There are two kinds of first dates: awkward ones, and ones where time flies and before you know it, you’ve been nestled in the corner of a bar for four full hours talking about anything and everything.
The difference between the two? Asking the right questions. And while dating experts agree that showing up at drinks, coffee, or dinner with a list of questions prepared feels way too stiff (it’s not a job interview, after all), questions are also an inevitable part of any first date. Here, find twenty queries for your first encounter that will help you get to know your date, discern your compatibility, and spark engaging conversation. If you need some advice on even getting to this stage, check out the 20 Best Dating App Opening Lines.
“How did you choose this place?”
If your potential mate picked the date spot, definitely begin here for a natural conversation starter. “This is a great question that is an opener for a conversation that can go down many roads,” explains Julienne Derichs, a licensed clinical professional counselor practicing in the Chicago area. For example: Is this your favorite restaurant? What’s your favorite food? Do you enjoy cooking? Do you hang out in this part of the city? What was the last great band you went to see? These are all follow up questions that can keep the dialogue going while you get to know each other. Another tip to keep in mind: “You want to ask open-ended questions that encourage full responses rather than short yes or no answers.” And don’t ignore his or her body language when they answer, either: Here’s how to Read Your Partner’s Mind with These 10 Body Language Tells.
“What’s the worst date you’ve ever been on?”
First dates can be weird, so an ice breaker like this can be a great way to cut the tension. “Everyone has a story of their worst date ever,” says Jodi J. De Luca, Ph.D., a licensed clinical psychologist practicing in Colorado. “Comparing dating war stories it’s fun and usually results in lots of laughs, thereby minimizing the awkwardness of a first date.”
“What did you do last weekend?”
The biggest thing you want to avoid on a first date is making it feel like an interrogation, and this question allows you to be casual and still get a feel for who your date is beyond what their dating profile (or the friend who set you up) tells you.
“If someone still parties a lot, seems to have too many plans (if you ask them about more weekends and seem to get the same response), or just spends most weekends working, it may be that they are not relationship ready,” says Stef Safran, matchmaker and founder of Stef and The City. “If you get a sense that they have a routine, but one that leaves room for flexibility and fun, then you may get insight that this person could be worth that second date.” And if you’re staring down a second date, don’t miss these 40 irresistible second date ideas.
“Do you like your job?”
If you don’t know what they do for a living, you don’t have to straight up ask them. Instead, give them a chance to talk about their job in more general terms.
“Inquiring about your date’s feelings about a job gives insight into that person’s passions, priorities, and values,” says Amy Morin, a psychotherapist and the author of the bestselling book 13 Things Mentally Strong People Don’t Do. “Does your date work at this particular job for the money? Do they find meaning and purpose in what they do? Are they motivated to go on and do other things, or are they content with what they have now? It’s a great way to open the door to conversation about future aspirations and the role income plays in a person’s life.”
“Do you have any pets?”
People love talking about their pets, but there’s actually more you can read into their answer than just whether they’re a cat or dog person.
“You are getting an idea of how your date feels about making commitments,” Derrichs explains. Similar questions could include: “Do you have any houseplants?” and “How long have you known your closest friend?” “If your date responds by saying, ‘I’ve known my best friend since kindergarten,’ or ‘I have a dog and a cat and an apartment full of plants,’ then you can be pretty secure that your date doesn’t have any major commitment issues.”
“Where did you grow up?”
“Ask your date an innocent question like where they spent their childhood to gain some insight in their upbringing and their family situation,” suggests Margaux Cassuto, relationship expert and founder of matchmaking service Three Matches. “Share your own story to encourage them to be forthcoming. Knowing what influenced their world views can often (but not always) help you determine what kind of person they are today and help you decide if you want to welcome them into your life.” And if your relationship flourishes, consider really spicing up your bedroom with one of these.
“What do you think of social media?”
“If you find out that they are very interested in selfies, Instagram, Facebook, Twitter, and other social media, it might make you think twice about how much you want to share with them,” Safran points out. “Social media can often be like an addiction, and if someone spends more time sharing on their social media (or on the flip side, refuses to share anything at all), you may learn more about what a relationship might be like with them. Most people don’t want to date people who overexpose their life, or who refuse to share.”
“What are your friends like?”
