Armchair Anonymous: Bad Proposals

0:00Welcome, welcome, welcome to Armchair Anonymous. I'm Randall Shepard. I'm joined by Monica Lilly. Oh, that was cool. It was hard. Okay. The prompt was bad proposals. Proposals gone wrong. Yes. But oh my Lord. I mean, this is like tied with that crazy bear attack or shark attack. This goes some places. It really builds this one. It just gets more and more intense. Yeah. And then the last one is a nail biter. Wow. Wow. This is a banger. Yeah. Please listen to this one. And happy Valentine's Day. Oh, is that what it is? Yeah, it was meant to pair up a little bit. Okay, great. Yeah, happy Valentine's Day.

0:39May your heart be full of love and merriment. And in his name we pray. He has risen. What are you going to do for Valentine's Day? Eat chocolates? I'll try not to. Yeah. I mostly think of my mom always would ask me to be her Valentine. Oh, that's sweet. Yeah, and so I'll ask the girls to be my Valentine. That's cute. in there they'll still like it they'll oblige yeah did your dad ever ask you to be his of course not yeah did you guys do Valentine's Day we didn't even have it yeah well we did my mom no my mom would sometimes bring these would she get you a box of chocolate yeah my mom would get us a box of chocolates I think she would do something nice every now and then but I'm not gonna get my kids anything because they're already spoiled they already have too much chocolate why don't you tell them that on Valentine's Day be my Valentine's Day I'm not getting you anything you're gonna repent this Valentine's Day Please enjoy Bad Proposals.

1:52Cole? How you guys doing? Good. Can you hear us? Yeah, I can hear you guys. Can you hear me? Yes. Where are you, Cole? All right. I was really worried about the sound quality, so hopefully it's all right. I am in my closet here. 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. I'm through four doors. I can go in a different room here. Now we're getting a nice tour of your home. I can go to the home office here. Somehow got worse. I hate to say this. So I was right. We've lost the visual of you. Can I ask one last thing?

2:27Would you be willing to go to that first room you walked into? Because it was dynamite in there. My wife is getting ready for work here. Oh, sorry. Our apologies. Sorry. Now we've got great image. We've got great sound. Hi. Tell her we say hi. She's stressed. She says hello. All right. Now we're talking. Cole, where are you? I'm in Billings, Montana. Oh, that explains the spotty Wi-Fi. Yep. This story may or may not involve some other spotty cell service areas. Okay, great. Are you from Billings? No. So I'm originally from Stroudsburg, Pennsylvania. What brought you to Montana? Work. You're a strong man.

3:07You've got broad shoulders. Are you doing something physical? I am not. I'm actually a chemical engineer, but I do work at a refinery. Are you lifting incredibly heavy test tubes all day? That's right. I load them up with the lead and all the other heavy things. Okay, great. Cole, hit us with this bad proposal. The bulk of it is in Billings, Montana. I've lived here for about four years now. I was proposing to 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.

3:46So 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 a gorgeous proposal. Get engaged. I love it. 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 at 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.

4:24Jesus. 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. I'll tell you what. It made it there no problem. Oh, that was a red herring. But now, fast forward to October, November, we've kind of 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 we're 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.

5:00So 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. Right, right. 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 and ship the ring back through the mail. I can't send it to my house because she might open it.

5:36So I got to send it to a friend's house now. So I'm not even receiving this thing. Again, the ring gets here unscathed. Oh, USPS, whatever it is. Good job. 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. Are you guys happy for me or what? And the next thing I see pop up is Tess was removed from the group chat.

6:15Oh no. She was on it? Oh Jesus. 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, fuck. 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.

7:00Get your shit sorted out. Oh, good boss. That is a good boss, but he was upset. Yep. So I got about four hours until she gets home from work. I'm doing the whole nine. 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. Oh, boy. Quick troubleshooting. Find the first number for a remote Apple support. Call it. And they're just like, you know what? We can fix this problem. them. It's going to cost about$250. If you download the screen sharing app, we can really see what's going on here.

