Why can’t you find someone interesting to talk to?
You’ve gone on a handful of dates and found each of them stunningly boring. “What’s the matter with people these days?” You wonder. It only takes another handful of dates to realize that perhaps it’s not them. The common denominator here is you.
How can this be? You picked the perfect spot for conversation. You asked plenty of questions and did your best not to talk about yourself unless they asked first. You only checked your phone once… are you boring?
Honestly? Yes. But if you find a person as boring as you are, you’ll probably find each other pretty interesting. You don’t have to be a world traveler to be interesting. You just have to admit you like doing puzzles on the weekends so you can meet someone else who likes that too.
The problem with a boring conversation isn’t that the person is boring, it’s that your questions are. Asking a bunch of broad questions and waiting for something to stick is just as good as not talking at all. The trick is to ask pointed questions, that direct your date to a specific time period, subject, or task. So let’s play a little game: Ask this, not that.
Ask the right questions
The first date
You’ve chatted a little bit through text but haven’t covered much. After a brief hug, she sits next to you at the table. You ask, “So, how’s it going?” Wrong. This is too broad and forces her to search for a topic. Instead, try “How’s your day been?” Simple, right? Keep it limited to today, or this week. This gives your date an opportunity to think of an interesting thing they did at some point in the recent past. Even if she simply runs through a list of things she did that day, you’ll learn a little about her and have a chance to pick something to talk about.
The second date
Today, you’ve agreed to grab coffees and go on a walk. You’ll have plenty of time to get to know each other. After your initial greeting, there’s a lull. You blurt out, “So, what kind of music do you listen to?” Wrong. At first glance, this seems like a perfectly acceptable question. Fine. You can have a perfectly acceptable answer in return. “Anything but country,” she says. Now you’re back to square one, with only a tiny shred of negative information. Instead, try “So, what was the last album you really liked?” This question is pointed. Your date won’t have to rack her brain for every song she’s ever heard to try and come up with an answer. You’ve placed a time constraint on the search engine. Oh, she really liked the last Childish Gambino one? Does she like the show Atlanta? How does she feel about his other work? Ride this new train of questions out for as long as you can.
The third date
Now you’re really getting to know each other. You figure it’s time to see if your political and religious views align. Stakes are high. This could end in a yelling match and you picked a very nice restaurant you’d like to come back to. You figure it’s best to keep it broad so you don’t offend her. You ask, “What are your political views?” She struggles for a moment, now afraid to offend you. Wrong. You haven’t relieved the pressure, you’ve only transferred it to her. Instead, ask about a recent article you or she has read. Talk about that topic, and use it to dig back into other topics until you get comfortable enough to talk about your opinions more broadly. Try to be understanding and willing to share as much as you ask for.
Worry about personhood
What do I mean by that? I mean ask questions that give you a chance to get to know what makes your date tick. Don’t be afraid to challenge their beliefs a little, or disagree. Offer recommendations of things you like that seem to suit their personality. It’s okay to talk about things that make you sad, or things you wish were different without complaining. Try to connect the things that make you two human, rather than trying to seem cool (or even just normal). And ease into it. Start with smaller conversations, and use those as hints into their personality. Then you can ask more probing questions without it seeming unsolicited or accusatory.
Sometimes, even when you try your darndest to get to know someone, it doesn’t work out. That’s okay. Thank them for their time, honesty, and good conversation. If it does work out, great! Keep getting to know each other. People are more complex than their music tastes and political alignments. People are dynamic and ever-changing. Never stop asking your partner questions about what they think or how they feel.