'll go up to the mountains and make a whole weekend out of it. Flash forward to March of 2021 and I'm thinking about proposing I buy the ring. But I'm planning the proposal and I want to get engaged New Year's Eve. The whole plan is we're going to go to Park City, we're going to ski, we're going to have beautiful time in the mountains. It's going to be gorgeous. Proposal, get engaged.

[Randall Shepherd]

I love it.

[Cole]

Fast forward to April. We now are moving houses. I don't want her to find the ring as we're packing up all the boxes. I actually send it to Pennsylvania to my parents house. I'm young, so I just kind of pop it in a little manila envelope and let usps kind of do its thing.

[Randall Shepherd]

Oh, wow. Cole, you're a bright man. You're a chemical engineer. I think keistering it during the move would have been preferred to that.

[Cole]

I'll tell you what, it made it there, no problem.

[Monica Lilly]

Oh, that was a red herring.

[Cole]

But now fast forward to October, November. We've kind decided to make it a big trip. I suggested it because I wanted to have our friends and family there. And that way it could kind of be a big celebration after the proposal. The issue is that all my friends and family could go and were on board and none of her friends and family could go at all. I have all these group chats going with my friends and she gets really sad. So I start thinking, well, she's going to be real sad if I propose and none of her friends and family are around. This is when I kind of start wanting to audible here. The issue now is that I don't have the ring.

[Randall Shepherd]

Right? Right.

[Cole]

So now I have to call my parents because originally we were going to go home to Pennsylvania for Christmas. I was going to pick the ring up. I thought I had the Perfect plan. So now I have to ask them to ship the ring back through the mail. So now they put it in another vanilla envelope, ship the ring back through the mail. I can't send it to my house because she might open it. So I got to send it to a friend's house now. So I'm receiving this thing again. The ring gets here unscathed.

[Randall Shepherd]

Usps, Whatever it is. Good job.

[Cole]

So now I adjust the plan a little bit because we live in Montana, beautiful state, about an hour away. There's like a nice mountain near us. So I plan a little weekend that we're going to go to that mountain. So it's Friday morning of the engagement weekend, and I'm texting in this New Year's Eve group chat and I sent a text that's like, hey, I'm going to get engaged this weekend. You guys happy for me or what? And the next thing I see pop up is Tess was removed from the group chat.

[Randall Shepherd]

Oh, no.

[Monica Lilly]

She was on.

[Randall Shepherd]

Oh, Jesus.

[Cole]

One of my friends had added her in to the group chat because she was so upset that she wasn't being included in these plans. And the next text I get is, what the hell did you just do? And I look at my phone and I'm at work and I just scream, oh, no. Everybody's dead silent. So I work kind of in a high risk business, so everybody thinks something really bad happened. You could hear a pin drop because we've had really bad days. My boss comes over to me and he's like, what the hell just happened? And I kind of tell him, and he says, go home and I don't want to see you until Monday. Get your sorted out.

[Randall Shepherd]

Oh, oh, good boss.

[Monica Lilly]

That is a good boss. But he was upset.

[Cole]

Yep. So I got about four hours until she gets home from work. I'm doing the whole nine. You know, I'm getting flowers, I'm getting chocolates. I'm trying to set everything up at home. And then I remember she wants it recorded. So I go and I try and set up the camera. My video on my phone is not working.

[Randall Shepherd]

Oh, boy.

[Cole]

Quick troubleshooting. Find the first number for a remote Apple support. Call it. And they're just like, you know, we can fix this problem. It's going to cost about $250. If you download this screen sharing app, we can really see what's going on here. So I download the scre sharing app. Then they say, we just need a wire transfer. So all you got to do is open up and log into your bank.

[Randall Shepherd]

Oh, no, stop it.

[Cole]

So I go in, I got the screen sharing app. I open up my bank app. And then it all hits me. I'm just like, I'm getting scammed right now.

[Randall Shepherd]

Yeah.

[Cole]

I hang up on the guy immediately. He calls me back. He's like, what happened? I was like, oh, yeah, you wanted 170, right? He goes, yeah, yeah, 170. I was like, you said 250 before hang up again.

[Randall Shepherd]

Now, I'm smarter than you.

[Cole]

I'm wise to it. So thankfully I avoid getting scammed at any point.

[Randall Shepherd]

Do you think the Lord is telling you to not get married to this woman?

[Cole]

If that's what he was trying to say? I powered through it.

[Randall Shepherd]

Oh, God. Good, good.

[Cole]

Finally, she gets home. I propose to her. It was good. And she kind of looks at me and she goes, I really appreciate it, but I really want to see how you were actually going to propose. So I get another chance of redemption. Saturday morning, early, we load the car up. It's December in Montana, but we're going hiking. And so we get about 10 miles out of cel. We're about a half mile from the trailhead. I can see the trailhead in the car, and I hit a little snow drift. So the first one car kind of moves a little bit, and I see a second one coming up, and I say, you know what? All I need is a little more gas. I'm driving my Honda Accord cross tour, so I give it a little more gas. We barely squeak through the second snow drift. And then I see a third one coming up, and I think to myself, you know what it worked best? A little more gas is all I need. I speed that thing up and I beach the car on a two foot snow drift, totally immovable.

[Randall Shepherd]

Cole, do you recognize? You're an interesting mix of brilliant as hell and dumb as fuck.

[Cole]

I would say that's spot on. I think my friends would describe me as the smartest person they know with the absolute least amount of common sense.

[Randall Shepherd]

Okay, that works. More of a PG version, but yeah.

[Cole]

So now we're beached in. The Honda is 15 degrees out. I got about a quarter tank of gas, usually prepping for the winter. Winter in Montana. I got my blankets, my snow shovel, my emergency kit, just in case. I have not done that this year because it was a mild winter. All I have is a snow.

[Randall Shepherd]

Oh, that's not gonna help.

[Cole]

I tell my fiance. Wait in the car. So I spend the next about three hours in small gloves because I wasn't planning on doing significant work with a Snow scraper digging out the car.

[Randall Shepherd]

This is miserable.

[Monica Lilly]

Do you think she was like, I don't want to go through with this?

[Randall Shepherd]

She must be thinking, there's a lot of red flags.

