Our First House Sit Was Fantastic. And Also Kinda Creepy.

Our first house sit was in Washington, DC during peak cherry blossom season.

For two people who had never done this before, that felt almost suspiciously good. We had a place to stay, perfect spring weather, and one of the prettiest times of year to be in the city.

So naturally, we went full tourist.

The only problem was that we were still learning an important lesson about house sitting:

You do not know what you do not know.

And in our case, what we did not know was that the homeowner’s adult son lived in the basement.

And would be there the entire time.

Fantastic and creepy can, in fact, coexist.

Somehow, they gave us the sit

The part that still surprises us is that the homeowner gave us this sit when we had no house-sitting references.

None.

No history of successful sits. No reviews saying, “Matt and Linda are delightful people who definitely will not adopt your cat and disappear.”

We were brand new.

At the time, we thought, Wow. People are really trusting.

Looking back, we also realize we were pretty trusting ourselves.

Most experienced house sitters would have had more questions. We were simply excited that somebody was willing to give us a chance in Washington, DC during cherry blossom season.

So we said yes.

And mostly, it was great.

We didn’t know what “normal” was yet

House sitting is one of those things that makes much more sense after you have done it a few times.

There are things you learn to ask before accepting a sit. Who will be in the home? How much attention do the pets need? What does a normal day look like? Is there anything unusual about the house or the arrangement?

We did not have that list yet.

So when we arrived and learned the homeowner’s son lived in the basement, our reaction was basically:

Oh. Okay. Cool.

It was not cool.

Nothing bad happened. We barely saw him. But simply knowing somebody else was living downstairs changed the feeling of the house.

We were caring for a cat, so our responsibilities were pretty simple: feed the cat, pet the cat, and avoid losing the cat. That left us plenty of time to explore Washington.

And we explored a lot.

Partly because Washington was spectacular.

Partly because there was a guy in the basement.

Meanwhile, Washington was showing off

The strange house situation and the trip itself existed in two completely different worlds.

Because Washington during peak cherry blossom season was gorgeous.

We took the train to the Tidal Basin and walked into one of those travel scenes that looks almost too perfect in photographs. The cherry trees were in full bloom around the water and monuments, with blossoms in the trees, blowing through the air, and scattered across the ground.

Linda had her camera with her, which meant progress was measured in feet.

Walk a little.

Stop for a photo.

Walk a little more.

Stop for another photo.

We did the monuments. We did the museums. We walked all over the city and did the full tourist experience without pretending we were too sophisticated to enjoy any of it.

We kept coming back to the same thought:

We are staying in Washington, DC during cherry blossom season without paying for a hotel.

This house-sitting thing might actually work.

What our first house sit taught us

The biggest lesson from that first sit was not that house sitting is free lodging.

It was that house sitting is an exchange, and a good exchange depends on knowing what you are agreeing to.

We learned that the destination can be amazing while the sit itself has quirks.

We learned that questions matter.

And we learned that there are things we would want to know before saying yes to future sits.

After Washington, we started asking better questions and paying more attention to what was included, and sometimes what was not included, in a listing.

Our first sit showed us what house sitting could make possible.

It also started teaching us how to choose better sits.

Would we do it again?

Absolutely.

The weird basement situation did not scare us away from house sitting. If anything, it gave us the first piece of experience we needed to get better at it.

And the destination certainly helped.

Washington in full bloom was a pretty spectacular reward for Sit #1.

You never forget your first.

Ours just happened to include cherry blossoms, a cat, free lodging, and a guy in the basement.

Not a bad introduction.

Want to understand how house sitting actually works?

If you’re curious about trying it yourself, start with:

House Sitting 101: How House Sitting Actually Works (Without the Instagram Lies)

We break down the exchange, the responsibilities, what house sitting still costs, and what we think someone should know before accepting a first sit.

With love and laughter,
Matt & Linda

Check out our House Sitting Hub.