Dating Outside the Box

What happened when I got rid of my relationship checklist.

Tracey Lynn Lloyd

Published November 30, 2018

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I was a late bloomer. My first kiss was at 17, I lost my virginity at 24, and I spent most of my twenties single and dateless. By the time I graduated from business school at 31, I felt like I was late for my personal life. My dad had started asking for grandchildren, and my friends had begun getting married in earnest. So, I plunged into the relatively new world of online dating, on a mission for the perfect husband.

Like a lot of women, I had lists of desirable qualities, ones that I believed would make me happy with a mate, even though I had very little romantic experience. He had to be tall, with a master’s degree and a similar family upbringing. He had to be black, and needed to share my dorky hobbies like swing dancing and karaoke. I thought these were the guarantors of a successful relationship.

Mistakes were made.

My first mistake was trying to hold onto a man who checked all my boxes, but didn’t really suit me. He was a rare combination of ambition, intelligence and geeky blackness that I’d always sought, but he brought out my worst qualities. Yet, I was willing to endure some lying, some cheating and some bad behavior because I wanted to marry someone like him, even if it wasn’t exactly him. Our relationship ended when his side woman confronted me about our relationship. Apparently, their wedding was nice.

My second mistake was like the first one, but with a different man. I dated a computer programmer who dropped out of an Ivy League school to start a tech company. He was 6’4” and the only black programmer I knew, which was intellectually sexy and made for good earning potential. But he disappointed me with his emotional unavailability. He broke up with me via email on my 35 ^th birthday, which proved his immaturity and increased my fear of spinsterhood.

I was single for years after that, and when my 40 ^th birthday rolled around, I was distraught. I’d become my greatest fear: single and middle-aged, going to bed at night with my work and my cat. I was also an only child with one living parent, convinced that my dad would die soon and I’d really be alone. Writing that sentence still fills me with painful anxiety.

But I learned something in therapy called “radical acceptance.” In it, you confront your greatest fears and then ask, “So what?” I was middle-aged, single and childless with an aging parent – so what? I could still date, even though children were probably off the table. And having a healthy relationship could happen at any age, even if it didn’t lead to marriage. My life wasn’t over because I was single, and being single was my reality. I had to accept it and choose relationships for happiness, rather than for an engagement ring.

Today, at 46, I’m dating a man who is the polar opposite of the men from my 30s. He’s smart and funny, but he’s white and he’s kind of addicted to video games. Importantly, he’s very generous, we share the same politics, and we have the same sense of humor. He always tries to make me happy, and that makes for a healthier relationship than any characteristic I sought in past partners.

As a younger person, I wouldn’t have given my new guy a chance because he didn’t come in the right package, and because the I was convinced that the package was the key to my happiness. Now, I’m enjoying the process of getting to know someone whose insides match mine, and I’m confident that knowing how to find that kind of person means I’ll never be without romantic companionship.