15 Questions We Should Actually Be Asking On A First Date—And 5 We Should Completely Avoid

We all know that dating is hard work. We women get all dressed up, apply special makeup, wear our favorite perfume and those horrible high heeled shoes that pinch our feet and make walking hard, and then we go out to a restaurant to meet a total stranger in the hopes of finding someone special. The men get all cleaned up, dressed up and prepared to plan a nice evening out and buy us dinner with the same hopeful outlook of finding someone special. There are different categories of dating—casual dating, speed dating, serial dating. But ultimately, we use dating to find our special someone, even if we must weed through several less special people till we find them.

One of the challenges with first dates is to overcome awkwardness and make a good impression. This applies to everything, including conversation. If we’re not that conversationally gifted, then this will be the biggest hurdle for us to conquer in our pursuit of true love. Googling lists and topics to talk about is one way to go but knowing which questions are important to ask, which are just conversational pieces and which should be avoided like the plague is a whole different matter and that is where the conversational skill comes into play. To help make things a bit easier for us, here is a simple list of 15 things to ask on a date and five questions to avoid.

20 Ask Away: Do You Read Reviews Or Follow Your Gut?

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Seemingly an odd question to ask but it can give a lot of insight into how your date thinks and makes decisions, however trivial. According to eHarmony,

“Seems like a strange one, but this helps you understand differences and similarities in a simple query.”

Some people will read lots of reviews before going to see a movie or read a book or buy something they’ve been eying online for a while now. Others will look at the book cover or the color of the car or who is starring in the movie and jump right in.

The one who reads all the reviews and carefully considers their options before buying is someone who will take their time before deciding if we’re the one for them or not. They’re cautious and like to know what they are getting into before investing too much time, energy and money. Meanwhile, we have the other side of the coin who thrive on risks, adventure and the unknown. They jump right into everything and go along with the ride till they’ve had enough, or their gut tells them the ride is going to end badly. They can be a riot to have around but also be a bit hard to pin down sometimes.

19 Ask Away: What Is Your Dream?

Everyone has a dream, or several tucked up their sleeves. Some involve future careers, others involve children or a nice house with a music room. According to eHarmony, “At any stage of life, dreams should be nurtured, cultivated, and acted on. Hopefully, you have dreams for your future, whether they involve career achievement, world travel, volunteerism or artistic expression. You want to know if the other person’s dreams mesh with your own. Listen closely to discern if your dreams are compatible and complementary.”

If our date has similar dreams to ours, this proves favorable for future compatibility should we decide to take this budding relationship out for a long haul. But if our dreams wildly clash, it’s best to know now rather than later when we’re more emotionally invested. Plus, it gives us something interesting to talk about over the appetizers which is always nice. People’s dreams are like their passions; they keep them close but once they get going talking about them, they become enthusiastic and excited. Occasionally we’ll run across someone who doesn’t have a dream and this conversation can get them thinking about it, wondering what their dream might be.

18 Ask Away: What Was The Worst Date You’ve Ever Been On?

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Definitely, an odd thing to ask on a first date but if things are going well and we’re relaxing over drinks enjoying each other's company, it can be a nice bonding moment. According to Huffington Post, “Only ask this question if you sense that things are going well, as their answer will reveal whether they can let their guard down and tell an entertaining story..."

"...Plus, it’s a great way to build an instant ‘us vs. them’ bond, as it requires the person to subconsciously reflect on how well your date is going compared to the one they’re recounting.”

Nothing quite bonds people together like shared horror stories of past experiences. Besides, if we can get them to mentally compare the two dating sessions and have ours come out on top, that’s a point in our favor and will go a long way to building something special with this person. And it will give us an edge in planning future dates because now we’ll have a better idea of what they won’t like, whether that’s surprises, swimming or sushi, it’s all data to be saved and stored for future use. Assuming we want a second date with this person of course.

17 Avoid It: What Are You Like In An Intimate Setting?

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This is an obviously loaded question and can take different forms of orientation and other personal preferences that could impact our long-term relationship with this person. Admittedly this is something we’ll want to know about our date at some point, but not on the first date and not till we’re comfortable enough to have this type of conversation. According to New York Times, “A study of 2,000 US adults found the ‘three-date rule’ could be a thing of the past. Results showed the average person polled would wait until date eight in an ideal world before taking things to the next step.”

Waiting to sleep together helps to build intimacy and avoid any awkwardness at the start of the relationship. It also saves us a lot of time wasted on someone who turned out to be too weird for us down the road. There are some of us who want to go to the last step on the first date which is perfectly fine, but we still don’t outright ask such touchy questions. We sneak around with indirect questions or feel out the situation and our date then go from there.

16 Ask Away: What Are Your Pet Peeves In A Partner?

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With just a hint at making this into a long-term thing, this question can save us all some time and effort in the long run. According to Huffington Post, “On a first date, we all put our best foot forward, but this question can cut through the facade and invite them to give an authentic response. They don’t like messiness and you’re a slob? We may have a problem. They despise country music, do you? Still in the running.”

Finding out what we have in common and what will likely tick us off as our potential relationship develops is something we are going to have to find out anyway, so might as well get a jump on it before we’re too invested in the relationship.

