Even a bad date gives you a good story.

After a couple of heavier episodes, we’re lightening things up with three dating stories that could probably only happen in Desolate Dating territory.

First, Haylie has a date over to her house when she notices a few innocent-looking “caterpillars” in the kitchen. Spoiler: they were not caterpillars. They were maggots. Falling. From. The. Ceiling.

Then, two listener voice memos prove exactly why we need more of you to send these things in.

One takes us back to the early days of Match.com, when a rancher welcomed a date into his home during calving season... only to discover after she left that nearly all of his groceries had disappeared.

And finally: the family photo album you absolutely do not want to recognize yourself in. A college relationship, a weekend meeting the parents, cucumbers being washed in a bathtub, and the sudden realization that her cousins were also his cousins.

Through marriage. No blood relation. We need to make that VERY clear.

HAVE A STORY? WE WANT IT.

The listener voice memos are pure gold, and we want more of them.

Dating disasters. Success stories. How you met your spouse. Something weird, hilarious, heartbreaking or so unbelievably small-town that nobody outside your zip code would understand it.

Record a voice memo or send your story at tinyurl.com/desolatedating.

Voice memos can be up to five minutes long. Once submitted, your story becomes the property of Desolate Dating and Ranchy Media LLC and may be used on the podcast, in print or on social media. Want to stay anonymous? Just say so.

THANKS TO OUR PRESENTING PARTNERS

The Moss Lodge by Arneson Contracting
A whimsical stay on the Milk River in Glasgow, MT, with acreage to roam, a treehouse overlooking the river, hot tub, and main house built for entertaining.

Glasgow Dental Clinic
Dr. Jolynn Capdeville and the team at Glasgow Dental Clinic are keeping northeast Montana smiling and supporting real conversations about dating in rural spaces. Call (406) 228-2656.

AND OUR FOUNDING SPONSORS

A huge thank you to the businesses supporting Desolate Dating from the beginning:

Ooo Shiny Fabrics

Cherry Creek Aesthetics

Busted Knuckle Brewery

End of the Road Vacation Rentals

Dr. Kristen Strom — Keynote Speaker and Coach

JWhittle Construction LLC — Nashua, MT

Interested in becoming a Founding Sponsor? The window is open through October 31, 2026. Email [email protected] for details.

FIND DESOLATE DATING

Listen. Watch. Subscribe. Send us your stories.

tinyurl.com/desolatedating

And if you enjoyed this episode, send it to the friend whose dating story NEEDS to be on this podcast.

© 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.

Rejection sucks. There’s really no sophisticated way to say it.

And when you’re dating in a small town or rural space, getting rejected can feel even more personal because sometimes it feels like you have an audience. Who knows? Who’s talking? What are they saying? And why does it suddenly feel like everyone has an opinion about your dating life?

In this episode of Desolate Dating, Haylie sits down with mental health therapist and substance abuse counselor Kathleen Raml to talk about romantic rejection, self-worth, and the stories we tell ourselves when something doesn’t work out.

They get into why rejection can hurt even when you weren’t all that interested in the person doing the rejecting, how changing “they rejected me” to “we weren’t a match” can shift the way we experience it, and how to deal with the very real, or sometimes perceived, small-town audience watching it all unfold.

They also tackle falling in love with the potential of a relationship before there actually is one, keeping one foot planted in reality while still letting yourself be a romantic, and knowing when it might be time to talk to someone.

Plus: Haylie learns it is perfectly acceptable to reject your therapist, and Kathleen shares the very unscientific beginning of the relationship that turned into her 20-year marriage.

Connect with Kathleen

Therapy: Kathleen provides mental health services through Integrated Therapy Solutions in South Dakota and Minnesota. Learn more about her services at Integrated Therapy Solutions or follow Kathleen’s therapy page on Facebook.

Katie J Entertainment: When she’s not working as a therapist, Kathleen also performs as Katie J, offering DJ services, karaoke and live music. Find her and booking information on Katie J Entertainment on Facebook.

Thanks to Our Sponsors

A huge thank you to the businesses supporting Desolate Dating and helping make these conversations possible.

***Presenting Partners***

The Moss Lodge by Arneson Contracting
Stay at The Moss Lodge on Airbnb
Arneson Contracting & Construction

Glasgow Dental Clinic

***Founding Sponsors***

Ooo Shiny Fabrics
Ooo Shiny Fabrics

Cherry Creek Aesthetics
Cherry Creek Aesthetics

Busted Knuckle Brewery
Busted Knuckle Brewery

End of the Road Vacation Rental
End of the Road Vacation Rental on Facebook

Dr. Kristen Strom at Rooted in Wellness
Rooted in Wellness

J. Whittle Construction

A Note About Mental Health

This podcast is intended for conversation, education and entertainment and is not therapy or a substitute for professional mental health care. If you are struggling, please consider reaching out to a qualified mental health professional or appropriate support resource in your area.

About Desolate Dating

Desolate Dating is about the reality of looking for connection when the dating pool is small, the distances are big, and everybody seems to know everybody.

Subscribe, follow, rate, review and share the show with somebody else navigating love, loneliness and dating in rural spaces.

© 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.

The highly redacted story of how I got here and why Desolate Dating exists.

This episode of Desolate Dating is different.

