For almost three years I plugged away at online dating, with minimal success. To my mother’s surprise, I met a lot of forty-something men who were willing to go out with me. Despite my law degree (an apparent turn-off for many males), my daughter’s young age (not a plus to a man with an empty nest), and most importantly, Katie’s autism, a decent portion of age-appropriate men were willing to give it a shot.

I had many first and second dates. (This part did not surprise my mother.) Beyond that, the numbers dwindled. Of the few who stuck around, only two met Katie. One fled almost immediately—citing a sudden realization that he wasn’t ready for a relationship (which may or may not have been true)—and the other lasted eight months until it petered out

For two glorious months, I juggled three men. There were also dry spells. I tried to treat dating like I do writing, embracing rejection as part of the process. It was hard, but I kept at it and didn’t take anything personally. I knew that like writing it was a numbers game. If I sent out enough essays/messages, eventually something would stick.

Or at least that’s what I told myself.

After nearly three years of dating, I was burnt out. I met an interesting guy (an actor turned high school teacher) this past summer, but when that relationship went nowhere, I nearly threw in the towel. Then I received four back-to-back emails with new potential “matches.” And there he was in the last email: a man who took my breath away.

He’ll be short, I thought. Cute guys are, more often than not, beneath my minimum height threshold (i.e., shorter than me). I clicked through, and amazingly, he was six feet tall. Even better, he had a master’s degree and was wearing a suit. I love, love, love a man in a suit. Plus he was divorced but had no children (avoiding the awkward “when you wrote nine you really meant nineteen, right?” conversation).

I read his profile, and while brief, it contained no glaring spelling or grammatical errors and was both witty as well as sincere. I turned to the questions, and the more I read, the more I liked him. He was smart, funny, and well-traveled. He thought it was okay for gays to marry and adopt, believed in climate change, and recycled whenever possible. He didn’t think a woman was obligated to shave her legs or change her name after marriage. He seemed thoughtful and compassionate. He liked to read.

I looked at his photos, and when seen full-sized, I realized he was better looking than I’d initially thought. He’d played both baseball and football at Stanford. I studied his headshot. This guy could date anyone he wanted. He wouldn’t choose a frazzled single mom like me. Or would he? I read his essay again. I could feel my confidence draining away.

Luckily for me, I had just participated in an awesome risk workshop offered by my friend Amy Christensen. (I love, love, love her business, Expand Outdoors.) At the end of the session, she had challenged us to take twenty-one risks for twenty-one days. “Small ones,” she said. “Fun ones. The point is to build your risk muscle.”

I looked at the photo again. Something told me to take a risk. I sent a flirty one-line email because I figured I’d never hear back.

To my amazement, he responded almost immediately. He said he loved my profile and wanted to know me better. He included his phone number and requested mine. This was an alpha male move that probably would not work for many, but one that I found deeply appealing. We scheduled a phone call and talked until the sun came up. The next day, we had our first date. We haven’t stopped talking since.

Was the risk (and the wait) worth it? Oh hell yes.

Until next time,
Cynthia Patton