7:36So I download the screen 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. 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. I hang up on the guy, immediately 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, liar, hang up again. Now I'm smarter than you. Some lies do it. So thankfully I avoid getting scammed. At any point, do you think the Lord is telling you to not get married to this woman?

8:16If that's what he was trying to say, I powered through. Oh God, good, good. Finally, she gets home. I proposed 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 cell service. We're about a half mile from the trail head. I can see the trail head 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?

8:52All 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 squeaked through the second snow drift. And then I see a third one coming up. And I think to myself, you know what? It worked less. 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. Cole, do you recognize you're an interesting mix of brilliant as hell and dumb as fuck? 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.

9:32That works more of a PG version, but yeah. 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 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. Oh, that's not going to help. I tell my fiance and 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. This is miserable. Do you think she was like, I don't want to go through with this?

10:13She must be thinking there's a lot of red flags. I'm worried 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, yo. Oh, boy. Oh, wow. Oh, yeah. That's a rough start. But can only go up from there. That's a good silver lining. We got married on December 29th just celebrated our first year of marriage.

10:54Congratulations. You went through hell and high water or high snow to get there. Call your delight. This gal, as shitty as the proposal was, is a lucky woman. And we got to meet her. We didn't even re-along. I did not tell her that I was going to try and commandeer the closet. And she comes in at like 140 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. High stress feels like it might be status quo. These are not really abnormal situations for me, unfortunately. Oh, this is great. It's a delight meeting you.

11:26Thank you for telling us that story. We're so sorry you went through all that. 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, you got it. Oh, well, thank them for us. All right. Great meeting you. Nice to meet you guys. Thanks. Hi. Is this Olivia? Yeah. Look at your sweater. Just for you guys and my earrings. Cherry to the max. For a second, I thought they were tattoos. When I just first glanced, I thought those were your arms. No cherry tattoos yet.

12:02I have an orange and a peach. Oh, so that would go perfectly into your fruit aesthetic. It would. You're in a legit sound booth. 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! Get out of there. I don't care what audition you have. Are you in California? No, I'm in Syracuse, New York. Oh, okay. He's doing voice work up there. That's interesting. Remotely. Nice. Okay, so you have a bad proposal story. Since you guys started doing Anonymous, I was waiting for this prompt. I said, when this prompt comes out, I am locked in.

12:37They're going to pick it. And everybody in my life is 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. That's right. This is our proposal. May 15th, he says, we're going to go out to dinner, wear a nice dress.

13:12I'm going to pick you up. And I'm like, okay, it's going to 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. What the fuck? This is where he and I had our first date. Can you tell us what the trail of terror is? 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.

13:51And 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. It's like a haunted trail. Year round? 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 makeshifted 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 day. This is where it's going to happen.

14:23But I am oldest daughter, Virgo, notorious rule follower. Don't like to take risks. I'm 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?

14:59Oh no. 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 trespassing and i'm like i knew this was going to 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 am like this is how i'm about to die and my parents are going to find out that i trespassed and i went to trail and that's how I was murdered by this man with a shotgun. He wants to make an example out of you two.

15:51The 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. Are you kidding me? 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. This is a horror movie. I'm kind of laughing because I'm so nervous. Like I'm having fight or flight, but freeze, I guess. Yeah. I look at Paul. He doesn't look nervous about them. He's like afraid of me in the moment.

16:27It all clicks. He did not. Did you do this? Oh, I wasn't there. He planned it. He was totally in there. Oh my God. That's spectacular. He kneels down and pulls the ring out. We're still surrounded. Oh, pictures. It's so scary. 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 fucking masks. No, these are Atelier bespoke masks. Your husband has the most nervous laugh smile on his face looking at you. So he reached out to the Trail of Terror and said, hey, this is where we had our first date.

17:21I know it's your off season. And 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 going to pop out somewhere. Like the gun was not mentioned. Threatening of our lives was not mentioned. 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 to walk into the car.

