Finding the perfect compliment isn’t a riddle at all. It’s not as though there’s one for every person at every time. It’s a matter of finding the right moment rather than insisting on one.

The quote above is from a really, really great piece by Tom Chiarella titled “The Perfect Compliment.” Tom goes on assignment trying to come up with the perfect compliment (if it exists). In the beginning, it’s all a numbers game to him: he encounters strangers and dishes out one liners: “Nice Shoes. Great tie.” One day, he delivers more than 1,000 compliments…

But then, as his observation of compliments grows, he re-engineers his technique. As he writes:

If a worthwhile compliment needs anything, it is the weight of realization behind it. So I fell back, watched people go about their jobs, the quality of their interactions, the way they looked at their reflection as they walked the street. I registered. And I learned, or started to learn, that a compliment is a partnership, because the pleasure of giving it lies in its effect upon the person receiving it. What I’d been doing was little more than a salesman’s trick, poorly played. I’d succeeded only in making myself bold enough to broadcast my judgments — dry little seeds spun out on the lawn of humanity — on the fly. I had to risk a little connection.

His compliments become more interesting and from the heart:

All I can say is, that is a classy umbrella. It looks old-timey and right for you.

My mother always wanted me to wear a corduroy coat like that. Now I see why.

Near the end of his adventure, Tom’s decision was to deliver one genuine compliment, one that would be heartfelt but also move the recipient:

In the end, the compliments I came up with were tailored and quirky in the best way. Most of all, they were thorough. I liked delivering them. I enjoyed plumbing the reactions. I sometimes considered for days what I would say before delivering one. Or I’d run after someone for my one chance to say what needed to be said. I’d sit in the broad doorway of the coffee shop for an entire day, feet in the sunshine, shoulders in the cool. I did not go on the hunt anymore. I scanned for a single, worthy compliment in the craw of each day.

Tom Chiarella, you have written a wonderful piece. I hope others can learn from you.