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
Montana State Auditor and Commissioner of Securities and Insurance James Brown joins host Haylie to expose romance scams and AI-driven fraud, offering crucial warning signs to prevent financial heartbreak.
6 Oct 2026
Delulu on the Prairie
Host [Host Name] explores dating standards and unrealistic expectations with listeners, particularly those navigating rural dating pools, in this interview episode.
29 Sept 2026TRANSCRIPT
Cinderella Flees the Shanty
Greg and Alysia Mosness share their unexpected journey to finding love in rural Montana, revealing how connection blossoms even in a small, familiar dating pool.
22 Sept 2026
Maggots, Missing Groceries, and Accidental Incest
Host Haylie shares a shocking story about maggots on a date, highlighting the bizarre nature of dating experiences.
15 Sept 2026TRANSCRIPT
Rejection and Other Small-Town Spectator Sports
Mental health therapist Kathleen Raml joins host Haylie to explore navigating romantic rejection and its amplified impact in small-town dating.
8 Sept 2026TRANSCRIPT
You Should Probably Know This About Me
Host [Host Name] shares the personal journey and motivations behind the "Desolate Dating" podcast, exploring rural relationships and connection.
1 Sept 2026TRANSCRIPT
Wear the Damn Ring w. The Farm Babe
Host [Host Name] interviews agricultural advocate Michelle Miller, "The Farm Babe," about navigating rural dating, apps, and long-distance relationships while building a national career.
25 Aug 2026TRANSCRIPT
Seven Minutes in Miles City
Host [Host Name] interviews Katie Rae Allison about her experience creating a unique speed dating event in a small Montana town, revealing insights into local dating challenges and the courage to connect.
18 Aug 2026TRANSCRIPT
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-su...
18 Aug 2026TRANSCRIPT
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 heartb...
18 Aug 2026TRANSCRIPT
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...
6 Aug 2026
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 Americ...
Inside a recent episode
Your Soulmate Needs a Wire Transfer
Published 13 Oct 2026 · Transcript excerpt
[…] So, What do people, what should they do if they suspect a scam? First of all, the number one reason that Montanans who have been scammed tell us that they didn't report the scam or that they had lost money was because of the fear of embarrassment and they felt stupid. The reality is these scammers literally have made scamming their business. To get to the thrust of your question, the first thing we encourage people to do is to actually just report the scam. We are at the state auditor's office, the repository for reporting financial type scams in Montana. But the thing that we also tell folks is if you think you're being scammed, just like we heard as a kid, you know, if you're on fire, stop, drop and roll, right? […]
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