17:56It was so pissed. I was like, I'm taking my ring. I'm getting the fuck out of here. Yeah. No party. You liked it, right? 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. Wow. Do you start thawing as you see it's your own friends? Yeah. And they brought a bottle of champagne. And she had it ready. And then I started to relax. That is so funny. It was really scary. Yeah.

18:28What does that group of folks do between October and the following October? It's so funny because the guy who sent the whole plot that works at the trail, he's like, I'm going to see if I can round up some guys. Larry's got volleyball tonight or whatever. They're just normal dudes. But he's like, my scarers are around. They're just jonesing to scare some people. Yeah. And is your life fun like this? He is so fun. Oh, I love this. We have two little kids now, and I still pick on him for this. And he's like, it's so special. But I was traumatized for a bit, but I wouldn't trade it. Obviously, I got to talk to you guys.

19:03That's one step away from choreographing a car accident. You get T-boned, and then the ambulance comes in. It's your mom and dad, and they've got you. Look, it's memorable. For sure. 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 it's so loud and clear. At the end, I say, white guys with guns are my biggest fear.

19:29If he 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. Really ups the stakes in a hurry. You were right to know this would get picked. Yeah. I don't think we're going to have a story like this. I really had a feeling. I'm so glad. He is here. And also my siblings are here. if they could just peek their heads into the sun booth. Hi there. This is the husband. You have the most adorable, nervous smile in all those photos. Like, is she going to get over this? Oh my gosh. I was worried. What a swing you took. I know. I didn't intend to do anything scary, but he was just so passionate about it and so excited.

20:07And he was like, I'll get my crew. That's a nice thing you did for them. Yeah. It made it fun. We love you guys so much. Oh, hi. You guys are so cute. It's delightful to meet you guys. So nice to meet you all. We're so happy Liv got to tell her story. It was hysterical. Yes, unbelievable. I was completely on the hook. Did not see it coming. Monica got it. She was a little ahead of me. A little ahead. It took a while, though. It was great. It was so lovely to meet you guys. Yes, you guys do. Take care. I went into a hole. I totally believe these crazies live in that barn waiting. I could have gone that way.

20:44How would I? You would. well you don't know I don't know you're right but when you get scared I mean I would be crying right yeah so then I maybe I would be crying but I would also be happy that would be nice that would be nice which would you rather happen the proposal on the Jumbotron from last week or this I would rather this yeah you wouldn't be hated then you're surrounded by love family and friends and champagne all the stuff they wanted just to get through this other part first I mean I guess Then you're really hopped up. Your adrenaline is up. Aroused. You're aroused. Hop in the back of the car.

21:20Maybe that's a fun evening. You're feeling like life is so short. You get the chainsaws going in the background. Oh, hi. Hi. Jessica, where are you? I'm in Texas. Ooh, la la. Where? What part? Fort where? Did you grow up there? Yes, but I, at 18, flew out of here like a bat out of hell into Colorado. Oh. Okay. 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.

22:00So 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 to go up. I'm complaining about this. I'm like, I don't want to do it. I I understand why I have to do this. Yeah, we just go up there on your own and get the fucking shot and then come home. Well, apparently he has to go with somebody because it's dangerous. I'm just himming 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. No, you just have a boundary.

22:32I 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. Oh, geez. 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.

23:07At any point, are you getting the least bit suspicious? 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. This is not my dream proposal situation. No. 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. 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.

23:43I just need one thing for 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. Oh, wonderful. You're at the top of a mountain of a really difficult height. 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. Oh, no. Yeah, this is tough. 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 impending, the moment that is supposed to be so special.

24:31You'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 fucking four-hour hike in the middle of the night on this mountain you did say no oh that's the funny thing i look back now and i never said yes, but it wasn't assumed yes. Right. Not now means like later.

25:07I'm just crying. And we get down the mountain and he had 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. Probably picked the wrong girl for that whole exercise. Because no, she said so many times. No, no, 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. Okay. I got to panic. You hold up your hand. I'm like, oh fuck, you're happily married.