[Cole]

I'm worri at this point. Now get the car unburied, four floor mats under the wheels. Get it out of this snow drift, start driving back. And we are driving back in absolute silence. My fingers are numb. I'm bloody. And finally, she kind of looks over at me. She's like, you know what? One day this will be funny. But right now, aren't you glad that you screwed it up yesterday? And all I could just say was like, oh, boy.

[Monica Lilly]

Oh, wow.

[Randall Shepherd]

Oh, yeah. That's a rough start.

[Monica Lilly]

But can only go up from there.

[Randall Shepherd]

That's a good silver lining.

[Cole]

We got married on December 29th. Just celebrated our first year of marriage.

[Randall Shepherd]

Congratulations. You went through hell and high water or high snow to get there. Cole, you're a delight. This gal, as shitty as the proposal was, is a lucky woman.

[Monica Lilly]

And we got to meet her. We didn't even realize.

[Cole]

I did not tell her that I was going to try and commandeer the closet. And she comes in at like 1:40 and she's like, what the hell are you doing? I'm getting ready for work. I got to go. It was very high stress at the beginning of this.

[Randall Shepherd]

High stress. Feels like it might be status quo.

[Cole]

These are not. Not really abnormal situations for me, unfortunately.

[Monica Lilly]

Oh, this is great.

[Randall Shepherd]

It's a delight meeting you. Thank you for telling us that story. We're so sorry you went through all that.

[Cole]

Great to meet you guys. And my college roommate Matt and his wife Courtney, they got me into listening to the podcast, and they are super up on the prompts, and they sent it to me, and they're just like.

[Randall Shepherd]

You gotta thank them for us. All right. Great meeting you.

[Cole]

Nice to meet you guys. Thanks.

[Olivia]

Hi.

[Randall Shepherd]

Is this Olivia? Yes.

[Monica Lilly]

Look at your sweater.

[Jessica]

Just for you guys. And my earrings?

[Randall Shepherd]

Cherry to the max.

[Monica Lilly]

For a second, I thought they were tattoos. When I just first glanced, I thought they were your arms.

[Rob]

I did too.

[Jessica]

No cherry tattoos yet. I have an orange and a peach.

[Monica Lilly]

Oh.

[Randall Shepherd]

Oh. So that would go perfectly into your fruit aesthetic.

[Jessica]

It would.

[Monica Lilly]

You're in a legit sound booth.

[Jessica]

I'm at my brother's house. He does voice acting, commercials and stuff. As soon as I got the email, I was like, I need the setup help.

[Randall Shepherd]

Get out of there. I don't care what audition you have. Are you in California?

[Jessica]

No, I'm in Syracuse, New York.

[Randall Shepherd]

Oh, okay. He's doing voice work up there. That's interesting.

[Jessica]

Remotely.

[Randall Shepherd]

Nice. Okay, so you have a bad proposal story.

[Jessica]

Since you guys started doing anonymous. I was waiting for this prompt. I said, when this prompt comes out, I am locked in. They're gonna pick it. And everybody in my life is like, like, please don't get your hopes up. There's millions of people that listen. And I said, no, this is it. May 2017. My boyfriend and I had been dating for like five years. We're talking about getting engaged May 1st. We go look at rings. I pick out a ring that I love. I know he buys it that day, even though he makes me wait outside. So after May 1st, I'm on high alert. Nails done, dressed up anywhere, we're hanging out. I'm looking good. I'm ready to go.

[Monica Lilly]

That's right.

[Jessica]

This is our proposal. May 15th. He says, we're gonna go out to dinner, wear a nice dress. I'm gonna pick you up. And I'm like, okay, it's gonna happen. So we start driving. He's driving past all of our regular spots. We're starting to get into some weird back roads and unfamiliar territory. After about 40 minutes in the car, he starts to slow down. I see a sign on the side of the road that I recognize. Trail of terror.

[Monica Lilly]

What the fuck?

[Jessica]

This is where he and I had our first date.

[Randall Shepherd]

Can you tell us what the trail of terror is?

[Jessica]

There's a huge open field, which in peak season is packed with people. People are drinking, people are having snacks. They're hanging out with their friends. There's a big projector playing scary movies. And then in the far right corner of the field, there's a trail that goes through the woods that you pay to get a ticket. And you walk down and they jump out and scare you.

[Randall Shepherd]

It's like a haunted trail year round?

[Jessica]

No, this is just an October thing. So we had our first date, like, the week before Halloween 2012. So to the right of the field, it's not a haunted house, but it's like a trailer connected to a barn. They makeshift at a haunted house. So that's a separate attraction, but basically an empty lot, dirt parking lot, nobody's there. We pull in. I'm like, it's our first date. This is where it's gonna happen. But I am oldest daughter Virgo, notorious rule follower, don't like to take risks. I'm not not a trespasser. He is the opposite. He's youngest son. He's like, whatever, let's go. There's no other Cars. There's no sign of life in this place. It's the middle of May. It's a beautiful sunny day. So he leads me out into the middle of the big field and he's holding my hands. He's looking at me. We're chatting and I know it's about to happen. I'm letting it sink in while still being like, I'm afraid of getting in trouble. As we're chatting from the tree line, away from the trail, away from the barn, we hear a voice going, hey, what the fuck are you doing here?

[Monica Lilly]

Oh.

[Randall Shepherd]

Oh, no.

[Jessica]

We're like in our sappy moment and we look over and this man, bucket, hat, sunglasses, shotgun, starts charging at us. No, I've told you kids, get the fuck out of here. No trust acting. And I'm like, I knew this was gonna happen, but I'm panicking. I'm like, sir, I'm so sorry. We're leaving right now. And he's like, absolutely fucking not. This is not happening again. And I. And like, this is how I'm about to die and my parents are going to find out that I trespassed at Haunted Trail and that's how I was murdered by this man with a shotgun.

[Monica Lilly]

Yeah, he wants to make an example out of you too.

[Randall Shepherd]

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[Monica Lilly]

What a cast. I'm so excited to watch this.

[Randall Shepherd]

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[Jessica]

The guy goes, this is the last time this is happening. Come on boys. From behind us in the haunted trailer slash barn, we hear the garage door open and hear chainsaws.

[Monica Lilly]

Are you kidding me?

[Jessica]

Out comes these people with masks like clown scary. The guy with the gun is charging one way at us. The clowns are coming the other way at us. We're surrounded in the middle of nowhere. Nobody knows where we are.

