Taking it a step further, it’s also great to imbue open-ended questions with a sense of play. Questions like: What are you excited about right now? or Who’s your best friend? have a disarming earnestness to them. They’re the kinds of questions that make people smile. Van Doren agrees: “Date to create a fun experience,” she advises. “Be playful and explore topics that make your date visibly more energetic and joyful.”
To that end, you can also try gamified prompts, a la Vogue’s 73 Questions series. I love asking people for their “rose, bud, thorn,” where the “rose” was the best part of their day, the “thorn” was the worst, and the “bud” is what they’re most looking forward to. It lends the conversation a cheeky, conspiratorial feel.
In fact, bringing the entire dialogue into fantasyland is a nice way to reduce pressure while also offering insight into what drives someone. Ask your date about their perfect day—beginning to end—if time and money were not obstacles. Like, starting the day with a morning swim on a beach in Mexico, lunch at a little restaurant in Milan, dinner atop a cliff in … you get the picture. “Ask questions that activate and inspire the imagination,” says Van Doren. “If you can ask novel questions that a person hasn’t been asked over and over again, they’ll notice!”
Let the liquor speak
It’s no secret that many first dates take place in a bar. Take advantage of the setting and discuss drinking cultures. Every city and country has their own rituals, lore, ways to toast, types of alcohol, and more. Having a few to share is an easy party trick, something I’ve always found sparks interest on a first date. One favorite: in some Chinese cultures, it’s polite to clink your glass rim below the other person’s glass rim to show respect or acknowledge authority. In booze-filled celebrations like weddings, it can become a bit of a game —fighting to go lower until you’re basically on the floor. Drinking cultures as a topic can be a fun segue into talking about travel or time spent abroad, as well as cultural influence at large.
Seek knowledge with curiosity
“My favorite topic on a first date is one that they know a lot about and I am personally interested in. Everyone loves talking about themselves or their hobbies, and even if I don’t feel sparks, the date is never a waste of time because I learn something,” shares sex and relationships educator Shan Boodram. It’s a kill-two-birds-with-one-stone approach: you telegraph authentic curiosity to your date while also gaining free expertise. The other benefit? “It always made my date more open to answer personal questions about their past that I’d be inclined to ask if I thought there was a possible future to explore,” Boodram adds.
Video: Getty Images
Rephrase and affirm
There’s an art to asking questions, and there’s a real difference between those that dig deeper versus those lifted off a checklist. Dating influencer Anna Kai bemoans questions for the sake of questions, which can sometimes come across as a self-satisfied charade of inquisitiveness. “I went on a date with a guy and as he got drunker, he kept saying various iterations of the same thing: ‘Okay, so tell me, what are the four most important things in your life right now?’ Then he’d be like ‘Okay, so tell me, what’s really on your mind right now?’ and I just thought, I’m literally telling you what’s on my mind, and you’re not listening.”
