Desolate Dating

Haylie Shipp

Desolate Dating is a storytelling podcast about relationships in rural America, where the dating pool is limited and your social circles rarely reset. Hosted by radio personality Haylie Shipp. Launching Fall 2026. www.TinyURL.com/DesolateDating

Episodes

  1. 5d ago

    Seven Minutes in Miles City

    What do you do when you’re single, living in a small town, and wondering where exactly all these supposedly eligible people are hiding? If you’re Katie Rae Allison, you create your own speed dating event. Katie joins me from Miles City, Montana, to talk about what happened when she and a friend decided to give local singles another way to meet in the wild. We get into seven-minute dates, no-shows, age ranges, the courage it takes to keep showing up and why meeting someone face-to-face can tell you things a dating profile never will. We also talk about Katie’s own meet-cute, why sometimes you have to make the cool stuff you want to see in your community, and the very simple reality of rural dating: luck helps, but you still have to leave the house. And Katie is still creating cool stuff in Miles City. This fall, she and two other western makers are hosting Makers of the West, October 9–11, with makers, hands-on classes, shopping and a dance. Learn more about Makers of the West: https://www.makersofthewest.com/ © 2026 Ranchy Media LLC. All rights reserved. Desolate Dating is created, owned, and hosted by Haylie Shipp and produced by Ranchy Media LLC. Desolate Dating explores topics including loneliness, relationships, and emotional well-being. While we hope these conversations help listeners feel seen and connected, this podcast is not a substitute for professional mental health care. If you are struggling, please consider reaching out to a trusted friend, family member, your healthcare provider, or a licensed mental health professional. If you or someone you know is experiencing a mental health crisis or having thoughts of suicide, call or text 988 to reach the Suicide & Crisis Lifeline if you are in the United States or Canada. If you are outside the United States or Canada, please contact your country's local crisis services or emergency resources. If someone is in immediate danger, call 911 or your local emergency services. To sign up for the newsletter, give topic suggestions, or submit your own Desolate Dating story, head to www.tinyurl.com/DesolateDating.

  2. Aug 18

    Loud Chewers in Moose Jaw

    Grab a stool and pour yourself a drink. It’s time for Desolate Dating: After Hours. This time, we’re heading north of the border to Eyebrow, Saskatchewan, for a very unscientific look at rural dating with musician, farmhand and rural bachelor Jolie Blue. We’re talking six-hour round trips for dates, trying to squeeze in a love life before harvest, and what your married friends may not understand about being single in a small town. Then we get into the important stuff: bad excuses, listener-submitted icks, loud chewers, ratchet straps, questionable bathroom behavior and just how much you’re willing to overlook when your date lives relatively close. It’s loose, it’s slightly inappropriate, and it’s exactly what After Hours is supposed to be. Find Jolie Blue Jolie is a Saskatchewan musician performing as The Canadian Drifter. Find his music, social media and more at TheCanadianDrifter.ca. A quick heads-up: This episode contains a small amount of explicit language. The audio also gets a little rural in places thanks to internet quality. Jolie has promised to up his game next time. Like so many things with Jolie Blue, you accommodate for a star. © 2026 Ranchy Media LLC. All rights reserved. Desolate Dating is created, owned, and hosted by Haylie Shipp and produced by Ranchy Media LLC. Desolate Dating explores topics including loneliness, relationships, and emotional well-being. While we hope these conversations help listeners feel seen and connected, this podcast is not a substitute for professional mental health care. If you are struggling, please consider reaching out to a trusted friend, family member, your healthcare provider, or a licensed mental health professional. If you or someone you know is experiencing a mental health crisis or having thoughts of suicide, call or text 988 to reach the Suicide & Crisis Lifeline if you are in the United States or Canada. If you are outside the United States or Canada, please contact your country's local crisis services or emergency resources. If someone is in immediate danger, call 911 or your local emergency services. To sign up for the newsletter, give topic suggestions, or submit your own Desolate Dating story, head to www.tinyurl.com/DesolateDating.

