Whether your mind is speeding ahead after one great date or you’re on the cusp of getting serious with someone you’ve been seeing for a while, find your footing with these queries.

By Sarah J. Robbins
Updated February 08, 2017
Ben Wiseman


First be honest with yourself—then get on the same page with your new partner. There’s a fear of scaring people off with “big” questions, but those questions are important. Recently a woman wrote to me about a relationship she’d been in for two years; she had just learned that her boyfriend didn’t want to have kids. She’d never asked—and now, at 36, she’s wondering, Do I stay or do I go? Age can be an important factor. I’m 39, and if someone asks me on a first date whether I’m thinking of having children, that makes sense to me. We all have a list of things we want, but that list can change. If you find your relationship is bringing you joy but not matching your list, maybe it’s time to reassess the list.
—Meredith Goldstein writes the daily “Love Letters” column for The Boston Globe.


Don’t go into dates with an agenda. When you operate as some kind of sleuth (I have 90 minutes to figure out what this guy’s deal is), the questions, no matter how clever you think they are, are never subtle. A good date is like sitting next to someone on a plane—just a natural conversation. Be yourself and don’t stress too much about impressing or being impressed. Afterward, you can evaluate the experience. Ask yourself, Did I have fun? Was I attracted to him? Was I comfortable? Was I being myself? The answer to all those questions has to be yes. If it’s not, there’s no need to pursue the relationship.
—Evan Marc Katz is the author of Believe in Love: 7 Steps to Letting Go of the Past, Embracing the Present, and Dating with Confidence. He lives in Los Angeles.


There have been times in my life when my gut has screamed, He is not for you! and my head or my will has ignored that and said, Nope! I’m gonna do it! Deep down, we know when we’re seduced by the package but the substance we’re looking for is not there. I find that I get an honest answer when I do a gut check, the way I might ask myself, What do I feel like eating today? Partly it’s noticing whether this person brings out the best in you. I’ve dated people who made me want to be kind, generous, patient, and sweet. And I’ve dated others with whom I ended up gossiping for three hours about people we both knew. The latter can feel naughty and exciting, but ultimately it’s toxic. It’s also a sign that you probably don’t have much in common.
—Halley Feiffer appeared most recently on Broadway in The Front Page. Her own plays have been produced by Atlantic Theater Company and MCC Theater, among others. She lives in New York City.


There are hundreds of studies about how we rationalize things in our romantic relationships. One term for it is “positive illusion”—a halo effect that leads you to see an idealized version of your partner. A little shine is OK within reason, but like many things, it can go too far. Relationship researchers have found that family and friends actually do a better job of predicting whether a relationship will work out—and a better job of rating a partner’s individual characteristics, like kindness—than the other person in the relationship. In statistics, we say that it takes three data points to make a trend. So ask a diverse group, “What do you really think?” Then aggregate the answers.
—Ty Tashiro, PhD, is the author of Awkward: The Science of Why We’re Socially Awkward and Why That’s Awesome. He lives in New York City.


You don’t have to agree on everything, but take note of meaningful disparities—and how you two manage them. Say you’re on a walk and see a homeless person. If you feel compassion but your date says, “That guy needs to get a job,” you might think, Hmm. The real question is: Can you have a healthy dialogue about your points of view? Differences of opinion often come from experience and upbringing. For a relationship to work, you need to be able to express your viewpoint while being open to listening to an opposing one. If you can be peaceful about big topics, you can come to an agreement about loading the dishwasher.
—Rachel Macy Stafford is the author of Hands Free Mama and Only Love Today. She lives in the South.