Uh, That’s Not What I Meant by “Date Me”


A while ago I decided to try my luck at internet dating. It was neither a failure nor a success, and I soon lost interest. The only lingering evidence is a leftover profile at OkCupid, mostly because I’m too lazy to delete it. I still get the odd message from guys who like my smile and think we should chat. It’s what you’d expect, the sheepish norm of first contact between potential paramours in the digital age. What you don’t expect to get, however, is unsolicited style advice.

I am one of the lucky few.

The new message announced itself with a cheerful digital chime. The sound was misleading. It read: You are cute, but you should work on your wardrobe. Makes you look much older than 22. Just thought I’d help you out.

You know that alarm sound that Uma Thurman hears in Kill Bill? That’s what I heard. I wanted to send back a string of expletives, shredding his opinion of my personal style. He was totally wrong… right? Just to refresh my memory, I looked over my pictures to see what sort of “dowdy” ensembles he was criticizing. One was a ’50s style strapless dress with a sweetheart neckline, covered in a pattern of prize ribbons. Another, a silk blouse with a whimsical print of chairs, leaves, and umbrellas. In the third, a black dress with drawn cassette tapes unspooling in every direction. All of them are very cute outfits; none of them requiring a stranger’s intervention.

But a flash of self-doubt wracked me. My insecure inner 12-year-old suddenly wondered if maybe people saw me that way. Did I really come off as stuffy and uptight? It took years for me to feel comfortable in my skin. My shape never fit the American Eagle model that was popular when I was in high school. More than once, I wept in a change room, unable to navigate a pair of pubic-zone-grazing jeans and, rather than turning me into a Seventeen-queen, trendy mini-skirts just highlighted my stumpy torso. It was crushing. But creativity eventually took the place of insecurity. I went after vintage silhouettes and tailored looks; maybe they looked “older” to some but they made me feel self-assured. That’s when I decided I wouldn’t let people make me feel silly for what I put on my back.

So why did I let this man’s comments send me into a tailspin?

With his comment, he didn’t just insult my clothes—he insulted the image I had of myself. I wasn’t fishing for compliments, but the pictures I chose were of a confident and beautiful me. His offhand offer to improve what I thought was me at my best bruised my ego and made me question what the world saw when they looked at me. And although I want people to like me for who I am, the voice of the ostracized pre-teen in my past was suddenly asking, should I change?

If I were to slide off the high road and come face to face with my insulter I’ve considered a barb or two I could hurl in his direction. I’ve even thought of the outfit I’d wear: a red and white iris-printed sundress with a button front, cap sleeves, and a crinoline underneath. I would lower my cat-eye sunglasses, my neck scarf fluttering a little in the breeze. In my drollest Katherine Hepburn voice, I’d say: “Hey buddy. My wardrobe doesn’t need help. As for your personality, I’m not so sure.” But what would be the point? I know who I am, I know what I like, and as trite as it sounds, I’m confident I’ll meet someone who appreciates me just as I am.

I wonder how his quest for true love is going?

text by Cayley James