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When it comes to dating, there’s plenty to discuss—bad behavior, horror stories, the list goes on and on. But there’s something a little more basic that isn’t as often discussed: what to actually say on the dates you go on.
After all, first dates often come with a ton of nerves. Our minds might spiral out of control: Will they like me? What should I wear? What if I make a total fool of myself? We’ve all been there before. It’s the worst. To ease some of the mild panic before it occurs, it’s a good idea to go prepared. With that in mind, we spoke to dating experts about what to talk about on a first date. Read on to find out more.
Start with the little things
The way we dress is a window into our character—and that’s especially true when it comes to accessories. It’s rare to accessorize with a piece you have zero story or sentiment around, so inquiring about a personal talisman often leads to some reveal. Perhaps their necklace was purchased on an amazing trip abroad (now you can talk about travel!) or it was a gift from a loved one (now you can talk about family!). Just keep in mind that soft phrasing is always helpful here; if it’s a religious or culturally significant piece, you want to proceed with gentle curiosity. “Can I ask about this?” is always an ideal way in.
For example, I wear a slew of gold signet rings, and on one date a guy asked me about each one. It led to five micro conversations around favorite stores, family heirlooms, aesthetic preferences, and so much more. Watching him solemnly nod along, head lowered and eyes fixed, was incredibly endearing. Letting him try some on felt like breaking through that first wall of formality; two adults at a bar became two kids playing dress-up.
Amy Van Doran, CEO of Modern Love Club, a luxury matchmaking agency in New York, says this is a great way to establish intimacy. People want to feel “seen and cared for by the date,” she notes. Curiosity about what a person holds close to their body is a seamless way to accomplish just that—in the most literal sense. It can also help facilitate respectful touch and an opportunity to get closer.
Ask open-ended questions
Asking open-ended questions is a method that’s employed by psychotherapists and journalists alike—and for good reason. Open-ended questions work because they can’t be answered with a simple “yes” or a “no.” Some classic examples are: What did that look like? What was that like for you? How did that make you feel? These types of loose prompts often allow for more interesting, honest, or vulnerable answers.
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 Doran 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 Doran. “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.
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.”
Nerves can sometimes be to blame when it comes to rapid-fire questioning. But asking questions—even follow-up questions—aren’t the only way to progress a conversation. Rephrasing or affirming can help the conversation along and make space for your date to go deeper on their own accord. Let’s say someone’s sharing how much they love cooking. You could ask them what they like to cook. Or, you could rephrase and say something like, “Wow, it sounds like you’re really the chef of your friend group.” Or, you could affirm by saying: “It’s cool how much time and effort you’ve dedicated to something completely outside your career.” Both options offer the opportunity for them to tell you more—and make them feel both understood and heard.
First date topics to avoid
First off, it’s important to keep it positive. “Don’t go too deep on exes, family trauma, or politics,” Van Doran advises. “Avoid negative talk about yourself or others. Even if you are in agreement, it doesn’t make for an emotionally uplifting experience. A first date is for seeking the spark between you, not for airing out grievances.” I recall one situation in particular in which my date spoke at length about his erratic, aggressive ex-girlfriend, turning our meetup into his own therapy session. At the end of our date, he kissed me and said, sadly, “I’m never going to see you again, am I?” He knew.
Questions with an ulterior motive are also not a good move. When a question is thinly veiled, most people aren’t fooled. Kai’s friends often complain to her that they can always tell when someone’s trying to figure out how much they make, “because they’ll sort of ask around the question or be like, ‘How much do you pay in rent?’” Asking such questions is “fraudulent,” she says. “If you're looking for a high earner, own it. But if you’re trying to mask it as something else, that’s disingenuous.” This disingenuousness is why she also advises against talk about politics or religion; she finds people often fall into using these topics as a platform to flex or to be contrarian rather than earnestly express their beliefs.
Hard-hitting topics aren’t off the table for Boodram; she says the key is to talk about them with authenticity. “Rather than waiting for the bill to come to judge the other person’s view on money, ask them what their parents did for a living, or even ask them about how they grew up thinking of money,” she suggests. “These kinds of questions signify that you’re genuinely trying to get to know someone, which should be the goal of a first date.”
How to avoid awkward silences
Silence can be powerful in bringing conversation to new territory. I find that giving an extra beat after someone is done speaking actually allows them to continue on in a deeper way. Just keep in mind how much body language can communicate. For example, when a date shares a particularly tender anecdote, it might be best to just quietly nod along. “Silences don’t have to be awkward. You can enjoy the pauses, and there is a power in allowing for spaces that give the conversation room to breathe,” says Van Duren.
You can also acknowledge the weirdness. “Have a sense of humor about how first dates can be awkward—nobody is completely themselves,” she notes. “All you need to know after a first date is if you are open to seeing the person again.”
A more common issue isn’t being at a loss for words, but being on a date with someone who's slacking. “There is a lot of onus on the woman to carry the conversation in a traditional male-female date,” states Kai. “I could just continuously ask you questions and tell you about myself without you asking me, to keep it going. But I would get to the end and feel like I just ran a freaking marathon.” Boodram’s tip for ensuring equal participation? “If there is silence because the other person is yet again waiting for you to ask them another question, softly nudge them: ‘Wow, I realize I’m the one who's been asking all of the questions. I have a habit of doing that when I’m interested in someone…’ They should hopefully get the hint after that.”