The craze over the 36 Questions posited by the New York Times last year as the pathway to falling in love with someone would draw skepticism from any true love cynic. The thinking behind the questions—ranging from mild to moderately-probing questions about life and death and relationships—is that opening up to someone about these topics introduces vulnerability and openness, and mutual vulnerability inspires intimacy (yada, yada, yada). But everyone knows that a vulnerability session is not always a comfortable way to while away the hours when you’re getting to know someone.
To get a second opinion on what types of questions people could ask someone they’re dating to get to know them beyond the surface-level, we spoke with Dr. Monica O’Neal, a clinical psychologist and relationship expert based in Boston who lectures at the Harvard Medical School.
She notes that there is no cut-and-dried “correct” way to approach dating and getting to know someone, nor a specific set of questions everyone should ask a partner, but she advises people—especially those looking for more serious relationships—to think about questions that help you have a better understanding of what you need and whether or not somebody is a good fit for you—intellectually and emotionally.
“YOU WANT TO MEET SOMEONE WHO’S WILLING TO SIT THROUGH THE DISCOMFORT AND THE AMBIGUITY AND TO BE ABLE TO ASK DEEPER QUESTIONS AND BE CURIOUS ABOUT THE RESPONSES.”
“If you think about it,” she says, “if you’re dating someone, and you’re going to eventually want something serious with them, you want to meet someone who’s willing to sit through the discomfort and the ambiguity and to be able to ask deeper questions—not get fixated on whether something’s right or wrong—and be curious about the responses.”
Below, her recommended questions for a typical dating sequence, from the first date to a point where you’re getting more serious about someone. Timing of these is important, she says, based on what age you are, where you’re at in a relationship, and whether you’re pursuing a more serious relationship or not. Yes, the questions are a little scary, but the goal is to ultimately gauge a response that helps you read whether your partner demonstrates a range of valued traits, from openness and flexibility, to curiosity and empathy.
“What made you decide to swipe right? What made you decide to ask me out?”
Dr. Monica O’Neal: I would say that this is a good question for everybody to ask, regardless of their age range, not in a way where you’re questioning, “Why do you like me?” but more along the lines of, “What about me in particular made me stand out?” I know some people might think it sounds conceited, but I don’t because I think it gives a nice opportunity for the other person to volley and say, “What made *you* decide to do it?” How deep or how thoughtful the other person is might give you some information about who they are. If they say, “Well, you’re hot or you have nice boobs,” that might be true and it would be rude if they said they didn’t find you attractive, but you want to know that they’re going to go deeper than your physical qualities. And on the flip side, be honest with them and see how they respond. And if they don’t respond at all, people might say, “I don’t know, it’s too deep of a question.” You have to ask yourself, “Do you want to be with somebody who would be that quick to shut down? Or do you want to be with someone who has a little more room to push themselves and go someplace different?”
“Have you been in love before? What kind of person do you typically fall for?”
MO: There’s magic in this question. I usually suggest this for a slightly older crowd, and this is a question that you have to pull off with a lot of confidence. You can ask this in the context of knowing what made the other person swipe right. And really listen, pay attention, have a little conversation about it. And then when they quiet off a little bit, look them solid in the eye and say to them, “Do I seem like I’m that kind of woman?” It’s a very powerful moment. What it does is, you can see the other person get uncomfortable. And it’s not like you’re trying to make them uncomfortable, but you want to stop the music for a moment and make sure that they’re looking at you in a particular way. And the people who can do that and want to do that, I think that would give you a real clue if this is someone to pursue. And that’s a subtle way of saying, “I want something serious. I want to be special.” Because we all do.
MO: I would say that this a third date type of question. It doesn’t have to be as straightforward as, “Tell me about your last relationship.” It can simply be like, “Oh you’ve been in a relationship. Well, tell me about it. How’d you meet? How did it end?” And so on. You don’t want to go into too much detail but I would listen to see if you hear, “Oh, it was mutual.” I think that’s BS. It’s never mutual. Somebody has to pull the trigger, even if both people are unhappy. I would really listen to how somebody answers that question. Are they answering that question openly and honestly? Are they putting down their partners?
“Of all your past exes and people you’ve dated, what is the thing they complain the most about you?“
MO: This is for when you’re really liking each other, maybe on about the fourth or fifth or sixth date. And pay attention if someone says, “They wouldn’t say anything. I was a great boyfriend.” And be prepared to give your own answer. At any point during the first few four or five dates, you shouldn’t be disclosing the most painful baggage. Be careful about the stuff that you share about family. You don’t want to go too fast, too deeply, because it’s hard and vulnerable. And you should only make yourself more vulnerable when somebody’s proven that they’re someone you can go a little deeper with.