[Randall Shepherd]

This is a horror movie.

[Jessica]

I'm kind of laughing cause I'm so nervous. Like I'm having fight or flight. Freeze, I guess.

[Monica Lilly]

Yeah.

[Jessica]

I look at Paul. He doesn't look nervous about them. He's like afraid of me in the moment. They all click.

[Monica Lilly]

He did not.

[Jessica]

Did you do this?

[Randall Shepherd]

Oh, I wasn't there. He planned it.

[Jessica]

He was totally in on it.

[Monica Lilly]

Oh my God.

[Randall Shepherd]

That's spectacular.

[Jessica]

He kneels down and pulls the string out. We're still surrounded.

[Randall Shepherd]

Oh, pity pictures.

[Jessica]

It's so scary.

[Randall Shepherd]

Oh, yeah. I'm glad you sent pictures because this is really a hard to believe. Oh, my God. And you're now, I would imagine husband has. Yeah, they're very scary masks. For anyone that thinks these were like Amazon.com masks. No, these are atelier bespoke masks. Your husband has the most nervous laugh smile on his face looking at you.

[Jessica]

So he reached out to the trail of terror and said, hey, this is where we had our first date. I know it's your off season. Do you mind if we just come on the property so I can propose? And they're like, absolutely. And then the guy sends a message like an hour later and is like, do you want us to scare her? And sends this whole plot for how they would scare me. And he was really unsure and finally was like, we could do like a light scare. Like thinking that they're gonna pop out somewhere. Like, the gun was not mentioned. Oh, my God. Threatening of our chainsaws. He's got the ring out. I feel like I blacked out. Like, I really don't remember this, but I know that I plucked it out of the box and I started walking to the car. I was so pissed. I was like, I'm taking my ring. I'm getting the fuck out of here.

[Randall Shepherd]

Yeah, no party. You liked it, right?

[Jessica]

No. He's like laughing. He's like, wait, wait, wait, wait, wait. And I turn around, all the clown people start taking their mask off. Two of the scary people are our super good friends that are photographers, and they captured the whole thing. So that's how we have the pictures.

[Randall Shepherd]

Do you start thawing as you see it's your own friend.

[Jessica]

Yeah. And they brought a bottle of champagne. She had it ready. And then I started to relax.

[Monica Lilly]

That is so funny.

[Jessica]

It was really scary.

[Randall Shepherd]

Yeah. What does that group of folks do between October and the following October?

[Jessica]

It's so funny because the guy who sent the whole plot that works at the trail, he's like, I'm gonna see if I can round up some guys. Larry's got volleyball tonight or whatever. Like, they're just normal dudes. But he's like, my scarers are around. They're just jonesing to scare some people.

[Randall Shepherd]

Yeah.

[Monica Lilly]

And is your life fun like this?

[Jessica]

He is so fun.

[Monica Lilly]

A I love.

[Jessica]

We have two little kids now, and I still pick on him for this. And he's like, it's so special. But, like, I was traumatized for a bit, but I wouldn't trade it. Obviously. I got to Talk to you guys.

[Randall Shepherd]

That's one step away from choreographing a car accident. Like, you get T bone and then the ambulance comes in. It's your mom and dad. And they've got look.

[Monica Lilly]

It's memorable for sure.

[Jessica]

My friends that took the photos and videos, they did our wedding too. So they made this whole beautiful wedding video. And at the end, he has the footage of the proposal. And so loud and clear at the end, I say white guys with guns are my biggest fear. If it was just a clown, I'd be like, okay, weirdo. Yes, I'm scared. But the man threatening my life really took it to another level.

[Randall Shepherd]

Really ups the stakes in a hurry.

[Monica Lilly]

You were right to know this would get picked.

[Randall Shepherd]

Yeah.

[Monica Lilly]

I don't think we're going to have a story like this.

[Jessica]

I really have a feeling. I'm so glad he is here. And also my siblings are here. If they could just peek their heads into the sound booth.

[Cole]

Hi there.

[Jessica]

Hi. This is the husband.

[Randall Shepherd]

You have the most adorable, nervous smile in all those photos. Like, is she going to get over this? Oh, my gosh.

[Monica Lilly]

I was worried what a swing you took.

[Olivia]

I know. I didn't intend to do anything scary. But he was just so passionate about it and so excited. And he was like, I'll get my crew.

[Monica Lilly]

That's a nice thing you did for them.

[Randall Shepherd]

Yeah, it made it fun.

[Jessica]

We love you guys so much. Squeezing into the boat.

[Monica Lilly]

You guys are so cute.

[Jessica]

You.

[Randall Shepherd]

It's delightful to meet you guys.

[Monica Lilly]

To meet you all first.

[Jessica]

So happy Liv got to tell her story. It was hysterical.

[Randall Shepherd]

Yes. Unbelievable. I was completely on the hook. Did not see it coming. Monica got it. She was a little ahead of me.

[Monica Lilly]

A little ahead. It took a while, though.

[Randall Shepherd]

It was great.

[Jessica]

It was so lovely to meet you guys.

[Randall Shepherd]

Yes, you guys too. Take care. I went into a whole, like, I totally believe these crazies live in that barn. Lady.

[Monica Lilly]

I could have gone that way. How would I?

[Randall Shepherd]

You would.

[Monica Lilly]

Well, you don't know.

[Randall Shepherd]

I don't know. You're right. But when you get scared, I mean.

[Monica Lilly]

I would be crying, right?

[Randall Shepherd]

Yeah.

[Monica Lilly]

So then I. Maybe I would be crying, but I would also cry.

[Randall Shepherd]

That would be nice. That'd be nice.

[Unknown]

Which would you rather happen? The proposal on the Jumbotron from last week or this?

[Monica Lilly]

I would rather this.

[Randall Shepherd]

Yeah. You wouldn't be hated then. You're surrounded by love, family and friends and champagne. All the stuff they wanted. Is it to get through this other part first?

[Monica Lilly]

I mean, I guess. Then you really hopped up. Adrenaline is up.

[Randall Shepherd]

Aroused.

[Monica Lilly]

You're aroused?

[Randall Shepherd]

Hop in the back of the car.

[Monica Lilly]

Maybe that's a fun evening you're feeling. Life is so short.

