An editor at Esquire magazine asked me why a certain reader’s profile wasn’t getting the desired results. On the surface this 39-year-old, good-looking guy with a great life/job/future seemed like Mr. Perfect.

I gathered eight women aged 23 to 35 (his desired range) and gave them his profile and two others of men around Mr. Perfect’s age (the two others were added to the mix so the women didn’t know what I was up to). I asked them to write down their first impressions on all three. Mr. Perfect didn’t fare well.

Here’s what the women said: “He’s arrogant and trying to portray himself as if he’s not.” “Picky.” “Pathetic.” “Trying to be a hero.” “Too much pressure.” “If you want a hoity-toity chick just say so.” Four of them said, “Cocky.” And when one said, “High-school jock,” they all cheered. Why was Mr. Perfect coming across as alarming rather than charming?

What was he doing wrong? Lots. His profile featured an obnoxious username (perfect4U) and hook (“You may think you’re one in a million, but in this world that means there are 6,000 people just like you”), an intimidating list of his abilities and brilliance (hotshot executive career, handyman supremo, adored by animals, every sport you can think of, exercise five times a week, etc.), and a tyrannical list of demands on his date (bold, assertive, brainiac, Bachelor’s or PhD, skinny-dipper, non-smoker, sarcastic, and on and on).

If you look at each of these components individually, none is unreasonable. In Mr. Perfect’s favor, he certainly knew what he wanted. It was the bigger picture that was torpedoing him. He may have been a great catch but he took himself too seriously and most important, he showed no weaknesses, no poking fun at himself. Mr. Perfect needed a springboard. If he’d just said something like “I know I sometimes come across as a bit arrogant or pushy, but deep down I’m just a real softie who’s excited about life,” he’d have shown his human side. That’s the side people want to connect with.

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