  3. Aug 18

    Can't Keep a Caveman Down

    Why do we keep looking for love, even when we have full, happy lives on our own? In this episode of Desolate Dating, Haylie sits down with Joanne Hynes, a licensed clinical social worker in Glendive, Montana, to talk about why the need for connection is so deeply wired into us and what happens when you add the realities of rural dating to the mix. They talk about the very small dating pool in rural communities, the complete lack of anonymity when everybody knows everybody, dating after heartbreak, situationships, old relationship baggage and that nagging question: Am I actually ready to date again? Joanne also shares why you don’t have to perfectly “love yourself” before you can have a healthy relationship. Instead, she encourages self-awareness: know your patterns, understand your boundaries, be intentional about what you’re looking for and look for a relationship that adds to your life rather than trying to fix it. And yes, they also discuss caveman instincts, breakfast beer and the questionable mathematics of trying to calculate your actual small-town dating pool. Connect with Joanne Joanne Hynes, LCSW Email: joannehyneslcsw@gmail.com Joanne has also offered to help point people toward mental health resources, including options for those living in rural areas who may need to explore telehealth or other providers. A Quick Note Joanne is a licensed clinical social worker, but this conversation is meant to inform and encourage. It isn’t therapy, doesn’t establish a therapist-client relationship, and shouldn’t replace care from a qualified mental health professional. Thanks for pulling up a stool. We’ll see you next time on Desolate Dating. © 2026 Ranchy Media LLC. All rights reserved. Desolate Dating is created, owned, and hosted by Haylie Shipp and produced by Ranchy Media LLC. Desolate Dating explores topics including loneliness, relationships, and emotional well-being. While we hope these conversations help listeners feel seen and connected, this podcast is not a substitute for professional mental health care. If you are struggling, please consider reaching out to a trusted friend, family member, your healthcare provider, or a licensed mental health professional. If you or someone you know is experiencing a mental health crisis or having thoughts of suicide, call or text 988 to reach the Suicide & Crisis Lifeline if you are in the United States or Canada. If you are outside the United States or Canada, please contact your country's local crisis services or emergency resources. If someone is in immediate danger, call 911 or your local emergency services. To sign up for the newsletter, give topic suggestions, or submit your own Desolate Dating story, head to www.tinyurl.com/DesolateDating.

  4. Aug 18

    Tinder, Timing, and T. Rex

    What are the odds of finding the love of your life in one of the most remote places in America? For our first episode of Desolate Dating, we’re heading to Jordan, Montana, where the dating pool is small, the distances are big, and Kyle and JoAnna Fitch somehow found their way back to each other. Their story started on Tinder, fizzled out, and then got a second chance years later with a well-timed slide into the DMs. We talk about dating when your nearest options may be hours away, making long distance work, deciding who moves when two lives collide, and why finding your person may have less to do with checking boxes and more to do with finding someone you genuinely enjoy doing life with. We also get into ranch life, dinosaurs, a vegan moving to a cattle ranch, pregnancy three hours from the hospital, trash TV, cows with personality, and why sometimes you have to actually step into someone else’s world before deciding whether you belong there. Find Kyle & JoAnna Follow Kyle Fitch Findings on Instagram to see what Kyle and JoAnna are uncovering on the family ranch, including fossils from Montana’s Hell Creek Formation: Kyle Fitch Findings on Instagram Kyle and JoAnna also sell some of their fossil finds through DinoJo / Kyle Fitch Findings LLC on Whatnot. They’re currently taking a break from live shows, but you can follow their page for when they get going again. DinoJo on Whatnot What Are Cattle Earmarks? When JoAnna talks about her first branding experience, the conversation turns to cattle earmarks. For listeners who didn't grow up around livestock, earmarks are permanent identification marks made by cutting specific patterns into an animal’s ears. They can complement a livestock brand and can also be useful for identification and herd management. Want to see what terms like a crop, split, under bit or swallow fork actually look like? How to Read Cattle Earmarks: A Visual Guide Join the Desolate Dating Conversation Desolate Dating is about what it really means to look for love and connection when you live somewhere the dating pool is more of a puddle. We’ll share rural success stories like Kyle and JoAnna’s, but we’ll also talk with singles and specialists, hear from listeners, explore loneliness and isolation, laugh about the absurd parts of dating, and have honest conversations about what happens when finding your person really is a numbers game. Visit TinyURL.com/DesolateDating to submit your story or topic ideas, sign up for the Population: Single newsletter, and find links to our social media pages. © 2026 Ranchy Media LLC. All rights reserved. Desolate Dating is created, owned, and hosted by Haylie Shipp and produced by Ranchy Media LLC. Desolate Dating explores topics including loneliness, relationships, and emotional well-being. While we hope these conversations help listeners feel seen and connected, this podcast is not a substitute for professional mental health care. If you are struggling, please consider reaching out to a trusted friend, family member, your healthcare provider, or a licensed mental health professional. If you or someone you know is experiencing a mental health crisis or having thoughts of suicide, call or text 988 to reach the Suicide & Crisis Lifeline if you are in the United States or Canada. If you are outside the United States or Canada, please contact your country's local crisis services or emergency resources. If someone is in immediate danger, call 911 or your local emergency services. To sign up for the newsletter, give topic suggestions, or submit your own Desolate Dating story, head to www.tinyurl.com/DesolateDating.

