4 Funny Pet Sitting Stories To Make You Smile And Help Understand What We Do

Humor is the best medicine and these funny pet sitting stories still bring a smile to my face as I read them today.

I mean, seriously, who can pass up laughing at our pets when they do silly things. Pet sitters like myself see plenty of strange things in the course of business, here are 4 funny stories from my pet sitting journey way back in 2013…

Funny Pet Sitting Stories

Locked In On Halloween Night

It’s Halloween. After a long day pet sitting in Muncie, I had one final visit to do in Hartford City then I could go home and curl up with my pets.

This routine 20 minute drive took an excruciating 45 minutes due to horrendous fog and freezing rain.

Upon my arrival, I heard a cacophony of dogs barking from one area in the house. The sound of 3 great danes barking is pretty amazing if you haven’t heard it before. Not only were they barking frantically, they were scratching on the door to get out. As I’m yelling, “It’s OK guys, hold on!” I kinda freak out because the door was locked, from the inside.

Everything I tried to ‘break in’ failed to work. The panic set in more. A slew of thoughts came racing in my mind, such as: “What was I going to do?”, “Did they destroy the bed and furniture?” and “Did they poop and pee all over the carpet?” I tried to find the humor in the moment but it was rather difficult under the circumstances.

Luckily, my McGyver skills worked, I got in and the room was unscathed for the most part. But if you look at the back of the door it looks like Edward Scissorhands came by for a visit!

But the story doesn’t stop there. The humor (and panic) continued…

Once I let all 9 dogs outside to pee, I worried. I worried because it was pitch black, foggy as hell and it was Halloween. Crazy stuff happens on that night. I didn’t need any other crazy things to happen on my watch.  You see, if I outstretched my arm in front of me, I couldn’t see my hand. A dog definitely couldn’t see danger if it was lurking in the fog. Not long after that, the wandering danes strolled in, one after another.

Anyway, as I called the dogs back home, no one came. I waited and waited. Paced, hollered and waited longer. After 30 minutes I got into my truck, drove it down the drive a little and began flashing the bright lights and honking like a mad woman. I even went so far as to get a frying pan and a wooden spoon and I proceeded to beat that thing like my life depended on it.

I showered them with kisses and hugs and then I checked them out from nose to tail to make sure they weren’t injured in their little adventure.

In this line of work you have to keep a sense of humor and be flexible. You just never know when you’ll have to honk your horn and knock on a frying pan so the dogs can find their way home!

Santa’s Helpers

Imagine this: It’s pitch black outside.

The ground is covered in ice. It’s cold and raining.

Visibility is down to a minimum and the drive way I’m going up is long and it’s on a steep incline.

Even with the 4-wheel drive in gear I’m slipping and sliding.

Once I get to the top of the hill I can barely see the 3 dogs. Due to a lack of outdoor light, all I had was my little headlamp that I strapped on so I could use both of my hands. Let’s just say few little LED lights doesn’t cut it when it’s that dark outside (and one reason we ask our clients to leave lights on for us).

So I get to the dogs in their yard. They were bouncing all over the place, clawing at me and jumping up which was pretty dangerous on that particular night. They were soaked and ready to get into the warmth after being outside all day with little comfort. Can’t say I blame them for acting like crazed animals. I probably would be too in that situation.

Normally I’d take all 3 dogs inside at once. However, I thought it would be safer to do it individually.

I’m really trying to not get frustrated at the clients for not having hiring someone salt and plow (and have lights on for me), so instead I muster some laughter. However, that quickly fades as I realize I’m going to have dogs in tow here in just a few minutes.

One dog lets me leash him up. We begin to across the  ice skating rink,  oops, driveway. As soon as his feet hit, dog and human legs start going every which way. I laugh, I cry, I bust my butt, get up, I laugh, I cry and I fall again.

The decline of the drive way didn’t help. Once the dog got his footing, he headed DOWN the driveway, not up, towards the house. While he’s trying to run down the hill, I go face down, on my belly. Laughter starts but then the tears fall. All I can think of is Santa, Rudolph, sled…flying through the air. My hands were froze yet I kept a death grip on the leash. Santa’s helper #1 succeeded in taking me on an icy adventure.

Santa’s helper #2 and #3 also had problems traversing the ice. Again, I went down, was pulled every which way and finally got control.

We made it into the house where they could warm up and eat. I drove home with a tear-streaked face, snotty nose, frozen hands, sore throat from yelling at the dogs to slow down and stop, scraped hands, torn pants, skinned chin and plenty of sore spots.

This right here is a good example as to why it’s important we have proper lighting to work in and ice free zones.

Rolling in the Hay

On a clear summer day, I went to a farm sitting job. I loved that job because they had donkeys, chickens, cows, dogs and farm kitties and best yet, everyone was friendly and liked human interaction!

One of the dogs, a hyper Border Collie, runs and jumps on me, gives me a lick and then takes off.

She ignores my calls and continues on her mission out in the pasture.

Following her outside, I see her rolling in the hay. But it’s not just hay. There’s a big cow patty smooshed all around. She rolls from side to side, making sure to get the poop all over. She looks at me with the funny grin on her face while her tongue flops around.

Luckily her mom and dad are used to this naughty behavior. Living on a farm you have to have a good sense of humor.

Raw Feeding is for The Birds

Nothing against raw feeding, I support it wholeheartedly if it’s done correctly. Raw feeding provides great nutrition and is a much healthier diet than most of the commercial dog foods on the market but…when part of the raw feeding diet consists of an intact bird, I have to draw the line.

The dog in my care was extremely healthy, loved and uber spoiled. His mom and dad had been feeding him raw for about two years and in that time, his routine ear infections subsided and the constant dry skin cleared up (two common side effects of healthy raw diets).

Normally the meal consisted of organ and bone but on this particular visit, a frozen bird was also in the bag.

The dog ate everything BUT the bird and looked up with a quizzical look on his face. Can’t say I blame him. I’d probably think someone was crazy too if they changed up my dinner like that.

When I texted his mom and dad and told them his reaction they laughed and said they weren’t sure if he’d eat it. So instead of them seeing if their dog liked tweety, they let ME be the bad guy.


Our team of pet care providers have tons of funny pet sitting stories to share; so much so, we could write a book! However, these are just 4 of the hundreds that came to mind first when this article was written. If you didn’t see the humor in these stories, believe me, I lived through them and can tell you for sure I laughed. Sometimes I laughed instead of crying, lol.

Pet sitting isn’t for the faint of heart or for people that get squeamish easily. Well…that’s not entirely true because the frozen bird made my belly turn…but you know what I mean.

We have to laugh at what happens in this profession. People would be surprised with some of the stuff pet sitters and dog walkers go through. Being a Grinch doesn’t help anyone and we just have to grin, go with the flow and come back to normalcy as quickly as possible and get the job done.

Finding the joy,

Kelley Stewart, CEO|Pet Sitter
sit-stay-play In-home pet sitting & more.LLC
“Your pet sitting, dog walking, poop scooping specialists!”
Serving Muncie, Albany, Yorktown, Anderson, New Castle, Fishers, Noblesville, Indianapolis, Indiana

P.S. Book your pet sitting today or learn more here.