Published: February 10, 2015

The CEO was 20 years older than me, not my typical quarry. But any man who writes an engaging, funny, complex flirt on a dating site gets due consideration. After a few volleys I wanted to meet. I was eager even to hand over my Sunday afternoon.

CEO: Are we on the record?
Me: You’re not a cabinet secretary. We’re on the record.
CEO: I read your dating column.
Me: What do you think?
CEO: They’re really good.

I’m easy. Compliment my writing, and I will let you get me drunk. He ordered a bottle of fancy Bordeaux and pulled a tiny gift out of his pocket. The only men who have ever given me presents on first dates were on reality TV, and it was completely fake.

I untied the ribbon and ripped off the wrapping paper. It was a refrigerator magnet that said “Gentileza Gera Gentileza.”

Me: Gentiles beget gentiles. You gave me a message from my dead grandfather.
CEO: Kindness generates kindness. It’s graffiti all over Rio. Be kind when you write about me.

The CEO was a former journalist turned corporate kahuna. He had the good sense to get out and earn a salary with many zeros in it. I fiddle while Rome sizzles. But oh, does he miss working a beat. We emptied our wine while he reminisced about reporting like a college football star reliving some 80-yard pass.

He was good company. I rarely want a second round on a first date. He ordered another bottle and gave testimony.

CEO: I think cluelessness is underrated.
Me: What does that mean?
CEO: You became a journalist because you were clueless.
Me: A question and a pen, and now I’m broke.

I was tipsy. He ordered food.

CEO: My divorce has been such a journey; I’m learning so much.
Me: This is your first time in therapy.
CEO: I’m loving it. See? Cluelessness!

He was generous, funny, smart, Jewish, every key thing. There was not a hint of romance.

CEO: I spent 30 years in a sexless marriage.
Me: Why did you stay?
CEO: Cluelessness.

A bottle of wine is a serving size, and we had two. He was not making more sense.

CEO: Next time I’m going to marry someone who takes care of me back.

Then he came into focus, somewhere at the bottom of that second bottle.

This is axiomatic: When you love someone, you take care of them. But I’ve had haunted boyfriends – Hydes and Holocaust men – and I was too besotted to see they never bought the next round, didn’t caretake back. They mowed me down when they ran for the door; they were extremely busy chasing zombies.

Me: That’s everything. That’s what I’m looking for: I want to take care of the guy who takes care of me back.
CEO: You were clueless. Now you aren’t.

Dating is mostly miserable most of the time, but the CEO and I would be friends.

CEO: You realize your column is just the Odyssey, don’t you?

I met a man who wasn’t a monster. It gave me hope. Maybe someday I’ll be sailing home.


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