My Outfit's Bad First Impression Didn't Prevent a Second Date

How should you dress for a blind date? High fashion and ritzy? You may look like a snob and be off-putting. Sexy and hot? You may be sending an invitation you don't want to honor. Professional? Sporty? Everyday wear? Every choice you make may be the wrong one when you don't know who you'll be meeting.

We met through the personal ads and I knew he was a computer professional, from California, like myself. Not to malign California computer geeks, but we're generally not the targets of haute couture ad campaigns. I decided to try for a Friday fun look- fashion jeans and a Hawaiian-style shirt. Bananas, pineapples, palm trees on leaf green. Really, it wasn't too loud. It was clean, it fit, there were no holes in the knees, it showed enough but not too much of my figure. The guy should be OK with it, right?

We met at one of my favorite Austin restaurants. I explained to the hostess that I was meeting a blind date and she pointed behind me. I turned and there he was, sprawled on the bench, the quintessential '50s high school geek. White short sleeved singled-pocketed polyester shirt, kinda shapeless beige jeans, sneakers, hair parted on the side and slicked down. All that was missing was the pocket calculator and glasses.

Well, we survived and even enjoyed the first date, because many others followed. In fact, it was several years later that he told me that he nearly ran when he saw that pineapple shirt. And apparently my initial expression was not very welcoming, either (hey- he was practically LAYING across that bench!). I didn't believe him, I kept wearing the shirt, even though I inspected his closet and got rid of as many of his short sleeved polyester geek shirts that I could. Finally, during a closet clean-out day when he pleaded with me to add that green fruity shirt to the pile, I realized how bad a choice I had made for that date.

The shirt is long gone. I kinda wish I had kept it, to photograph for this article- then you could tell me whether YOU'D have given me a second chance. But he did, and still does, after 15 years. So it couldn't have been too bad a fashion disaster, could it?