The Washington PostDemocracy Dies in Darkness

How do you woo someone when you’re still figuring out life?


Doubt is human, but it isn’t sexy.

I didn’t blow my chance with this woman because there wasn’t chemistry. I didn’t blow it over a lack of common interests. I blew it because I’m still figuring out my life. And women want men who have it figured out, or at least appear to.

Doubt says: “I’m not sure about me.” Which can also say: “I’m not sure about you.”

We met in a bar. We bumped waists while strolling to a friend’s hotel. She wrapped an arm around me. I pulled tight. She tripped on the escalator; I caught her at the waist. A Band-Aid, a bed, a kiss. The next day she flew back to Austin and put 2,000 miles between us.

Texting. Weeks of banter. Then a day of nothing. A couple more days. Her name bumped down the contact list.

I visited her in Austin, just passing through on my way to a new job, new career, new Zip code. We spent an afternoon taking in the city sights. Perched on a wall, feet dangling, we talked about relationships. The failures. Was she really she open to something meaningful? Maybe not, she wonders. Someone could sweep her off her feet, she admits.

Go ahead, I said to myself. Sweep away.

But I was fumbling about, having ditched the steady office job to join the creatives on the Left Coast. I traded answers for questions, salary for freelance. Stability for solitude.

The doubt those changes created rubbed off on my love life, producing a more vulnerable, less cool and confident version of me.

We had beers and talked about our futures. I’d read her work, enjoyed it, but she said she didn’t want to be a writer after graduation. What’d I miss? We had connected over literary ambitions, and now I felt disconnected.

We went for pizza. I brought up William James, and her eyes wandered. Entertain her, I thought. I wasn’t just doubtful; now I was boring.

I used to be quite clever in conversation – quick with a quip or a pop culture reference. I had a map for every fork in the road. Books on psychology for personal problems and personal development. Emotional intelligence [retrieve book from bookshelf]: Heard of Daniel Goleman?, I might ask.

As I was leaving, she leaned against the mantle of the fireplace. It was a moment to cross the room. There’s no art to room-crossing; it just takes guts. But I hesitated, and missed the opportunity.

Perhaps I could be my quick-witted, gutsier self again if I tightened up my resume, made a few calls, dropped this silly writing business.

In my experience, women want love interests with goals, but not ones that don’t pay the utility bills. Having your life together matters. That usually means law degrees or middle management. Or if you’re one of those creative types, it means book deals and published works. You’re working on a novel? How cute.

Women want winners, especially once they’ve reached their 30s. Without a steady job, what do I have to offer? At that point, I’m selling hope. I’m a gamble.


That’s all right, I think to myself.

I wasn’t lucky enough to find my calling in high school or college, even graduate school. I stumbled onto it in adulthood. I’m playing catch-up now. It’ll be a while before bulging diamonds and red-doored homes, before funny-sweater Christmases and let’s-play-mommy-and-daddy.

All this doubt and delay begets more doubt, more delay.

I’ll be back in high places again. And maybe, when she visits in February, I’ll be sure about me, which means I’ll be sure about her.

I don’t know, though. I have my doubts.


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