No guest. No interview. Just me, sharing a little of the story behind this podcast and why conversations about rural dating, loneliness, relationships and connection have become so important to me.

Consider this the Cliff’s Notes version of my diary. Not a tell-all. Definitely not a full dating history. But enough to understand the person behind the microphone and why I wanted to create a podcast about what it’s really like to be single in rural America.

I talk briefly about losing my brother, Dusty, to suicide in 2021 and how his experience with loneliness became an incredibly personal part of my “why.” At its core, Desolate Dating exists because I want people to feel less alone in their loneliness.

I also share my decision at 37 to stop waiting for the right relationship to create the family I knew I wanted and become a solo mom by choice.

Then there’s the highly redacted dating history. Four significant relationships. One engagement. Some lessons about what I want, some lessons about how I want to be treated, and the uncomfortable acknowledgment that sometimes I haven't been particularly great at relationships either.

And then there’s my current reality: 41, very single, raising a little boy, living 20 miles outside a Montana town of roughly 2,700 people and absolutely NOT using this rural dating podcast to find myself a man.

Small-town dating comes with a particular kind of math. Limited dating pools. Long distances. Everybody knowing everybody. Friends, exes and histories that overlap. Sometimes the challenge isn't simply finding another single person. It's finding someone who actually fits into your life.

That's what we're here to talk about.

Desolate Dating is for people navigating dating and relationships in rural communities, small towns and geographically isolated places. It's for people who know the ache of loneliness. It's for the families and friends who may not understand why finding someone isn't quite as simple as “putting yourself out there.”

And yes, it's also for those of you who are happily partnered but simply cannot look away from the spectacle.

This isn't a podcast about bashing men, women, relationships or being single.

It's about connection. It's about telling the truth about dating when geography isn't exactly working in your favor. And hopefully, it's about helping people feel a little less alone in their loneliness.

Thanks for pulling up a stool.

MENTAL HEALTH NOTE

This episode includes a brief discussion of suicide, grief and loneliness.

If you or someone you know is struggling or in crisis in the United States, call or text 988 to reach the Suicide & Crisis Lifeline. You can also chat with the 988 Lifeline at 988lifeline.org.

If you are outside the United States, please contact your local emergency services or a crisis support service in your country.

THANK YOU TO OUR SPONSORS

A huge thank you to our Presenting Partners, Arneson Contracting and Glasgow Dental Clinic, for believing in Desolate Dating and helping make these conversations possible.

Arneson Contracting
https://www.arnesoncontractingconstruction.com/

Glasgow Dental Clinic

And thank you to our Founding Sponsors:

Ooo Shiny Fabrics
https://www.ooshinyfabricsllc.com/

Cherry Creek Aesthetics
https://www.cherrycreeka.com/

Busted Knuckle Brewery

End of the Road Vacation Rental
https://www.airbnb.com/rooms/865794729425954666

Dr. Kristen Strom at Rooted in Wellness
https://www.drkristenstrom.com/

DESOLATE DATING

Listen, watch, follow along, join the Population: Single newsletter or submit your own story:
https://tinyurl.com/DesolateDating

Interested in becoming a Desolate Dating sponsor? Founding Sponsorships are available through October 31, 2026.

[email protected]

© 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.

What happens when the Farm Babe talks less about farming and more about dating?

Michelle Miller, better known as the Farm Babe, joins Desolate Dating for a candid and funny conversation about rural dating, dating apps, long-distance relationships, and what it’s actually like to look for love when your career takes you all over the country.

Michelle is an agricultural advocate, keynote speaker, author, podcast host and social media personality who has built an audience of more than 400,000 followers. But in this episode, we’re skipping the agricultural myths and politics and talking about something arguably just as complicated: finding a good person to date.

We get into the Hollywood version of marrying a farmer or rancher, whether farm conferences are actually a good place to meet someone, meeting a rancher “in the wild,” dating-app fatigue, bad profiles, long-distance dating, and what actually makes someone stand out.

Michelle also shares what she’s looking for in a partner, why a little dirt isn’t necessarily a dealbreaker (hygiene, after all, is relative), and why married men at agricultural conferences need to wear the damn ring.

Underneath the laughs is a conversation a lot of single people will recognize: dating takes work. Geography matters. Timing matters. And being a successful, driven person doesn’t automatically make finding your person any easier.

CONNECT WITH MICHELLE MILLER | THE FARM BABE

Learn more about Michelle, her work, speaking and social media at:

The Farm Babe

THANK YOU TO OUR PRESENTING PARTNERS

Desolate Dating is proudly supported by our Presenting Partners:

Arneson Contracting & Construction

Glasgow Dental Clinic

THANK YOU TO OUR FOUNDING SPONSORS

Oo Shiny Fabrics

Cherry Creek Aesthetics

End of the Road Vacation Rental

Dr. Kristen Strom

BECOME A FOUNDING SPONSOR

Founding Sponsorships for Desolate Dating are available through October 31, 2026. If your business or organization would like to support honest conversations about dating, connection and life in rural communities, contact [email protected] for sponsorship information.

ABOUT DESOLATE DATING

Desolate Dating is a podcast about dating, relationships and connection when the population is small, the distance is big, and finding your person can feel like a numbers game. Through honest conversations, real stories and plenty of humor, we’re talking about what dating actually looks like in rural America.

© 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.

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.

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.

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: [email protected]

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.

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.

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.