My wife Jennifer is one of those naturally outgoing people who can quickly and easily strike up a conversation with a stranger. Back in the days when we would pull up at a toll booth and actually hand money to a human being, I was consistently amazed at how Jennifer would make a friendly connection with the toll collector in the time it took him or her to make change. In those few seconds, the toll collector would brighten up, chuckle, nod at something my wife had said, and sometimes toss back a response as if the two of them were old friends connecting across a backyard fence.
By contrast, I’m a bit introverted. I always feel a little awkward meeting new people and I’m especially ill at ease at large gatherings of full people I don’t know. (Granted, that won’t be an issue for a while, courtesy of Covid-19.) My self-consciousness has led me to look for conversation starters — questions I can ask that are reliable for getting a conversation going.
I read a Town & Country magazine article years ago that contained tips from an array of socially active people for how to start conversations at a cocktail party. (I would link to it but it’s apparently no longer available online.) Some of the suggestions seemed like something you might ask at some point in a conversation but not necessarily at the outset, like “If you could have an alternate career, what it would be?” Other questions seemed too presumptuous or just plain weird, like “What do you consider to be the driving force in your life?”
The conversation starter I keep coming back to is “What’s making your life interesting these days?” There’s a subtle compliment in that question, in that it assumes that the other person’s life is interesting in some way, but more important, it doesn’t limit what aspect of their life they can tell me about. I’ve had people tell me that what’s making their life interesting is a big project at work, and others that it’s baby-sitting their grandchildren.
Whatever they say usually provides enough grist for the conversational mill to keep it turning for a while. If it starts to falter, I’ll often ask whether they have any travel plans in the works, which can then roll into a question about where in the world they’ve most enjoyed visiting.
Perhaps the most important lesson I’ve learned is that nothing works better for having an engaging and worthwhile conversation than being interested in learning something from the other person. “What does a typical day look like for you?” could be a gimmick for getting someone talking, or it could be an honest expression of an interest in learning something I didn’t know about the type of work this person does. I’ve shifted from thinking of these kinds of conversations as “small talk” to thinking of them as “conversations for learning.” When I go into a social situation thinking, “I’m going to learn something new from everyone I talk to today,” everything goes much better than when I assume I need to “schmooze.”