  5. Aug 6

    Welcome to Desolate Dating | Official Trailer

    Finding someone to build a life with is complicated. People are going to tell you it's about timing. You just need to put yourself out there. Or my personal favorite: it always happens when you quit looking. But let's face it. When you live in small-town America, sometimes the biggest challenge is much simpler... there just aren't that many people to meet. Hi, I am Haylie Shipp. I am a rancher in Montana. I'm a farm broadcaster who's spent the last 20 years telling the stories of rural America. But throughout all of those years, I realized there was one story we weren't telling. And it's the one I'm living: what it's really like to navigate dating and relationships when you live in a place where there simply aren't that many people to meet. This is Desolate Dating. Every week, we're going to hear from people who found love against the odds, people who are still searching, and people who have built fulfilling lives after making peace with being on their own. We'll talk with experts. We'll laugh through some truly unbelievable dating stories and have some honest conversations about loneliness, hope, resilience, and the realities of trying to build a life when your opportunities to meet someone are few and far between. Most of all, I hope this podcast reminds you of one thing: you are not alone. If you've ever driven hours for a first date or opened a dating app only to recognize every single profile, you're not the only one. Thousands of people across rural America are navigating these very same challenges. If any of this resonates for you, the first three episodes arrive on August 18. I would love for you to follow or subscribe today. Recommend this to a friend. It's one of the biggest ways you can support a brand-new podcast, and it means those first three episodes will be waiting for you the moment they're released. Then, head to www.tinyurl.com/DesolateDating to become part of the community. You can sign up for our newsletter, follow the social media pages, share your own story, and stay connected between episodes. This podcast is not just about dating. It's about finding community. It's about sharing a few laughs in what is a really hard and isolating experience. And it's about having honest conversations. Thank you for being here from the very beginning. I'll see you on August 18. © 2026 Ranchy Media LLC. All rights reserved. Desolate Dating is created, owned, and hosted by Haylie Shipp and produced by Ranchy Media LLC. Desolate Dating explores topics including loneliness, relationships, and emotional well-being. While we hope these conversations help listeners feel seen and connected, this podcast is not a substitute for professional mental health care. If you are struggling, please consider reaching out to a trusted friend, family member, your healthcare provider, or a licensed mental health professional. If you or someone you know is experiencing a mental health crisis or having thoughts of suicide, call or text 988 to reach the Suicide & Crisis Lifeline if you are in the United States or Canada. If you are outside the United States or Canada, please contact your country's local crisis services or emergency resources. If someone is in immediate danger, call 911 or your local emergency services. To sign up for the newsletter, give topic suggestions, or submit your own Desolate Dating story, head to www.tinyurl.com/DesolateDating.

Ratings & Reviews

5
out of 5
33 Ratings

About

Desolate Dating is a storytelling podcast about relationships in rural America, where the dating pool is limited and your social circles rarely reset. Hosted by radio personality Haylie Shipp. Launching Fall 2026. www.TinyURL.com/DesolateDating