Newsletter August 2019

Dear Fellow Travelers, 

Time sure does fly when you are Dating like a fiend! We have now been Dating America for two whole months and loving almost every moment! 

We’ve gotten lots of questions about the logistics of what we are doing and, in particular, the logistics of housing and lodging. If we had to guess, we imagine that underlying the logistics questions is the following sentiment:

  • How the heck can you afford this?

Fear not, fellow travelers, your answer is coming! 

For us, house sitting has been an answer to the potential financial strain of Dating America. House sitting is where homeowners entrust their property and possessions for a period of time to us, their “house sitters”.  We signed up for several house sitting websites that match homeowners with potential house sitters:

We set alerts for each site so that we are emailed when house sitting opportunities without pets and in the United States are posted.  We do spend time daily sifting through the opportunities as the “best” jobs get snapped up quickly. 

Most house sitting opportunities require pet care so we typically jump on those that do not involve pet care. We have unpredictable work travel and I have allergies that do not allow us to care for pets, but if you could, it would open up a huge wide world of opportunity! We’ve noticed so far that the listings that do not include pet care tend to be longer house sits. This, of course, has pros and cons to it. Right now, we are committed to house sitting in Colorado Springs for a total of two months. Colorado Springs is not right for us and had we not been house sitting, we would not have stayed this long. However, as we see it, we are using Colorado Springs as a jumping off point for trips to lots of different places around Colorado. It is a trade off: we lose some flexibility and spontaneity but gain a local perspective and, hey hey hey, free housing. 

House sitting is considered an even exchange: we look after the house while the homeowners are gone and the homeowners give us a free place to stay. There is no money exchanged. For us, it has opened up a lot of possibilities and we are staying in places we otherwise wouldn’t have. It also allows us the vantage point of a local. We can see what it would be like to live in a particular neighborhood and town. 

Of course, such arrangements are built on trust in strangers. This might make you cringe, but think of all of the times that you’ve trusted strangers–with Uber, with Tinder, with the person making your food at a restaurant. I found one of my best friends on Craigslist, even! (it was via a Craigslist ad for a roommate, but saying that we connected on Craigslist makes for a better story!) We have opened our house to strangers as AirBnB hosts, too, so this seems easier–we don’t have to live with the homeowners! 

If you would like to sign up for one of the house sitting websites, let us know. Our referral can get you a helpful discount. Do you or someone you know need a house sitter? Connect us!

So, where are we now? Believe it or not, we are cheating on Colorado Springs with a quick jaunt to Santa Ana and Carlsbad, California. Cas has a few meetings for work out here and I decided to tag along. If you are worried about flexibility with house sitting, worry not! Good communication with the homeowners is critical–we just keep them informed of our side trips and little jaunts! You can read more about our recent jaunts around the state! Vail! Breckenridge! Salida! Grand Junction! Fruita (we walked mid-date!)! Glenwood Springs! And, while not a potential for a place to live, Great Sand Dunes National Park!

Our list of places to date keeps growing! In July, we took a suggestion from someone we sat next to on an airplane (Madison, WI) and from a bartender (Glenwood Springs, CO). Surely you know us better than seatmates and bartenders. Do you have any suggestions as to where we should live? We are all ears!

Happy Trails, 

Caitlyn + Cas

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