When it doesn’t pay to date

(Sarah Wilkins, For the Los Angeles Times)

We’d been set up by friends, and her stats were promising: mid-30s, attractive, athletic and smart. After the perfunctory call to ensure that we weren’t blatantly incompatible, a date was arranged.

My sister, who lives in Venice (which was where my date and I had agreed to meet), recommended a European restaurant that sounded romantic enough. When I asked her if it was a reasonably priced blind-date place for a guy who’d recently transitioned from many-year company man to new small-business owner, she replied: “It’s reasonable, but who cares? Just split the bill.”

Split the bill? I’d rather eat a box of rusty nails. The feast/famine rhythm of the self-employed has not come easy to me, but I was born hard-wired with some quasi-chivalric code that states that the man always pays for everything. Period.

A few hours later, as my date walked up to where I stood waiting in front of the restaurant, my inner voice instantly said, “Nope, not her.” She was pretty and stylish, but “it” just wasn’t there.


Nonetheless, we went inside together to dine.

When the bill came, she went for her purse. But I pay, always, for everything, even when it’s a woman with whom I have no future. I waved her purse-rooting aside and threw down for the $167 (I guess reasonableness is subjective).

After some pleasant goodbye chitchat at the valet stand and a kiss on the cheek, I made my way back to where I’d street-parked my car (I rarely valet these days). I saw the ticket under my wiper blade from 40 paces. Sixty-eight dollars.

The signs; I always read the signs. But I guess I don’t always read the signs.

(Disclaimer: I grew up in a family in which making the rent — rent, not a mortgage payment — was often a struggle. But I am very aware that any issues I may be experiencing with my dating budget are, as we say, a quality problem. There are people who must choose between buying their medicine or groceries -- I get that.)

Exactly two weeks after the “ticket” night, I went on yet another blind-ish date with a woman I’d met online. I had a good feeling about this one (gorgeous, arty, had a dog), and my newly instituted policy of meeting only for drinks on the first date was accepted enthusiastically.

She was waiting for me when I got there, and I was immediately struck. “Yes,” my inner voice said. We laughed and talked; it was easy, natural. At one point, she told me she was famished, so I called the waiter over, and she ordered one of the specials. “Why not?” I thought. “Get three, go nuts, let’s just keep this rolling.” (Policies are made to be ignored, right?)

The rest of the evening went superbly, and then the check came. I grabbed it and said, “No, no, no, I got it,” when she went for her purse. But she kept up, producing a $20 from her wallet. “No, seriously, it’s my pleasure,” I continued. She explained that she wanted to at least contribute to the bill, and it was only fair, since I didn’t eat.


I almost rejected the notion a third time, but two things occurred to me: (1) She might really not want me paying for her meal so as not to seem obliged or on the hook in any way, and (2) I actually did valet my car that night and her $20 would save me a trip to the ATM. I gave the waiter my card and pocketed the twenty, feeling only slightly weird.

Two days later, after the proscribed waiting period, I left a voice mail on her phone saying how nice it was to meet her and that I hoped we’d talk again soon. Roughly three hours later, I received the following text: “Regardless of the circumstances, if the guy doesn’t pay on the first date, something is wrong. No second date.”


I composed about five replies but sent none. Instead, I discussed the night and the text, first with my sister and then with my shrink. My sister said, “Ridiculous! You agreed to meet for drinks and then she orders dinner and stops you from paying but expects you to pay? That freak can buy her own dinner.”


My shrink had a slightly less zesty interpretation, saying, “There might have been some testing going on there. It could be seen as odd behavior.”

In spite of their words, I can’t help but think I blew it. Of course, her inner voice might have instantly said, “Nope, not him,” and maybe she felt the “man pays” angle was the kindest unkind way she could give me the slip.

I’ll never know, but you can bet that this week when I meet the personal trainer for a smoothie, I’m buying.

Jeff Duncan is a Los Angeles writer who also works in the music industry. He has just completed a memoir, “Road of Kings.”

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