[Randall Shepherd]

Get the chainsaws going in the background. Oh, hi. Hi, Jessica. Where are you?

[Rob]

I'm in Texas.

[Monica Lilly]

Ooh la la. Where?

[Randall Shepherd]

What part?

[Rob]

Fort Worth.

[Randall Shepherd]

Do you grow up there?

[Rob]

Yes, but I 18, flew out of here like a bat out of hell into Colorado.

[Monica Lilly]

Oh, okay.

[Rob]

So I was in a relationship. It was serious. We lived together. He made content in the Rocky Mountains for a ski resort. He ended up taking a job in Salt Lake City for an even bigger ski resort. He comes to me and says I have to hike this mountain facing the big mountain ski town that he works for to get content of stargazing. So he has to get a shot at midnight of the ski resort. So we have to hike up this really intense mountain starting at dusk. It's going to be four hours hours to go up. I'm complaining about this. I'm like, I don't want to do it. I understand why I have to do that.

[Randall Shepherd]

Yeah, we just go up there on your own and get the fucking shot and then come home.

[Rob]

Well, apparently has to go with somebody because it's dangerous. I'm just hemming high. I'm like, I don't want to do this. And he's like, no, please, this guy can't come with me. I need you to go. I'm being pretty whiny here.

[Monica Lilly]

No, you just have a boundary.

[Rob]

I mega learned boundaries from this whole situation over many years time. Then we even do a test run the Sunday before. He's like, we need to practice this because this is a huge hike. And so we're hiking up this mountain. I'm just upset the whole time. The next week comes along when it's time to do this important night shoot where they're going to have the whole resort lit up. Turns out there's a storm coming as well.

[Randall Shepherd]

Oh, geez.

[Rob]

So we get to the trailhead at dusk and I'm complaining about it still. And he stops and he goes, please, if you ever just do anything for me the rest of your life, please just do this.

[Randall Shepherd]

At any point are you getting the least bit suspicious?

[Rob]

It's only when he said that, but my mind went to, there's no way that he's going to do this when I have made it clear I don't want to go on this hike.

[Randall Shepherd]

This is not my dream proposal situation.

[Olivia]

No.

[Rob]

And if you knew me, you know I'm not wanting to live in the mountains. He's like, I have to do this. It's dangerous. Someone has to come. And so I'm finally just given. We get to the top and all I do is collapse on the ground.

[Randall Shepherd]

Ground.

[Rob]

I'm in fetal position, feeling sorry for myself. And he's setting up this camera on a tripod. And all of a sudden he's like, please, please, just come over here. I just need one thing from you. And so I forced myself to get up. I walked past the camera and I could see, actually it was really beautiful. The stars. There's lightning in the distance, by the way.

[Randall Shepherd]

Oh, wonderful.

[Rob]

You're at the top of a mountain of a really difficult hike. I go walk over in front of the camera, and he drops down on one knee and he opens a little box and it's lit up. And I see this glimmering, sparkling flower ring. And the first thing out of my mouth was, no, no, no, no, no, no, no. Not now, Please not now.

[Monica Lilly]

Oh, yeah, this is tough.

[Rob]

I must have blacked out the rest. I just have a flash of. I know now I have to go down this mountain with this storm and pendulum. The moment that is supposed to be so special.

[Randall Shepherd]

You're walking into your shared future together. The other thing is, if I'm this person, I want a sincere yes. That's what I'm in the market for. I don't want anything coerced. Like people who ask people to marry them in front of huge crowds. I'm like, don't they realize the person kind of has to say yes? And in this case, even if you wanted to say no, you're like, I'm gonna say no, and then we're gonna be on a four hour hike in the middle of the night on this.

[Monica Lilly]

I mean, you did say no.

[Rob]

Oh, that's the funny thing. I look back now and I never said yes. But it was an assumed yes.

[Randall Shepherd]

Right? Not now. It means like later. Yeah, yeah, yeah.

[Rob]

I'm just crying. And we get down the mountain and we have this hotel room, had champagne and chocolate covered strawberries. I just remember crying in the hotel. And I think he said something like, I just thought that once it would happen, you'd be happy.

[Randall Shepherd]

Probably picked the wrong girl for that whole exercise because no.

[Monica Lilly]

She said so many times, no, no.

[Randall Shepherd]

I know he wanted the gal we talked to who is a riverboat guide. He's picked the wrong partner for what he wants to do. Oh, shit. Are you guys happily married? You're not married.

[Olivia]

Okay.

[Randall Shepherd]

I got panicked. You held up your hand like, oh, fuck, you're happily married, but you know, like you're given signs the whole time. You want someone that wants to hike up to the top of this mountain.

[Rob]

Definitely. That's true. But I think more than anything, he wanted the photo.

[Monica Lilly]

Uh huh.

[Rob]

I think he had a vision in his mind if I want this photo. And even if the intention was, is.

[Randall Shepherd]

Good, it was a little murky.

[Rob]

I had to learn a lot. We both did, obviously.

[Randall Shepherd]

So what happens when you're in the hotel room and you're crying?

[Rob]

We go to bed because we're so codependent. We're obviously getting married.

[Monica Lilly]

Oh God.

[Rob]

We're not gonna break up.

[Monica Lilly]

That's insane.

[Randall Shepherd]

That's too scary.

[Rob]

The next day, he posts the picture. This is it.

[Cole]

Oh, wow.

[Randall Shepherd]

It's beautiful. He was onto something with the photo. So at first I was like, that's so cute. He figured out how to light the ring from the box so you could see it up there. But now I realize, no, no, that was always gonna be a part of the photograph.

[Rob]

Yeah. And we were together for like two years and I couldn't plan the damn wedding. And then it imploded. You know the big lesson of if you don't listen in life, it gets bigger and bigger and bigger until life forces you to change.

[Randall Shepherd]

I think in those situations, their subconscious figures out how to get them out of it if they themselves can't. You end up having an affair, something materializes, your subconscious saves you somehow.

[Monica Lilly]

The bottom will fall out at some point.

[Rob]

Yeah.

[Randall Shepherd]

Well, thank God it wasn't post marriage and kids. Yeah.

[Rob]

I'm so grateful for all of it, genuinely.

[Randall Shepherd]

And did he find an outdoorsy gal?

[Rob]

I have no idea.

[Randall Shepherd]

Okay, fair enough.