“While it can be good to know what type of relationship someone has with their family, their friends are 100 percent their choice,” Morin notes. “Knowing who they choose to surround themselves with will help you learn more about who they are as an individual. Do they like to be around high achievers? Do they mostly spend time with people who like to drink with them? Have they had the same friends since childhood? Getting to know a bit about their social circle will help you get to know them without asking 101 direct questions that may cause your date to feel like it’s an interrogation.”
“Are you a big family person?”
How much time someone spends with their relatives can tell you a lot about them and what your life might be like if you continue to date them. “Is this a person who is very family-oriented and heads home for every Memorial day, baptism, and bat mitzvah?” asks Justin Lioi, a men’s mental health and relationship expert. “If you value your downtime and don’t love family ‘obligations,’ you’re going to want to know what you’re getting into.”
“Can I kiss you?”
Only ask this if the date has gone well, of course, but research suggests that kissing plays an important role in how we choose our partners. Surveys indicated that both women and men (but especially women) use kissing as a way to test out and evaluate a potential partner. So if you can see yourself having a second encounter with your date, there’s no reason not to see if a romantic spark is there when you lock lips.
“What do you do for fun?”
Before you roll your eyes at this question for being boring and generic, hear us out. “How your date answers this question can reveal a great deal about whether they are well-rounded and enjoy many interests or are just focused on work,” Derrichs says. If they’re not sure what they do for fun or they say they don’t really have time to do anything outside of their job, they also might not have time for a relationship.
“Which dating apps do you use?”
It might feel like bad form to ask something like this, but it may provide helpful hints about what your date is really looking for. “Most single people are using apps nowadays, but if somebody isn’t, it can be a sign that they are not looking for a relationship,” says Isabel James, matchmaker and founder of Elite Dating Managers. “If they are using them, ask which ones they use. OkCupid and Match.com users are usually looking for something more serious than Tinder, Bumble, and Grindr users.”
“Do you want kids?
Worried the first date is too soon to ask this? “I don’t think so,” Lioi says. “This is just something so fundamental, so before any feelings start flying, you want to know if the person does (or doesn’t) intend on sharing their life with other people who will arguably becoming a greater priority than you.”
“What’s on your bucket list?”
“Hearing about someone’s future goals can give you an idea of how compatible you might be,” Morin says. Does their dream vacation sound like a nightmare to you? Does their sense of adventure rival yours? Will their career goals take them to the top? “Understanding things they hope to do down the road gives you a glimpse of that person’s hopes, dreams, and passions.”
“Are you looking for a relationship?”
“Don’t be afraid to ask if they are looking for a long-term relationship with the right person,” says Laney Zukerman, relationship coach and author. “So many people tip-toe around asking this. It’s important you know from the start that if the pieces of the puzzle fit, they are open to that.”
“Where was your last vacation?”
Whether you love travel or you’re a total homebody, this question is a must. “If someone is a workaholic or they just don’t enjoy planning vacations, you may learn something valuable,” Safran says. “This question doesn’t probe too much, but does give you an idea if you are dealing with someone that shares your view of leisure and travel.”
“Would you say you’re independent?”
“If you’re looking for someone who will center you, you’re going to want to know how much they value time with others and how much alone time they’ll need,” Lioi says. Plus, if you’re the kind of person who needs time on your own, it’s important to know before you get in too deep whether you’re dating someone who mostly likes to be around others.
“What did you major in?”
In some cases, this question can lead to a lively discussion of shared academic interests, but there’s also some data to support the idea that you’re significantly more likely to marry a person who majored in the same subject you did. And even if you didn’t study the exact same thing, marriages were also more likely to occur between people who studied in similar fields, like the humanities, science, or law. Of course, there’s no need to write someone off for having a different educational background, but this question could provide some helpful context beyond your date’s day job.
“How do you feel about surprises?”
“This answer you may be able to infer from how your date deals with things not going according to plan,” Lioi says. “Were they totally flustered that the bar you planned to go to was closed and you had to go somewhere else? Remember that this is a person you’re going to eventually get stuck in an airport with.”
“Are you up for a second date?”
If the first date is going well, it’s often easier to judge their real interest in a second one by simply asking in person. What’s more, you’ll probably learn a lot more about them on date number two, so even if you’re not totally sold, it’s worth giving it a chance.
“Second dates are a better gauge of compatibility because you have more information about each other,” De Luca says. “Second dates allow you to validate and or challenge any assumptions you may have had about the person on the first date. By doing so, you have more information to make a better decision, and not rush to judgment about whether or not this is an individual that you would like to see again.”
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