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The first time I laid eyes on a man I’ll call Toby I elbowed a close girlfriend and jokingly whispered, “Dibs!”

Seated across from our friend Dave was a handsome stranger Dave had met volunteering. That evening I learned Toby had many qualities I sought in a boyfriend. Humorous? Check. Shared religious beliefs? Check. Intellectual? Kind? Hardworking? Check. Check. Check. I left the restaurant smitten, hopeful to see him again.

To my delight, Toby became a fast member of our friend group. Playful teasing from Dave confirmed my inkling that Toby, too, felt a spark between us. Before long we found ourselves in the type of friendship that often precedes dating. We gravitated toward one another at group outings, often ending up to the side of the gathering, engrossed in our own conversation.

While I’d never felt particularly skilled at chatting up the opposite sex, captivating conversations with Toby flowed easily. One evening, almost oblivious to the sounds of live music and friends around us, I realized not once during our forty-five-minute conversation had I racked my brain for what to say next. Rarely did I feel so comfortable with a potential love interest. My heart wanted to charge full steam ahead into dating him, but my head hesitated. When he offered to walk me home that night I invited a friend along, subconsciously sabotaging an opportunity for him to ask me on a date.

Despite palpable chemistry and thoroughly enjoying his company, something about Toby was giving me pause. The root of my hesitation became clear at the next group outing. Nestled in a corner booth, again in our own world, Toby described to me a challenge he had undertaken that evening. He was trying to practice more self-control, something he felt was a weakness of his. As the conversation progressed, I realized that he was describing what was giving me pause when it came to pursuing a relationship with him.

In many ways, Toby was a great guy, but perhaps wasn’t living as virtuous of a life as he thought he should. His efforts to better himself were admirable, and his openness about them was courageous. Even so, I didn’t want to date a man knowing that our long-term compatibility was contingent on him changing. Our friendship continued, my head and heart at odds, until a conversation with Dave confirmed my suspicion that Toby wasn’t right for me.

“I’ve been feeling very protective of you,” Dave admitted when I asked for his insight. He spoke those words quietly, hesitant to speak negatively of his friend, but concerned enough for my best interest to share his thoughts. Dave was a trustworthy friend, happily in a relationship of his own. My conversation with him confirmed that Toby wasn’t in a place where we would be compatible long-term. And dating on the hope of change wasn’t what I was looking for.

That summer, Toby and I moved to different states, and our friendship began to wind to a natural end. I wish I could say that my level of affection for him followed logic, but instead it took months to fade as I processed the important lessons I’d learned. Getting to know Toby made me more aware that the checklist of qualities I sought in a boyfriend was a good initial screening tool, but true assessment of compatibility was much more complex. His friendship helped me see that a man could share my most important beliefs on a basic level, but might choose to apply them to his daily life much differently than I did. I learned that while great chemistry was enthralling, it was only one component of the more important measure of compatibility.

A few years and several adventures later, I once again found myself seated across from a man who checked all the boxes on the list of qualities I was looking for in a boyfriend. Once again, I found myself immersed in a conversation for two, despite being in a crowded room. Armed with lessons from the past I kept my heart from getting ahead of my head, though I did entertain the idea of his potential. Immediately upon parting ways I texted a mutual friend we’d discovered for an inside scoop. Unbeknownst to me at the time, the man I’d just met did the same. This time I was met with support from our mutual friend, a promising sign.

In the early weeks of dating that ensued, I saw that this man’s virtues extended beyond my checklist. The thrill of the chase and unknown that had been present with Toby was instead replaced with the peace of intentionally getting to know a man who clearly communicated his interest. Initial chemistry grew into a deep sense of comfort with one another. As weeks turned into months, his actions showed time and time again that his moral compass matched mine. I never had to wonder whether he would make a good husband, I could delight in the confidence that I knew he would be. But that’s another story.