First dates can be a lot of fun, but they can also be incredibly nerve-racking — especially if you are getting back into the dating scene or are generally shy when it comes to meeting new people. This can make asking good first date questions challenging, never mind navigating those dreaded awkward silences. Luckily, these dating expert-approved ideas for questions to ask on a date will help make your first meeting go as smoothly as possible, so you can focus on having fun and getting to know the person in front of you.
Woman's Day spoke to relationship experts including matchmakers, dating coaches, psychologists, and authors to find out the best questions to ask on a first date that’ll help you decide if there should be a second. The first date should be about testing the waters and asking mostly surface-level questions. Matchmaker and dating coach Stefanie Safran suggests that you come to the (literal or metaphorical) table with a few questions in mind. She adds that if you ask a more sensitive question, it's important to note their body language, and put a cap on this line of discussion as things could become uncomfortable. Just like there are flirty and romantic questions to ask on your first date, there are also some "juicy" questions you should probably avoid.
The bottom line, as Darma dating app founder and dating expert Meredith Golden notes, is that "the first meeting isn’t used to decide if this is your forever person, and the topics discussed during this first meeting should reflect this. If someone is a hard no, this will be obvious. If you had fun, this too will be clear." Dating is already difficult enough, so let these more lighthearted questions guide the conversation on a first date.
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Questions to Ask on a First Date
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How are you?
"A successful first date is going to require two people who are both present for an evolving, unfolding, and curious conversation, versus a series of questions that feels more like an interview than the first chapter of a love story," says Dr. Alexandra Solomon, licensed clinical psychologist, professor at Northwestern University, and author of Loving Bravely. "The question, 'how are you doing these days?' is hopefully enough to start a conversation that you could get lost in." Although basic, sometimes an open-ended question can lead to the best conversations.
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What brings you joy?
"The healthiest relationships are the ones made up of two people who know how to stoke their own fires. They can cultivate happiness, wonder, and gratitude in their own lives," says Dr. Solomon. "You want to see if the other person talks about things they’re passionate and enthusiastic about. A red flag would be someone who laughs at the question or holds it in contempt. If you’re someone who is genuinely curious about what makes people tick, and the person sitting across the table from you thinks a question like this is ridiculous, it could be an indicator that you may not vibe well together." After all, a first date is meant to help you determine if you want there to be a second.
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How do you like to spend your free time?
"This gives your date a chance to share with you what some of their interests, passions, pursuits and pleasures are," says relationship and wellbeing coach Shula Melamed, MA MPH, NBHWC. This question is also a great way to learn what you and your date may have in common.
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What do you want to do now that the world is opening up?
There is a lot of ground to cover when it comes to discussing what the both of you have probably missed experiencing over the past two years. Safran points out that it may be a good idea to at least briefly touch on the pandemic: "Put a little out there about COVID-19, because some people might be uncomfortable about kissing during the pandemic." Obviously, you don't have to kiss on the first date, but it is good to know where you both stand regarding social distancing, and asking a more lighthearted question to get into that topic can make it a lot less daunting.
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Who are you hoping to see in concert?
This is an easy and fun question to ask on a first date, recommends Golden, especially if they have already indicated they like live music.
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What's your job?
If their online dating profile includes their job position, you could also ask for them to elaborate on their work. Questions like these are "effective on a first date because they break the ice, yet they are not too heavy," explains Karenna Alexander, certified matchmaker and author of A Woman's Guide to Understanding Men: Dating Secrets Most Women Don't Know.
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What's the best book you've read recently?
"If you’re worried that conversation might be strained, the conversation can always be shaped around favorite books, podcasts, music or food," says Golden. She adds that "even if they don’t have a good answer, most people will reciprocate the question." Soon enough you will have a conversation flowing between the two of you, while also learning more about their likes and dislikes.
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What movies have you seen lately?
"I think daters should be 'light and breezy' on a first date," says Alexander. "Usually, a first date is just a way to see if there is chemistry. It shouldn't be too deep, which is why I believe questions should not be deep. You never want a first date to feel like it's turning into a therapy session." So, focus on some favorite movies you may have in common. And if one or both of you hasn't seen anything new recently? Well then you might just have a perfect second date idea.
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What's the best meal you've had this year?
Golden recommends using "the first date to see if you have fun, feel comfortable (as much as one can during a first date), laugh, and have easy conversation." And reminiscing about a delicious meal is an easy way to loosen up anxious nerves.
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What's on your bucket list?