[Rob]

I hope so.

[Randall Shepherd]

Yeah. Here's a question. In your analysis, looking back, what was it that you think he represented that you had decided, oh, I'm supposed to be with someone like this? Like, what story did you have? Why was he the person you were supposed to be with at that time?

[Rob]

Well, I fell in love immediately. You know when you meet someone and it's like, whoa. All of your childhood stuff is brought up immediately because it's so intense.

[Randall Shepherd]

Yeah.

[Rob]

Immediately I knew my life had changed forever. And now I know that's usually a red flag.

[Randall Shepherd]

Yeah, right, right.

[Monica Lilly]

Yeah.

[Rob]

It was just a mask. I think for me to remain really comfortable, to not put myself out there and I could kind of hide. It was very codependent that that ending shot me into deep emotional intelligence over time. Because to have the kind of life and love that I want has forced me to Grow immensely.

[Randall Shepherd]

Do you think it's possible that when someone has great dreams and aspirations, but they have some fear preventing them pursuing them, and then they meet someone who's already so clearly on a trajectory that just folding into that feels like a great way to not have to confront those fears?

[Rob]

Absolutely. I mean, I. I just didn't have internal backbone of like I'm whole within myself and I've had to learn that incrementally over time. I was learning that through that relationship, even getting to that relationship, I had to grow tremendously to even be in it. So everything was perfect. There was no time wasted.

[Monica Lilly]

Yeah.

[Randall Shepherd]

Well, good. And you got a really beautiful photo out of it. I mean, there's no arguing. That's a gorgeous photo. Yeah.

[Rob]

I mean, I hadn't seen it in many years.

[Randall Shepherd]

Sure. Could be on National Geographic traffic.

[Jessica]

Yeah.

[Randall Shepherd]

I'm glad no one died on this hike. A nighttime hike.

[Monica Lilly]

Struck by lightning.

[Rob]

Yeah. Well, it's so funny to me that there are all these impending dangers like falling off a cliff or being struck by lightning, and the real danger was the proposal.

[Monica Lilly]

Yeah, exactly.

[Randall Shepherd]

Well, Jessica, thanks for sharing.

[Olivia]

Yeah.

[Randall Shepherd]

Lovely meeting you.

[Rob]

Thank you.

[Randall Shepherd]

Take care.

[Rob]

Bye.

[Randall Shepherd]

We are supported by Nordic Naturals. I love that name. Let's just start with the name. Nordic Naturals.

[Monica Lilly]

Great name. I also love these products.

[Randall Shepherd]

You're in love with them?

[Monica Lilly]

Yes. I already went through an entire magnesium.

[Randall Shepherd]

You did? You blasted through?

[Monica Lilly]

I blasted through. And a vitamin C. Well, did you.

[Randall Shepherd]

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[Monica Lilly]

And it functions, it's pretty, it's effective.

[Randall Shepherd]

It'S efficient and highly functional.

[Monica Lilly]

Yes.

[Randall Shepherd]

Head to squarespace.com for a free trial. And when you're ready to get started, go to squarespace.comdax to save 10% off off your first purchase of a website or domain. That's squarespace.com dax to get started today.

[Unknown]

I'm going to text you guys photos for the next one. Don't look yet.

[Monica Lilly]

Don't look.

[Randall Shepherd]

I'm getting my phone.

[Monica Lilly]

Don't look.

[Unknown]

Ready for Cole.

[Randall Shepherd]

Hope it's Cole again.

[Olivia]

Hello, can you guys hear me?

[Randall Shepherd]

Oh, beautifully, Cole. You're our second Cole today. And. And we don't generally have Kohl's.

[Olivia]

Really?

[Randall Shepherd]

Yes.

[Olivia]

Okay, I love that.

[Randall Shepherd]

Where are you at in the country?

[Olivia]

I am in Las Vegas, born and raised.

[Randall Shepherd]

Oh, wonderful. Okay, so you have a bad proposal story and we're dying to hear it.

[Olivia]

It is a pretty wild story. So buckle up for this one. I'll set the scene a little bit. My girlfriend and I, we had been together since high school. So we were high school sweethearts. Arts. We were going to the University of Utah for college and we were in our junior slash senior year. We're kind of that new norm of five year senior. We were living together and full intention of getting married and everything like that. Just still wanted to finish out school and we unexpectedly got pregnant.

[Randall Shepherd]

Okay, congratulations.

[Olivia]

A little bit early. Still wanted to kids and I was so close to getting my degree and I loved the University of Utah. It was really important for me to get my degree there and then we were going to move back home. It's where all of our family is. She really wanted her mom to be there when we had our first son. I was kind of naive when I graduated and I Don't know if it was a little bit of arrogance or just being naive of like, yeah, I'm going to move back home. I'm going to get a job. It's going to be easy. They're going to see University of Utah. It's a pretty decent business school. And I moved back home and I just could not find a job.

[Randall Shepherd]

What year was this?

[Olivia]

This was 2018. I had made a promise to my girlfriend. I was like, all right, by the end of the year, we are going to get engaged. But once again, this was with that naive intention of, I'll have an entry level job. I'll be able to start saving. I'm going to be living with her mom. We'll have the opportunity to save up some of those funds. And then I got a recruiting job. Job at a Bed Bath and Beyond E commerce center.

[Randall Shepherd]

Oh, okay.

[Olivia]

And all I had to do was recruit people to work there for the holiday season. And as long as you didn't murder people, you got a job that was only supposed to be there from October to December. And I had done a well enough job that they were like, okay, we'll keep you till March. And it was approaching the end of the year. I still had this pressure to get this dang ring. And I'm working all this overtime and busting my tail with all the pressure there so that I can meet this goal. Now it's like a goal for myself. Instead of this wonderful woman and mother of your first child that you've been with since you were 15, this is also for her. It was like this personal stretch for me to get to the finish line.

[Randall Shepherd]

Yeah, you're either gonna be a failure or not based on this arbitrary goal.

