Desolate Dating

Are your dating standards actually reasonable... or are you a little delulu?

This week on Desolate Dating, we're talking about dating standards, unrealistic expectations, and those lists we build when we're looking for a partner, especially when you're dating in rural America and the dating pool is already pretty dang small.

It all started with an anonymous male listener telling me about a VERY awkward Zoom date set up through a prof...

What does dating look like when you live in rural Montana, everybody knows everybody, and your dating pool feels incredibly small?

For Greg and Alysia Mosness, finding love in a small town happened when neither of them expected it. Alysia was navigating life after divorce, raising two kids and pretty convinced she wasn’t interested in dating at all. Greg had tried online dating, including Farmers Only, moved to small-town Mont...

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...

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 healt...

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 e...

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 me...

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 ...

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 i...

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 a...

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 abo...

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 sp...