"It can be awkward to ask someone what they're looking for romantically," says dating coach Hayley Quinn. That's why she recommends asking this (much more fun) question instead. "If you're looking to settle down, and they want to travel to Peru, you may not be a match. If there's a big mismatch in life goals it's good to find this out earlier rather than later," she adds. By leading with this question you can better understand your compatibility in a more discursive manner that doesn't put them on the spot, explains Quinn.
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What do you want out of life?
This is another way to phrase the "What are you looking for?" question, without explicitly asking it on the first date if that feels like too much for you in the moment. Asia Dawn Simonelli, a relationship coach with a holistic coaching certification from Integrative Wellness Academy, describes the hallmarks of a deeper question such as this one: "When you know this from the first date, you won’t waste your time going on a second or third." While this can be a trickier question to navigate on a first date, it's important to get an idea of where the other person sees themself down the line. "Own who you are, and be yourself. Be unapologetic about what you’re looking for," says Simonelli.
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What's your idea of a perfect day?
"This can help you understand what the other person enjoys doing for fun," says relationship therapist Jaime Bronstein, LCSW. "What do they like doing when they’re not working, and would you want to be part of that?"
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If we met 10 years ago, or 10 years in the future, do you think we would have clicked?
Quinn reminds us that asking each other questions is also a great way to flirt during the date. "This [question] gives you both an opportunity to talk about if you're attracted to each other, and flirt, in a subtle way. If you're attracted to someone then it's good to indicate this on your first date, to help create some spark, and make the other person more excited to see you again."
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What's your relationship like with your parents?
"What this question is really asking is: What have you seen of love? It will give you a lot of information," Bronstein explains. "Of course, keep in mind that people who didn’t or don’t have a good relationship with their parents can still heal and be wonderful partners." Melamed adds, "Interrogation can make conversation awkward, forced and uncomfortable," so tread carefully as you delve into deeper topics.
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Are you still close with childhood friends?
"This question gives you information about their ability to have long-term relationships," Bronstein says. "Do they keep in touch with people? Are they able to maintain friends for a lengthy amount of time? You want someone who has their own friends and their own life, who isn't a chameleon, blending into their significant other's life."
What NOT to Ask on a First Date
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Why are you single?
Safran explains that asking a question similar to, "You are so pretty. Why are you single?" isn't a compliment. Talking about their single life may bring up previous relationships, which can be a murky topic of discussion that you want to approach with sensitivity on the first date. Especially if the other person has gone through a difficult breakup, painful divorce, or has lost their partner. If, however, a question like this does come up, Quinn suggests reframing your answers by focusing on what you learned from this past relationship. "Perhaps a divorce gave you clarity about what you really needed to be happy in a relationship. Even in the case of bereavement, you can tell someone how that relationship was meaningful to you, and how that's shaped what you're looking for in the future."
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How long have you been using X app/service?
If you are using one or more dating apps to meet people, then steer clear of asking this question on a first date. You probably wouldn't want to be asked this question yourself!
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Do you want children?
This is a notorious no-no — in most situations. When interviewing men for her book, A Woman's Guide to Understanding Men: Dating Secrets Most Women Don't Know, Alexander found that this question "implies to them that you are asking them if they will have children with you. It scares them off." Safran adds that you could lead into the "kid question" if the situation feels right, but still be aware that this topic can be sensitive.
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Do you think your parents will like me?
This is also a no. "It's too much too soon. I know people who have been asked this question, and every single person has said it has made them very uncomfortable," says Alexander. Meeting each other's parents usually happens down the line in a relationship, so asking about this on the first date is jumping far ahead when it's more important to focus on determining whether or not you are enjoying yourself now.
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What are you looking for?
"People ask this often, and it’s pointless! Dating isn’t ordering [from] a wishlist on Amazon. All the boxes don’t need to be checked," Golden stresses. You could think they are your perfect match and then find out that the opposite is actually true.
On the other hand, Simonelli points out the potential merit in asking this question: "You want to find out right away if this person is aligned with your lifestyle and values."
At the end of the day, Golden says, "You never know. Don’t create limitations by asking this — be open." And that is probably the most important advice about dating: Be open to possibility, as meeting someone can happen at the moment you least expect it.
Elizabeth Berry
Editorial Assistant
Elizabeth Berry (she/her) is the digital editorial assistant for Woman’s Day, where she covers seasonal recipes, holiday gift ideas, and other lifestyle topics for the website.
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