[Olivia]

About a week before all of this happens, the job after telling, was gonna be there till March. They were like, we're not gonna be able to do this. We're so sorry. You've crushed it. But they just aren't gonna let us keep you here unless you wanna go work on the warehouse floor. And I was like, I don't think I'm prepared for that. I am super low. This year has gone really rough. And I call my mom. We go to this Marie Callenders that's across from a jeweler. She's like, I'll help you with the financing of this ring. You made a promise. We love her and we know you love her, so we'll help you out. And I'm like, cool. Part of me still doesn't feel right. I'm still just doing this to Meet a goal, because I want to be able to have the elaborate dinner in that moment, and I get to share all of my heart. And now it's kind of turned into, let's get this ring. You're going to do an impromptu proposal and just be like, trust me, we're going to have a good life. I love you to death. I'm going to finish this promise. We pick out the ring, and next week, they're like, come back. We'll have all the pieces together. We'll put the finishing touches. We go in the morning, we finish it out. And they're like, all right, come at 4:45. Store is going to be closing, and we'll get you set up. The piece I've left out so far is this jeweler was in a terrible part of town. My mom wasn't going to come this time, so it's just going to be me. And I show up and there was another couple there. I'm just waiting in their lobby until they're ready to call me up. Once I go up, showing me the ring, it looks amazing. All that fear and kind of extra stuff I was worried about went away. Because now, at the end of the day, I do get to marry my best friend, mother of my child. It's amazing. And then out of nowhere, I would say the length of this is maybe 40ft or so. Two robbers walk in, both in ski masks, and it's guns raised. Everybody get the fuck on the ground. Don't move. One guy jumps over the display and starts heading towards the back. There's two owners that are up at the front ones kind of dealing with the billing and closing out for the day. And the other's with me, and the other thief is heading towards us. My hands are up now, looking back like, there's no way this is happening.

[Monica Lilly]

Yeah.

[Randall Shepherd]

And does it cross your mind, I don't care what they steal, but don't steal this ring?

[Olivia]

Oh, I think it was more than that. Yeah. It was like, is this it? He then directs me to go behind the counter now. And all I could think of in the moment to respond was like, please don't kill me. I have a feeling. And then he's like, all right, get down on the ground. And everybody thinks this is a weird part when I tell the story, but he was like, this will all be over soon. And it kind of made me feel relieved.

[Monica Lilly]

It did. Because to me, that could mean, I'm gonna kill you. It'll be over.

[Randall Shepherd]

It says a lot of things to me. It means okay, there's a human here. They want me to know my suffering's gonna be over soon. I wouldn't think he's gonna kill me. I would think he's letting me know we're gonna be in and out. This is something very human about that.

[Monica Lilly]

Taken.

[Olivia]

I think I'd be closer to you, Dax. Him responding in general gave me a little bit of just weird comfort because what he does next is then zip tie my hands.

[Randall Shepherd]

Oh, wow. These are like pros.

[Olivia]

Yes. We find that out later as I'm down there. Genuine near death thoughts. Am I going to ever get to see my son again? I'm seriously not going to get to marry my girlfriend. Like, I'm not going to get any of this. And then a tad bit of how is this my fucking luck? We're going to make you lose your job. And then let's do this to you.

[Randall Shepherd]

Just strong armed robbery. Let's throw that on from the back.

[Olivia]

Long time jeweler for them. He was like a Venezuelan war vet. He is peeking around the corner with a gun.

[Randall Shepherd]

Now, you got to consider a shootout.

[Olivia]

And consider I did. Because they see him after he's poked his hat out a couple of times. And that is when the shooting starts.

[Randall Shepherd]

No, there is a shootout.

[Monica Lilly]

Stop it.

[Olivia]

And it is a tight enclosure. There's a reason they have you wear headphones when you are at a gun range or anything, because it is loud. This whole ordeal feels like 30 minutes. I've seen the video because I had to go to court for it. All this stuff, I mean, it plays out over like four and a half minutes. And so the shootout might have been 10 seconds or so. And then it just stops. And then I feel somebody tugging at my back. And I turn around and it's one of the robbers isn't saying anything. And I'm thinking he's trying to maybe mug me and leave.

[Randall Shepherd]

Oh, I'm thinking he's gonna use you as a shield. He's got to get you up.

[Olivia]

I think he was trying to prop himself up because all his motor functions are going at this point. Because he got shot. Oh, several times. And he's on top of my legs, so I'm also trapped. And so I'm looking back and I'm going, what do you want? And then his gun discharges in me.

[Randall Shepherd]

No. What?

[Olivia]

And so he shoots me on accident.

[Monica Lilly]

Where on you?

[Olivia]

Right in my side. And I actually shared some pictures. I sent them over.

[Monica Lilly]

Oh, my God.

[Randall Shepherd]

Mamma mia. It's not a graze because it definitely entered. But you can see it entered and exited.

[Olivia]

Did it exit at least some shrapnel.

[Randall Shepherd]

Boy, thank God it was aimed just that inch to the right, because they didn't get any intestine or anything, right?

[Olivia]

Nope. And everyone that I work with now in a medical background, and my friends that are in medical background, they're like, do you know just how lucky you are that he was not off by a couple centimeters? And I was like, probably don't want to play that what if game, because that's what kind of messes me up a little bit. But, yeah, so he shoots me. It's the full spectrum of panic, fear, potential shock. I have, like, one shoe on at this point. My wallet and my phone are, like, sprayed across the room. And I could, like, see all the blood off my phone.

[Randall Shepherd]

Oh, wow.

[Olivia]

And I tried to stand up, and I was like, just no possible way. And so I inch over to this cabinet to kind of, like, prop myself up, and I'm just holding the wound. It felt like time had stopped. I mean, I'm looking straight ahead, and there's a dead guy that I had to crawl out from under.

[Monica Lilly]

Oh, my God.

[Olivia]

The dust kind of settles. I'm focused now, looking down at the wound the whole time holding it. I tried to, like, slowly pick my sweatshirt off of my skin. And I mean, it's, like, sopping. It's stuck. It hurts. I've been seeing these videos lately. You know, like, people doing the grip machine, and they're squeezing as hard as they could. It feels like somebody is doing a grip machine on that spot. And the burning is insane. That's why on the pictures, you can see. See, it's like, black. That's a burn. Then the police come in. They had to, like, cut all my clothes off in the store on the gurney, and I'm butt naked in a jewel right now.

[Rob]

Oh, my.

[Olivia]

Granted, I'm covered, but still.

[Randall Shepherd]

There's one last thing, sir, before we get you to some medical treatment. It's got to embarrass the fuck out of you for a minute.

