Lunch with Caren, a co-worker, was winding down. She had invited me to lunch, ostensibly to talk shop. We were sitting in a booth at The Rail, one of the better places to have lunch in Ft. Myers. It was a scorching hot Thursday in August.

“So you think we can get enough psych hospitals to join the network,” she asked. We had been discussing a preferred provider network for mental health treatment. Caren was a sales manager tasked with selling a special health insurance rider to local businesses and labor leaders.

“It will take about three months, maybe more. I’ll put some pricing together, but I can tell you, we won’t get big discounts.”

“Well, Jake, that’s your department. I’ll leave it to you,” she said. The server brought the check. I reached for it but she beat me to it. “Don’t worry, I’ll expense it,” Caren said.

I smiled, “God bless the subscriber.” It was a standard inside joke at our non-profit company.  We were quite frugal with our subscribers’ money, but most of us managed to feel a little guilty when they treated us to lunch.

“Jake, can I ask you a question?” I nodded. “I want you to be honest, please, ok? Why don’t men find me attractive?”    

I never saw it coming. Caren was not a pretty girl. She wasn’t exactly homely, but close. She was also bright. She could be funny. And her colleagues respected her. I knew it wasn’t a come on. I was incurably married and she knew it.  I was at a loss for words.

She sensed my discomfort. “That’s okay, forget I asked.”

“No, no, your question just surprised me. Tell you what, let’s have lunch again next week. I’ll give you an update on the psych hospitals and then I’ll answer your question,” I said. “But Caren, you asked your question like you’re stating a fact. I’ll think about it, but that doesn’t mean I agree with you.”

“Okay. Thanks for saying that.”

I had a busy week. I didn’t get much time to think about Caren’s question much less a good response. I mentioned it to Dennis, my best friend since we were kids. I told him what Caren asked me as he was taking a good swallow of root beer. He laughed so hard he got root beer up his nose and on his shirt. “Tell her she’s beautiful,” Dennis said. “Tell her you fall asleep most nights thinking about her. You’ll be golden.” Not helpful.

I asked Elena, a trustworthy co-worker, what I should say. She made me repeat Caren’s question twice, insisting that I recapture Caren’s tone. “Cancel the lunch,” she said, “even if you have to call in sick that day.”

“Why?” I asked.

She smiled and said, “Trust me. You don’t want to get into a discussion like that with her.” That’s when I knew I was on my own.

When Thursday came I realized that Caren and I had not had any communication since our luncheon. Maybe she was giving me an out. If I didn’t reach out to her, it would be forgotten. I called her an hour before we were scheduled to have lunch.

“We still on for lunch?” I asked.

“Yes, if you want to we can.”

“I have an update for you on the hospitals,” I said, trying to sound nonchalant.

We went to The Rail again. I gave her a quick update and waited. She seemed nervous and was very chatty. Obviously, she was not going to bring up the subject unless I did. And to be honest, I was sorely tempted to pass. I noticed she was dressed better than she was last week. More makeup on too. I had to say something. But what?

“Caren, last week you asked me why men don’t find you attractive. Is it fair to say you haven’t been going out much lately?” 

She nodded her head. Her eyes had a distant look to them, like she was preparing to hear something very painful. I was operating on pure instinct. “Let me ask you, Caren, do you think you’re pretty?”

She shrugged. “Not really.”

“Maybe that’s a good place to start then. If you don’t think you’re pretty, why should available men think you are?”

She seemed surprised. “Good question, I suppose.”

“Listen, I see this a lot. I think women tend to dress, at least a little bit, based on how attractive they think they are. Even some very attractive women dress like they rolled out of bed and wriggled into whatever they found on their bedroom floor,” I said. “Maybe it’s a self-image thing.

“Do I look like that?”

I opened my eyes as wide as I could and said, “Not today.” It had the intended effect. She laughed.

“I’ve also seen women who aren’t very attractive dress and carry themselves as if they were constantly being chased by fashion magazines to model for them.”

“Are you saying men would find me more attractive if I changed the way I dress?”

“What I’m saying is looks are only one piece of the puzzle. What you wear and how you carry yourself matter just as much, if not more, than your looks.”  

“But pretty women don’t have to worry about those other things, right?”

“Doesn’t matter. You want to meet a nice guy and have a meaningful relationship. If you have to do a little bit more than Jennifer Aniston does to attract a guy, that’s not a catastrophe.” 

“Maybe you’re right.” The server arrived with the check. I felt so good I let the subscribers off the hook.