17. The end of small talk

I’ve been on a handful of dates in the past month or so. While I enjoy going on dates, there’s something that’s been tiring me about them. It’s the resume of things we seem to discuss before we

get anywhere near a connection.

These revolve around many everyday things: job, commute, living situation, family, siblings, location of siblings, age of siblings, high school, inevitable story about high school. Sometimes it feels like it’s a holiday gathering of relatives that I only see once a year. The same story, every time.

One of my not-so-guilty pleasures is the New York Times’ “Modern Love” column. It’s a guest-written column where people write love stories. They can involve missed connections, personal awakenings, arduous long-distance relationships, meet-cutes,  guilt, trauma, or just plain goofy things. I love it. The editor, Daniel Jones, does a great job of finding stories that don’t always fit the stereotypical love story.

I read this week’s column, “The End of Small Talk” with great delight. The author, a male, was in a pretty much similar situation as I am: serial dating without any glowing prospects. He changes his style and starts digging deep right away with big-picture questions.

As I’ve grown older and more in tune with my journalistic self, I’ve realized that I enjoy asking the questions more than I enjoy answering them. I demurred over talking about myself because I always thought it was a good idea to show more curiosity and interest in your date than in yourself. I used to think of myself as enjoying the spotlight, but I really don’t think I do unless it’s under a very controlled circumstance where I have time to hash out the right message. (For instance, my column, a class presentation, or a wedding toast.)

And while I don’t mind asking those small questions about work, friends, family and the like, you begin to wonder if that information really matters right off the bat. Will it change my opinion of a person whether they work as a teacher or a software engineer? Or if their commute is 20 minutes as opposed to an hour? I don’t think whether they have three or two siblings will really be a deal breaker.

So, on whenever my next date will be, I’m going to dig deeper. Go big right away. Doesn’t it make more sense to get a bigger picture right away? It seems odd to wiggle around the mundane things of life before you end up in a spot where you find connections over those essential things in life.

One of my favorite questions to ask people is: What’s the dream? Everyone has a dream, whether it’s to own a house or create a new business or write a book. Dreaming is universal.

I hope this works. The last few dates I’ve been on have been fine and nice, but that’s really about it. And, full disclosure, I’m pretty bad at second dates. I like to think I have a read on how the other person is feeling, but I’ve been known to be wrong.

So, you might as well reach big because even if you fail miserably, you know you took a good risk.