“I’m Really Shy And Introverted. How Do I Date?”

Dear Cindy,

I’m really shy and introverted. I’ve been living in New York for the past three years and I’ve only been on two dates. What do I do about dating?

I was asked this question IRL a few weeks back in an informal setting where there were a number of other people, all of whom ended up hanging on my every word as I responded. This was clearly a popular topic, so I thought I’d share my responses for Dear Cindy.

It’s worth mentioning that this question was asked by an extremely attractive young woman - which I reference because this was not someone anyone would have thought, on looking at her, would have had any trouble dating.

I recommended three things.

The first one may surprise those of you who already know that I call myself one of the biggest ambassadors for online dating…..