I Met A Guy Who Checks All The Boxes, But ...

There's just something that isn't quite right.

By

Robin Westen

 
Published March 28, 2024
Long list of checked boxes on a clipboard with the bottom of the list on fire.
Justin Poulsen

Relationships are tough. They can break your heart, crush your spirit, drain your energy, and, worse, make you second-guess yourself. But I’m a resilient woman. A few months after breaking up with an uber-handsome but impoverished and bitter artist, I sat down one evening with a glass of wine and thought long and hard about what I really wanted in a guy. “Next time,” I vowed, “I’ll be sensible.”

After meditating on priorities, I decided on the following:

A professional who is stable, smart and financially sound; a compassionate, kind and calm man, close with his family, sophisticated and well-traveled, who enjoys physical activity and appreciates literature, art, music and films. Also, he has to like dogs.

Was this too much to ask?

That night, I posted on a popular dating site and envisioned my future partner with an intensity Oprah could applaud. Surprisingly, the conjuring worked. Along with dozens of mismatches, the profile of a man named James, who ticked all the boxes, appeared on my laptop. His posting described a career in medicine, lots of travel and an elegant lifestyle. He enjoyed exercise and loved his family. His perfect grammar was a boon.

I sent him an enthusiastic message that included my email address.

The following morning, “James, MD,” replied, suggesting we meet. Before responding, I reviewed his profile on the dating site and realized I was so focused on the list that I hadn’t paid attention to his picture. James was far from my usual lanky rock-star “type” — he was on the short side, with a balding pate. I quickly lectured myself about being hung up on looks, which now seemed ridiculous at my age (a middle-aged woman).

A few days later, James was waiting outside a wine bar wearing a navy blazer and crisp white shirt; it struck me that he looked more like a well-pressed prep schoolboy than a full-grown man. But his relaxed confidence and sophistication proved me wrong. He ordered a bottle of pricey red, easily engaged in conversation, spoke openly about his career, interests and family, and was curious about my life. He flashed several thousand-watt smiles and had a cute habit of lifting his left eyebrow if he found something amusing. I decided he had a nice face. After two hours of a perfectly pleasant time, he hurried off to meet his adult daughter for dinner, but not before picking up the bill.

“No Fourth of July fireworks,” I thought to myself. “But he seems to be a wonderful man.”

That was six months ago. James has shown himself to be thoughtful, kind, steady and generous, an eager and imaginative sex partner and an all-around good guy who is also affectionate with my dog. That’s a big plus. But the sparks still weren’t flying.

Despite how perfect he seems in so many ways, I’m not falling in love. Instead, I worry we’re on a slow and steady crawl to the romance-killing friend zone or a complete dead end. The problem is that I’m not ready to lose this nice guy, and it doesn’t seem like James wants to let go, either. That’s why I’m asking myself, “What’s going on?”

Is it really my list? My mother may be waltzing in heaven because I’m dating a sweet, smart doctor, but could this be her dream come true, not mine? Qualities or positions in life that our parents, friends or culture tell us are to be prized might not suit me. I’ve always dated artists; maybe there’s a reason for that. Or maybe it’s a pattern worth breaking.

Could our chemistry take longer to ignite? Just because I don’t have to still my beating heart or deal with butterflies in my stomach, does that mean our relationship won’t heat up over time? Is coming to a slow boil even possible?

Should I turn the kaleidoscope? I might be focusing too much on trying to find the key to James’ emotional connection without working on my own. What if I shift my focus on what I can do to give the relationship its missing oomph?

And those walls? I tend to put up walls and James appears to do the same. We have a lot of relationship history behind us. Could we be hesitating because of our past experiences? What can we do about that?

Am I confusing drama with attraction? My past relationships have been filled with passionate decrees of burning love. James is steady, thoughtful and withholding. He’s never expressed his feelings toward me, not even an “I like you.” Giving voice to his emotional life is definitely not his strong suit. Are the other endearing aspects of his personality enough?

Maybe it’s not meant to be? There’s a real possibility that we’ve given our all to this relationship, and it’s time to move on. The truth is, we’ve been awkwardly dancing around the elephant in the ballroom. Should we stop the music and have an honest and direct talk? This might be the right moment to bow out.

I was pondering all these possibilities when I met my friend Deborah for dinner. She had just returned from her summer upstate and was finally back in Brooklyn, looking relaxed.

“So, how’s James?” she asked, eager to catch up.

“Eh … about the same,” I said, hearing the disappointment in my voice. Then, I went on to discuss my recent thoughts about the relationship.

Deb listened to the list without reaction until I got to the part about James’ withholding expressions of emotion. Suddenly, as if plugged into an electrical socket, she yelped: “What?? After all this time, you can at least expect that much from him,” she bellowed.

“Expect.” I rolled the word around in my mind like a marble. It’s possible that the real problem isn’t James, but my expectation of who James should be or how he should react. As Brené Brown says, “Expectations are resentments waiting to happen.” That seemed to be what was brewing.

So, I’m giving our relationship another chance, trying to change my perspective and release expectations. Probably not an easy task. On the other hand, why put so much attention into what’s around the corner? Or focus my energy on what James is not? It’s a tall order to try and stay in the present. But if I can do it, maybe I’ll be able to fully appreciate James for who he is — a wonderful man.

Have you ever met someone who checked all the boxes but something wasn't quite right? Let us know in the comments below.

Emmy award winning writer Robin Westen is a former sex advice columnist, author of more than a dozen books and has written feature articles for numerous national magazines as well as for websites.