Ever listen in awe to a singer who could riff with notes and chords (think Tony Bennett), or chortle when a comedian improvised lines (think Tim Conway) to make the shtick even funnier? The ability to riff in conversation can create instant connections in dating, in relationships, and even with strangers.

Think of conversational riffing as flirting without an agenda. One person offers a line. The other builds on it. The magic isn’t in the content of each line – it’s the back-and-forth, ever expanding rhythm that’s brilliant.  

Here’s an example of a dating text exchange I had after my almost 25-year marriage ended in divorce. As a newcomer to dating – I hadn’t been single since my early 30’s – I needed to engage with men in a brand-new way. What I learned was how to use curiosity and timing to become playfully attentive. It wasn’t so much about being clever as it was about listening and taking a chance on advancing the conversation.

He texted the first question: “How tall are you?”

“5’7ish. You?”

“I’m 6’3”,” he replied.

Here’s my riff: “Love tall men and their clothes!”

And here’s his: “I might have a lot of clothes.”

Now, we were off and running…

“Oh, gosh! I might have more than you. Take that back. I definitely have more than you. And let’s not talk about shoes,” I admitted.

“So, we have to get two extra bedrooms for our clothes and shoes!” he came right back.

Both of us were instantly amused and wanted more. It might have gone another way if I had responded to his answer of height with an expected pedantic: “Wow, you’re tall!”

The Return of Playfulness

By the time we reach mid-life, most of us are fluent conversationalists. We know how to express ourselves politely and perceptively. We can carry a discussion through a dinner party, ask thoughtful questions, and make sure everyone feels included. What we are less practiced at – mostly because life has trained it out of us – is play.

Riffing is conversation with a twinkle. It’s doing small talk RIGHT. According to the research of behavioral psychologists Erica Boothby and Maya Rossignac-Milon, “many of the strongest bonds come from riffing playfully.” They go on to explain that “collaborative riffs are surprisingly central to our mental wellbeing.” Don’t play it safe, they say. Go off script.

“It’s like being a kid again. Children skip the boring ‘getting to know’ phase and jump straight into pretend play.”

That’s what happened to Marcus and me. In our very first conversation, he leaped ahead to the need for two bedrooms for our clothes and shoes, and thus endless riffing possibilities beyond!

Riffing doesn’t require being funny. It simply requires being present in the moment.

If you say this doesn’t come naturally to you, I get it. We’ve all spent decades being practical, appropriate, and productive. Somewhere along the way, many of us replaced spontaneity with polish. But it’s spontaneity that makes conversation memorable. It’s noticing the comment beneath the comment and choosing to engage it.

Listen for the window of opportunity and follow it!

Take the Conversational Risk

Most of us have been taught that conversational openers should default to safe topics. And especially today, we are on heightened alert about what’s okay or not to say. We sometimes ask questions we already know the answers to. And predictably we exit conversations having learned nothing new and feeling no connection.

Riffing changes all of that if we take the risk of offering something unexpected. It’s noticing what someone just said and choosing not to let it fall to the floor.

“Be so good they can’t ignore you!” urges comedian Steve Martin.

You Are in Control of the Conversation

When I moved to New York City from Texas, I didn’t know the rules yet. I didn’t realize that silence was a kind of social contract. I talked to people everywhere because that’s what I had always done – and to my delight, it often worked. And that’s when I learned something important: the City wasn’t ever anti-connection. It’s anti-intrusion.

In dating, there’s a big difference!

Reclaiming social confidence during ‘later in life’ dating doesn’t mean abandoning discernment. It means still knowing the difference between curiosity and caution. Riffing isn’t about engaging without boundaries. A playful comment doesn’t require follow-through If you don’t want it to go beyond where it started.

But I urge you to take a chance. Getting good at engaging has paid off for me, and I hope will do the same for you. After all, riffing is one of the fastest ways humans can deeply connect. I’d love to hear about your experiences at Kate@KateSomerset.com.