Wardrobe Tips for Today's Dating Scene

Here's my official fashion tip for you, the middle-aged dater: Be vaguely slutty

Photograph by Getty Images

Back in the day — and by “the day” I mean 1985, or even maybe 1988, some period when I had a perm and weighed 25 pounds, okay? Back in that day, when I had a date — and I often did, because who wouldn't ask out emaciated "Dancin’-on-the-Ceiling"-hairdo girl — I wore a black miniskirt with something. What I wore other than the black miniskirt was irrelevant, because my legs were rockin’ the house, is what they were.

I can assure you I put 100% zero effort into having those legs; they just came out the end of my body looking like that. I’d eat chili cheese fries at 2:00 in the morning after several hundred beers, and yet the next day, there’d be my slender legs again, all forgiving and supple.

So to show them off on dates, I’d sport the black mini and a stripy Espirit shirt. Or the black mini and a sleeveless tee with something vaguely New Wave on it. I had this T-shirt with a bunch of Barbie dolls on a grill, and it read "Barbie-Q." I could get away with wearing stupid things like that because ... did I mention I looked great in anything, what with my 25 pounds of youthful thin-nity and my wide blonde perm?

Then I got married and stopped caring how I looked and my legs went to hell and I got divorced and I know you’re all smug, thinking, “If she’d kept up her appearance, maybe refreshed that permanent wave, she’d have kept that man.” I wouldn’t have, okay? I promise you. And stop saying things like “permanent wave.” What are you, 94 years old?

The point is, there I found myself, in my mid-40s, dating again and no longer able to get away with slapping on the black mini and some Aussie Scrunch Spray and heading out the door.

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A few years back, right before my first date as a grownup with formerly good legs, I went to Banana Republic. A young girl asked if she could help me. I grabbed her on both shoulders, as though we were in a disaster movie and I was going to tell her she needed to pull herself together. “I have my first date since Clinton was in office,” I told her. “Before the cigar thing, even. YOU HAVE TO HELP ME FIND SOMETHING TO WEAR.”

And you know what? She did. And here is my official fashion tip for you, the middle-aged dater: Be vaguely slutty.

I mean it. And I realize you should not remotely be taking advice from someone who had a "Barbie-Q" shirt in her wardrobe. But through trial and error, I have found this to be true.

Wear just one sexy thing. Show off your okay-I-got-a-little-fat-but-hey!-boobs-now cleavage. Or wear heels a little higher than you normally would. Get some trendy jeans. And for the love of all that is a Real Housewife, don’t do ALL these things at once. Just pick one and go with it. You’ll feel a little prettier. You’ll forget that you spent the last 15 married years in yoga pants and flip-flops.

The point is, if you feel a little pretty and a little daring, fancy special things might happen. Maybe it won’t be true love. Maybe it won’t be true like. But maybe you’ll remember the you that you used to be, combined with the smarter, better you that you are now.