You could spend the hours before a date obsessing over your hair, makeup, or outfit. Or you could channel that energy into brainstorming what to ask the stranger you’re splitting a basket of breadsticks with to figure out if you might want to eat dinner together forever.
“There’s so much disappointment in dating today, and one of my goals is to empower people to remember how much of their dating life is in their control,” says Damona Hoffman, a celebrity dating coach, host of the podcast Dates & Mates, and official love expert of The Drew Barrymore Show. “It’s really important that you express yourself clearly and get to know the person across from you, so you have the best chance of having that relationship continue or identifying if it’s not a match.”
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We asked Hoffman and a Love Is Blind success story exactly what questions to ask on a date—plus what they might reveal.
“What’s the last concert you went to? What about the first?”
Prioritize questions that encourage your date to tell a story, Hoffman advises. Instead of asking what kind of music they like, for example—“oh, you know, a little bit of everything”—tap into their sense of nostalgia by asking them about the first concert they ever attended, as well as the most recent. “It gives you a sense of not just who that person is sitting across from you, but what they connect to emotionally,” she says. Plus, sharing fond memories can promote a bonded feeling.
“I gotta know: Are you a morning person or a night owl?”
This-or-that questions tend to work well, Hoffman says—like asking your date if they prefer rising early or staying up late. “I’m a morning person for life, like diehard,” she says, which means if someone asked her this question, she would answer enthusiastically. It would inspire her to start talking about her morning routine and love of the sun.
If her date told her they were a night owl, she’d dig in further, asking what they did with all those hours, which can lead to a conversation about how they both liked to spend their time. By the way: It’s not necessarily a deal-breaker if you’re partial to different schedules. Hoffman married a night owl.
“What’s your relationship goal?”
If you’re looking for a long-term commitment, and your date is in their situationship era, it’s best to find out as early as possible. Yet people are often afraid to broach the subject, Hoffman says, because they dread being disappointed once again or don’t want to scare off this person who had seemed so promising. She advises asking anyway. “The clearer your question, the clearer your answer,” Hoffman says. “People will tell you who they are the first time.”
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“What excites you about your work?”
You already know how tired it is to ask someone what they do. Yet it’s also a helpful thing to learn. A better way in, Hoffman says, is to ask them about their work goals or what they’re building or currently excited about. ”I wouldn’t want anyone to get into a long discussion about work on a first date, because that’s not your purpose there,” she says. Instead, use this entrypoint to spark a conversation about what energizes them and what they’re passionate about.
“Who are you closest to in your family?”
The key to this question is not judging your date’s response. “Their relationship with their family does not define their relationship with you,” Hoffman says. “I hear from daters who are like, ‘Well, I come from a really close family, so the person I’m with must have a close relationship with their family, too.’ I think that robs the other person of the opportunity to have done their own work and become their own person.”
Still, the way someone answers this question can be revealing, she adds, and give you a sense of what you might expect if the relationship progresses. (A huge, Hallmark-esque Christmas, or escaping to a tropical island far, far away?)
“Tell me about your best friend.”
Taylor Krause met her husband, Garrett Josemans, on season 7 of the Netflix reality show Love Is Blind—which means she got to know him through a wall, going on dates in small isolation rooms in which she could hear his voice but not see him. The couple, who got engaged before laying eyes on each other, celebrated their one-year wedding anniversary in November.
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Asking her future husband smart questions was “everything,” Krause says. She recalls prioritizing intentional questions that would reveal important insights, either through the answers themselves or the waythey were answered. Take the matter of someone’s best friend, which Krause prefers to explicitly asking about family. “Your friends are the family you choose, and I think it tells you a bit more about the people your potential partner surrounds himself with,” she says. “It should be a fun topic—and if it’s not, then maybe that tells you something, too.”
“What makes you feel alive—and what’s on your bucket list?”
Taking a spin through each other’s bucket lists can help you and your date figure out what a future together might look like—and how compatible your interests are. “It gives you an idea of how your person wants to spend their life in its most fulfilling moments,” Krause says. “It’s a good, fun, easy question that tells you a bit more than just the surface-level information.” Her husband, for example, is an avid spearfisherman, while Krause loves traveling. The two quickly figured out that their interests would be a natural fit to enjoy together.
“Who’s your role model, and why?”
This question will give you a sense of who your partner aspires to be like. “A lot of the time, it could be a parent, and we know that your environment and your upbringing really informs who you are as an individual and how you’ll act in the future,” Krause says. Or if they tell you they look up to that washed-up movie star with a criminal record and more significant others than recent roles? Well, that’s good to know, too.
“Do you want kids?”
This is a big one—and there’s no reason to delay asking a date where they stand. Krause has been surprised to discover that many people she knows don’t talk about whether they want to have kids before they get married. Then, it turns out “they’ve maybe made some assumptions about what the other person wants, or their willingness to change their mind,” she says. “Maybe you don’t have to decide right then, but it does give you an idea of the trajectory of where it could go and the desires of your partner.”
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“What’s your dream lifestyle?”
Few people relish having the money conversation—it’s an awkward thing to discuss. Yet it’s essential for couples to be on the same page. “It’s just the reality that money allows us a certain lifestyle, and it’s completely OK if there’s some people that aspire to live a certain way,” Krause says. “But that might require them to work 14 hours a day.” Maybe that’s no big deal to you; perhaps it’s a deal-breaker. Either way, it’s good to discuss openly.
“What are your thoughts on [insert value here]?”
If you and your partner aren’t on the same page about the values you hold closest, the relationship probably isn’t going to work. Krause suggests finding out in an open-ended way. For example: “What are your thoughts on feminism?” works better than “Are you a feminist?” (Switch it up with whatever other type of equity is most important to you.)
“Let someone tell you and show you exactly how they feel about the topic,” she says. “If they get really defensive, that’s probably telling. Being able to be upfront with your morals and who you are as a person is important, because it’s not going to work if you’re hiding those parts of you.” Plus, she adds, values aren’t something you should compromise on: “Don’t waste your time if you’re not aligned there.”
Wondering what to say in a tricky social situation? Email timetotalk@time.com