09/03/2013 05:06 pm ET Updated Nov 03, 2013

Miss Hawaii Uses the F-Word

Years ago I went on a date with a former Miss America contestant. Wait, hold on. Is that as big as these fonts go?


Okay, that's better.

My friend's wife was shopping for clothes and the saleswoman was really gorgeous. They got talking and it turned out the saleswoman was new in town. She had come to New York to pursue fame after her Miss America appearance. My friend's wife then proceeded to set the two of us up in what's generally considered the single greatest act of human kindness since Bill Gates donated $10 billion to the Third World.

Fortunately, it just so happened I was in the middle of 15-year dry spell, so I was free. Suffice it to say Miss America contestants weren't exactly lining up to go out with me at the time. Crazy women on the verge of going back to their ex-boyfriends? That was usually my demographic. I couldn't keep those kind of women away. Well, until they went back to their ex-boyfriends, of course.

But I digress.

To protect this woman's identity, I'll refrain from telling you exactly which state she was the Miss of, but I will say it's a state with lots of stunning women. Seriously, attractive women are one of the things you think of when you think of this state. We're not talking Miss Delaware here.

I'm dying to tell you. It'd really blow you away. What the hell, she was a Miss Hawaii. Excuse me...


I was nervous approaching the bar. I mean this woman was basically voted the most beautiful woman in Hawaii. When we met, however, the nervousness disappeared. She gave a big smile that put me right at ease. Looking back, it occurs to me that a pageant winner probably knows how to turn on a fake smile, but it felt nice nonetheless.

We sat down and began that awkward first-date dance of attempting to find out what things we had in common. After about 40 seconds we had our answer -- nothing.

At the time I was a writer for David Letterman. I spent my days making caustic jokes surrounded by cynical nerdy guys. She was from a world in which bikini-clad women talk about their plans for world peace with a straight face. So obviously we were at opposite ends of the irony meter.

But that was okay. She was very sweet and down-to-Earth. Even though we were very different people, we still had a really nice chat. In fact, it was great. Maybe I had been cynical too long. Maybe it would be good for me to spend time with a sunny, optimistic person. I dare say we were hitting it off. She told me great backstage stories about who always hogged the mirror (I'm looking at you, Miss Texas).

As the night wore on, somehow we got talking about gay men. I forget exactly how we got on the topic, but I'd wager it had something to do with former pageant host Lorenzo Lamas.

One of things I have learned over the years is that when a person prefaces a statement with "Listen, I'm not a racist, but..." they should just shut up right there. Nothing good will come from whatever they are about to say. If they are a politician or a football coach, there is a hastily arranged press conference in their future. Reverend Al Sharpton should cancel his dinner plans, because he's going to be on MSNBC all night.

Similarly, as soon as my date said, "I have a lot of gay friends, so I can say this...." I should have asked for the check. I don't care how many gay friends you have, I'm 99% certain you can't say whatever it is you're about to say. So don't say it! Please don't say it.

She said it.

She used the F-word. The other F-word. Yup, that's the one.

While I was still reeling from the initial blast, she then used it again. I actually found the second one slightly more forgivable because she was Hawaiian. I figured it might be one of those words Hawaiians say twice like pu pu or Wikiwiki.

Still, she shouldn't have said it at all. Neither the pageant judges nor I would have awarded her a high score on the "poise" portion of our date.

After we finished our respective Mai Tai and Bud, I ended the date with a noncommittal (but charming), "Hey, I'll call you some time." Thus began the internal debate. The moral part of me knew that I couldn't see her again. On the other hand, Miss...freakin'...Hawaii.

I spent the next few days trying to arrive at a workable compromise. Maybe I could go on another date with her, but just make sure the topic of homosexuality never came up--sort of a Don't Ask, Don't Tell solution. Ultimately, though, I could not bring myself to call her.

So what does that say about me? What word do you use to describe a guy who turns down the possibility of sex with a former Miss Hawaii for moral reasons? "Admirable"? "Decent"? Perhaps, but I think I have a pretty good guess what word she'd use.

Tom Ruprecht is author of the new Amazon Kindle ebook "This Would Drive Him Crazy: A Phony Oral History of J.D. Salinger."