[Olivia]

Exactly. And so now I'm on the way to the hospital. My uncle was a firefighter. My dad's a firefighter. And so I'm cracking jokes about the city fire department versus county fire department. They're probably thinking, like, this guy is insane. He's potentially going to die. And they're jabbing me with the IV and everything, and the ambulance is moving. And so I'm in the hospital now. They're like, all right, we're gonna take you up for a CT scan. They were looking and they said, okay, so where you got shot, it would be way riskier for us to do surgery to remove shrapnel than it would be to just let it be pushed out of your body over time.

[Randall Shepherd]

Right.

[Olivia]

It was not critical now. And so that kind of brought me some comfort. And then my girlfriend shows up and it was was like, surprise.

[Randall Shepherd]

Oh, I bet she thought it was so sweet though. She's already worried about you. And then you look at her and you say, I was there to get a ring. That's very sweet.

[Olivia]

She was like, I was looking at your phone location because you just stormed out of the house. You didn't say anything. You just said, love you, bye. What am I going to say? Hey, on the way to get something really nice for you, she's like, I was looking at your location. And then it just stopped at the hospital. My mother in law thought I got like in a bad road rage accident. And so I was like, maybe I need to work on my anger because of this.

[Randall Shepherd]

Who all got hit? You? The one robber who was on top. You died.

[Olivia]

And then the jeweler got shot a couple times too.

[Randall Shepherd]

The guy that was shooting the gun.

[Olivia]

Yep. He shot and got shot and then the robber died from his shots. And then the other robber took off.

[Monica Lilly]

Wow.

[Randall Shepherd]

Oh boy.

[Monica Lilly]

Wow.

[Randall Shepherd]

And did they ever find the other robber?

[Olivia]

They did. And it was wild cause I ended up having to testify, but I had never seen that guy's face. I could point out the other guy's eyes, at least from his mask. So I'm up there, I have to recant my story, then just say, I don't know this guy though. But they had planned this for weeks. They were jail mates in Florida. They had been pinging their phones and saw that there was like a thousand texts and calls over the past couple weeks. I think that couple that was in the store earlier, they thought was probably the last customer instead of me.

[Randall Shepherd]

Right.

[Olivia]

And so when that couple left, they're thinking, okay, we're good, let's get in here.

[Randall Shepherd]

Are you resentful at the jeweler for escalating it to a gun battle? I hate to be judgmental of anyone when I wasn't in that situation, but I feel like they could have maybe just gotten out with all the jewelry and no one would have been in the emergency room.

[Olivia]

I think overall I'm just glad I'm alive. People thought I would be angry and bitter towards the robbers, and honestly I'm not. Maybe they were in a circumstance that Made them feel like they had to do that. That's unfortunate. People say, did it give you this newfound look on life? I think probably yes. But it didn't give me, like, why did he shoot and why did he do this? I made it out alive. It's a crazy story, but I didn't have as much anger towards him for that because I don't know what I would do in that situation. I was not one of those people that, now that this happened to me, I'm gonna go get a gun. I was like, I'm still not gonna even get close to that. I'm good.

[Randall Shepherd]

Well, unfortunately, the fact that the jeweler had the gun is kind of what led to all the shooting. I can't imagine those guys were trying to get murder on top of robbery for no reason. Reason.

[Olivia]

Maybe that's also why when he told me, this will all be over soon, that's why they zip tied me and just were trying to do a smash and grab, and then it turned into a shootout. Yeah.

[Randall Shepherd]

Dude, that is wild.

[Monica Lilly]

Oh, man, I'm so glad you got out of there.

[Randall Shepherd]

Did they get the ring?

[Olivia]

The robbers didn't. It was a botched robbery.

[Monica Lilly]

They didn't get anything.

[Olivia]

My ring stayed intact. No issues with it.

[Randall Shepherd]

It doesn't give you PTSD when you see it on her fingers.

[Olivia]

No. Everybody makes a joke. It's like a blood diamond. I would actually get mad she wasn't wearing it because it was like, do you know what? I had to go, yeah.

[Monica Lilly]

Did they give it to you for free? They should have at least done that.

[Olivia]

So at first they weren't, but I think it's because they didn't know the extent of what happened. And then everything as it came out, they were like, we got it.

[Monica Lilly]

Yeah, that's nice.

[Randall Shepherd]

That feels like a minimal gesture when.

[Monica Lilly]

They'Re in Marie Calendar's got you a couple free meals.

[Randall Shepherd]

Oh, that cheese soup they make?

[Jessica]

Delicious.

[Olivia]

That Marie Calendars isn't even there anymore.

[Cole]

Oh, well.

[Randall Shepherd]

Yeah. There's shootouts across the way. I would have shuttered it as well.

[Olivia]

We were married five years ago. And then we added another child as well, so. So there is a happy ending to this.

[Randall Shepherd]

Okay, good.

[Monica Lilly]

Love that.

[Randall Shepherd]

Just meeting you. You don't deserve to go through this like this should happen to me because I'm always sticking my nose into things.

[Olivia]

I wouldn't wish it on my worst enemy. I'm good now because it's six years removed, but that first year, you look in the mirror every day and it's just right There. And the scar kind of used to be gross because it would keloid. It's now and then.

[Randall Shepherd]

Nightmares. Any nightmares?

[Olivia]

Not really nightmares, but I would be, like, overcome with emotions sometimes. I remember one time we were just eating dinner and I just start bawling. I actually work on the same street about a mile away from where it happened. And so for the first four and a half years that I drove to work, I would take a different location so that I didn't have to drive past it all the time because obviously I had to go to therapy for it.

[Randall Shepherd]

You're the first person we've talked to who's been shot.

[Monica Lilly]

I wasn't expecting it. In a proposal story, I'll tell you.

[Randall Shepherd]

Oh, yeah, it's a real left turn.

[Olivia]

I'll give a shout out to my wife. She definitely wants to come in. Please.

[Randall Shepherd]

Yeah, bring her in. Hi.

[Jessica]

You want to see the blood diamonds?

[Randall Shepherd]

Oh, the blood. Beautiful rain. Yes. Wow.

[Olivia]

So, yeah, she was the biggest armchair fan. Everything that she brought up, she'd be like, oh, I heard this on armchair. And then she finally made me listen when we go on our road trips and she would play the fart armchair anonymous. That one's hilarious. And then she was like, if a proposal prompt ever comes up, you have to tell it. And so it came up, and I didn't know, but I was just like, I'm gonna say this. And let's see.

