How to have a fun & fascinating conversation with anyone.

A few nights ago, I found myself on the backlot by Stage 14 at Paramount Studios, chit-chatting with entertainment execs over white wine and heirloom tomato salad with a balsamic reduction. Whilst wearing a reeeeally foxy red dress.

Now, I’m not in the “entertainment industry,” and I was there as an outsider — a curious voyeur.

And I couldn’t help but notice that all of the Hollywood Hottie McHotShots at my table were talking about work, work, work.

Will Smith blah-be-de-bloo, promotional cross-over-lah-bah-dee-bah, tightening overhead tra-la-la-la-la.

Don’t get me wrong — I love talking about my work, too. But that night, at that moment, I was craving a new conversation.

I noticed that the person seated next to me (let’s call them, “Quiet Person”) was awfully … quiet.

Quiet Person had arrived alone, without a date or colleague to hold their attention. Quiet Person was tapping away at their smartphone, detached from the room.

I could have turned to QP and said:

“Hi. I’m Alex. I’m a writer and entrepreneur. Nice dinner, huh? So, what do you do?”

Instead, I turned to QP and said:

“Hi. I’m Alex. What was the BEST part of your day?”

QP looked startled, then delighted, then contemplative. I saw QP’s wheels quickly spin, eyes brightening in reflection.

“Actually … now that I think about it … I had a really fantastic workout at the gym.”

We spent a few happy moments talking about how much we both love workin’ out … which flowed into a conversation about our favorite TV shows of the year (QP: REVENGE. Me: SCANDAL) … which swirled into a conversation about our shared love of classical music and opera (we swapped Wikipedia factoids about our favorite pop-crossover tenor, Andrea Bocelli).

Our careers briefly came into the flow of conversation, as they tend to do. But they weren’t the focus.

And yet, at the end of the night, QP handed over a business card, encouraging me to reach out to see how we might work and collaborate together. As it turns out, QP is the director of a major non-profit organization — one with considerable clout and prestige.

Who knew? (I didn’t.)

The happy lesson here?

If you want to have a fun, fascinating and opportunity-generating conversation, you don’t need a “strategy.”

You just need to ask a question that nobody else is asking.

What’s your go-to conversation starter?


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