An illustration of a person in front of a car looking through binoculars with dollar signs in the lenses.
Illustration: Giacomo Bagnara

Though I’ve never met her in person, my insurance agent, Carol Ann, has been a constant presence in my life for more than a decade. She was one of the first people I called after I got engaged. My spouse and I didn’t make the down payment on our dream home until we had her blessing. When my father died, Carol Ann offered her sympathy, along with patient guidance on settling his estate.

When life gives us lemons, some people make lemonade. What I make is a call to Carol Ann.

We speak infrequently. When we do, it’s usually about things I don’t discuss with anyone else and, frankly, would rather not think about. Like whether my spouse could afford to keep our house if I were hit by a bus. In other words, we talk about the big stuff.

And a funny thing happens when you seek someone’s counsel about intimate fears like death and lawsuits and losing everything you hold dear. It creates a bond, and an inclination to forget the fact that our relationship, when it really comes down to it, is purely transactional. She provides me with the protection from peril and penury that I need; I help her meet her goals at work and maybe—for all I know—win a trip to Cancún.

But like many relationships, ours is greater than the sum of its parts. Carol Ann is a source of security in a world that can feel dangerous, and she’s a skilled navigator of a sphere that is foreign to me.

Which partly explains why I can’t remember the last time I shopped around for lower rates, in spite of the fact that CR experts say it’s the only way to make sure an insurer isn’t taking advantage of my loyalty. The truth is, I don’t want to break up with Carol Ann.

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Still, protestations to the contrary notwithstanding, most loves do have their limits, and being taken advantage of is one of mine. So when I learned that CR was working on an article with The Markup about “personalized pricing” in insurance rates, which could leave some consumers vulnerable to paying higher premiums than warranted, I was dismayed. When I learned that my demographic—middle-aged customers—was potentially on this “suckers list,” my indignation displaced any sneaking sense of infidelity, and I got busy finding out what the competition had to offer.

I was quickly reminded of how tedious and time-consuming insurance shopping can be. I have renters, homeowners, auto, and umbrella policies, and needed to speak to three separate representatives to get quotes on all of them at two companies. At another company, one representative was able to provide quotes for all those policies, but only after I’d spent more than an hour on the phone with her. (On the upside, it was anything but boring: While her computer was crunching numbers, the agent gave me travel advice and movie recommendations, and told me how she and her mother had decades ago contracted whooping cough from a nurse who assisted in her birth, which led to their being quarantined and featured in the local newspaper.)

Requesting a homeowners quote from an online-only algorithm-based insurance provider was as fruitless as it was painless: It took 3 minutes to enter the information required and only an instant for its bot to let me know my home didn’t qualify for coverage.

After a few hours of research, none of the four insurance companies or the broker I contacted could offer a better deal than the one I’m getting from Carol Ann. One came close, but the others were significantly more expensive. I’d always hoped that Carol Ann was charging me fairly for my insurance coverage. Now that I’m certain she’s giving me a square deal, I trust and value her even more.

I don’t know what I would have done if someone else had offered me a lower price. What I do know is that it’s better to weigh all your options than it is to simply hope that you’ve made the right choice—even when it turns out you have.

Editor’s Note: This article also appeared in the April 2020 issue of Consumer Reports magazine.