[Cole]

Wow.

[Randall Shepherd]

Well, it's a slam dunk.

[Monica Lilly]

Hard to beat.

[Randall Shepherd]

Yeah, yeah, very hard to beat.

[Monica Lilly]

Well, you guys are so cute.

[Randall Shepherd]

Yeah, we're delighted that you listen. Thanks for indoctrinating your husband to us.

[Jessica]

Yes, I'm spreading the word. Can I just quickly shout out my best friend in Germany? She just had a baby and she's a big arm cherry. So I wanted to shout Jordan out.

[Randall Shepherd]

Jordan, shout out, Jordan, shout out.

[Monica Lilly]

Congratulations on the baby.

[Randall Shepherd]

All right, well, lovely meeting you guys. Lovely meeting you.

[Olivia]

Thanks so much, guys. This is awesome.

[Randall Shepherd]

Take care.

[Olivia]

All righty.

[Randall Shepherd]

Bye.

[Olivia]

Bye.

[Monica Lilly]

That ran the gambit, didn't it?

[Randall Shepherd]

It certainly did. Almost every kind of story was within proposal. You don't know what you're going to get.

[Monica Lilly]

Don't know.

[Randall Shepherd]

It makes me think you could throw out any prompt, like, tell us a story about Tupperware. Tupperware. And then it would be like a skydiving disaster story.

[Jessica]

That's true.

[Monica Lilly]

You just don't know. Do you want to tell your proposal story before we go? I bet people would want to hear that.

[Randall Shepherd]

Okay. Similar to all these stories, it's funny how us guys we go get a ring and then we're going to try to plan some time so you have this thing for a while. And I had the great luxury of having Nicole in my life. So I took Nicole to the ring store and I said, I want to say first which one, but I want to then know what one you think she'll like like. And she said, there's two I think she would love. And I said, okay, great, don't say. And then I said, I like that one. And she got really excited and she said, that was my favorite of the two.

[Monica Lilly]

Oh, great.

[Randall Shepherd]

So that was lovely. I get the ring. I've told the story. I was about to give my credit card. What is this weird feeling I have? Very familiar feeling. It's a weird feeling. Specific, Specific. Oh, it's the moment you tell the tattoo artist after you look at the transfer, yes, I'll take it. And you go, okay, this is for life. So cut to. It's in my pocket of one of my jackets in my closet. And my plan was to go to this restaurant we had gone to early on. The first place. I said, I love you, which was Stanley's. It was her restaurant. And so I was going to say, let's go to Stanley's, which would have already been suspicious, but maybe it'll been a gesture. So that was going to happen. I guess I had thought sometime in January and it was Christmas Eve and my mom had flown in and we had both just got back from Michigan and we had this really, really wonderful Christmas Eve Eve. And then we were laying in bed and I thought, oh, I'm gonna try to recreate all this lovely feeling I'm having right now at this restaurant in three weeks, instead of just taking this moment that I feel like it should be. I was naked, I walked to the closet. I got the ring out of my jacket. She's like, why is he going to the closet? Then I came back to the bed and I kneeled down on one knee making. And then she started hysterically crying. And I asked and she said, yes, but she had cried so loud and long that the next morning getting coffee, when I saw my mom in the kitchen, she said, oh, sweetie, what happened? Did you guys have a terrible fight? I heard Kristen crying last night. I was like, oh, it was Christmas morning. She thinks we got into a real dust up last night.

[Monica Lilly]

That's funny. That's very sweet.

[Randall Shepherd]

Rob, did you have a ring for a while?

[Unknown]

Yeah, it was my grandma's ring. Ring that I got. The diamond reset. I made a Website for a fake restaurant that was like a prefix pop up.

[Randall Shepherd]

Okay.

[Unknown]

This is very wob and it was this Airbnb I rented on the lake in Chicago and it had this whole outdoor balcony and I had a friend that was a chef came and cooked a like eight course meal.

[Randall Shepherd]

Oh my lord.

[Unknown]

So we got to the Airbnb and he was there cooking and so did you pick any?

[Olivia]

Okay.

[Unknown]

No, it was by end of dinner. But we got there and it was just for us and she saw him there.

[Monica Lilly]

Lovely.

[Randall Shepherd]

Started putting together the pieces. Yeah, she's a bright gal. All right. Love you guys.

[Monica Lilly]

Love you.

[Unknown]

Do you want to sing a tune or something when it a theme song?

[Randall Shepherd]

Oh, okay, great. We don't have a them song for this new show, so here I go, go, go. We're going to add some random, random questions and with the help of armchairs, we'll get some suggestions on the fly rhyme dish on the fire rhyme dish.

[Cole]

Enjoy.

[Randall Shepherd]

Follow Armchair Expert on the Wondry app, Amazon Music or wherever you get your podcasts. You can listen to every episode of Armchair Expert early and ad free right now by joining Wondry plus in the Wondry Wondry app or on Apple podcasts. Before you go, tell us about yourself by completing a short [e-mail] survey.

[H]

Hey, everyone, it's your girl, Keke Palmer. Did you know I host a podcast called Baby this is Keke Palmer and you're not going to believe the conversations I've had. Like, is onlyfans only bad? How has dating changed in the digital age? What's the deal with Disney adults? I've talked to John Stamos, the vp, Kamala Hearst, to Jordan Peele, Raven Simone, and you. Yes, the one and only Jameela Jamil. And just wait until you hear our conversation. We talk Twitter drama, bad dates and then time. How the hell do you actually get sexy? Like, what the hell does that mean? Like, I know how to be funny. I know how to be like.

[Randall Shepherd]

You know what I'm saying?

[Jessica]

Exactly.

[H]

Like, I don't really know how to be like and take your clothes. I'm not robbing fucking givens. You know, it's like, how do people do that?

[Jessica]

I've been in this situation too many times and not not felt any of those things. The girl eyes, the quiet. Like I've never been quiet a moment in my life.

[H]

Yes, on Baby this is Keke Palmer. No topic is off limits. Follow Baby this is Keke Palmer on the Wondery app or wherever you get your podcast. You can listen early and ad free right now by joining Wondery Plus.