When I was your age, it was nice old Jewish ladies who thought I was the cat’s meow. And, like you, I completely discounted it because I couldn’t get the correct age demographic to react the same way. But here’s the secret I’ve discovered way too late in life — networking. Every old guy who thinks you’re great may have a daughter or niece. Throw in some comment about your spacious brownstone feeling so empty and you should be on easy street.

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Ad agency creative director, writer & designer at https://guttmanshapiro.com. Former pro tennis player and peak performance coach for professional athletes.

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