Pairing up neat freaks with messy people is a classic example of how opposites attract and then destroy each other without clear communication or a nice compromise (such as, the messy people confines their messes to only one room of the house, into which the neat freak never ever goes unless they’re looking for a fight). Other times we might find something in common that we’re both equally passionate about which is a guaranteed conversation piece.

15 Ask Away: What Are Your Goals?

This is a nice safe conversation starter that can involve goals for the New Year, for the next five years or just in general. A lot of people are very goal oriented and this can be just the question they’ve been waiting for us to ask them. Just remember, according to Conversation Starters World, “Once you have found a topic that you both have in common, spend some time finding out more. It’s a conversation, not an interrogation after all.”

A conversation about goals can easily lead to an interrogation but usually, it just gives us some insight into our date and how they prioritize and organize things in their lives. For the people who whip out their planners or bullet journals right there at the table, we know that they are very passionate about their goals and probably achieve whatever it is they set out to do. If our date just sort of stares blankly at us and says, “I don’t know, I don’t really do goals,” then we’ll probably scare them if we whip out our planner or bullet journal. Might want to save that for the second date if there is going to be one.

14 Ask Away: Do You Have Any Food Allergies?

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While this question comes across as a first date no-no, it’s becoming an increasingly important question to bring up on first dates as the rise of food allergies (some particularly severe to the point of physical contact becoming an issue for the sufferer if their date has touched or eaten something they are severely allergic to).

If we picked the restaurant then we’ll likely pick one that we know and are familiar with the menu, so we won’t have to go hungry for the date but if not, then we’ll have to take extra precautions which can be time consuming and often take some of the fun out of the dating experience.

Not to worry though, online dating is here to save us. According to Allergic Living, online dating sites can make it easier to bring up the topic of food allergies simply by including it in our profiles. “She explains that what brings the site’s users together is a mutual understanding of necessities like label reading and restaurant precautions. Even on big websites such as OKCupid or eHarmony, Carroll notes that online dating can make it easier to put any food allergies out there by including them in the personal profile.”

13 Avoid It: When Do You Want Kids?

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While it is important to let our date know early on if having kids is super important to us or not, it isn’t necessarily first date talk. For those of us who do have kids already and are back on the dating market, we don’t want to spend the whole evening talking about our kids. We should mention if we do have kids as this can be a deal-breaker for some people but then move the conversation along to something else. We can discuss parenting tactics later if needed. Kids can be a dating buzz kill whether we have any or not.

XO Jane words it perfectly,

“This means that I end up talking about babies and marriage very early on, not, as the stereotype goes, because I'm searching desperately for someone to fertilize my eggs before they shrivel up, but because I don't want to get into a relationship under false pretenses..."

"...I don’t see the point in falling in love with someone who has a completely different idea of where they would like a relationship to eventually go, somewhere down the road.” If we do or don’t want kids, we should mention it in the first three dates but not necessarily the first one.

12 Ask Away: Who Are The Most Important People In Your Life?

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Finding out the key aspects of someone’s life (without making them feel like they’re in an interrogation or on a television show being interviewed) is tricky but an important step in forming a lasting relationship. One way to do this is to ask about the people they value in their lives. According to eHarmony, “Pay attention to how your date answers this first date question. How come? More likely than not, they’ll have an instant reaction like, ‘my parents’ or ‘my college roommate’ or ‘my kids.’ In addition to understanding the other person better, this question allows you to assess his or her ability to form close relationships.”

Knowing that our date is can form lasting relationships is an excellent sign in their favor. Plus, now we know who is important to them so if we reach the relationship stage where they bring us home to meet that important person or people, we know how serious they are getting and how crucial this meeting is for them. It’ll also give us a chance to satisfy some curiosity about the people in his or her life that hold such a high position on the roster.

11 Ask Away: What Was Your Childhood Like?

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Depending on who we are dating, this can be a trigger question or a fun conversation starter and we won’t know which is which till after we’ve asked the question so there’s some risk involved there. At any rate, according to eHarmony, this is an excellent question to ask. “Eminent psychologist Karl Menninger said one of the most reliable gauges of a person’s emotional health as an adult was a stable, satisfying childhood. This doesn’t mean — of course — that you should automatically avoid someone who had a difficult upbringing. But you do want the assurance that the individual has insight into his or her family background and has sought to address lingering wounds and unhealthy patterns.”

Since it’s the first date we likely won’t get a lot of nitty-gritty details, but we will get a nice summary and that should be enough to give us a picture of their past.

After all, if we decide to make this a long-term relationship, we will have plenty of time to dive into their past and poke around. In addition to knowing for curiosity’s sake, we’ll also get an idea of how they’ll raise their children through their childhood experiences.

10 Ask Away: What Are You Passionate About?

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Passions, like goals and dreams, vary from person to person. The difference is that dreams are like wishes we can achieve with the help of goals which are steps we use to achieve those dreams. Passions are what get us up in the morning or all excited about something. They can often be interwoven into our dreams and goals but other times they can be unconnected. We can have a dream of traveling to France, a goal of saving up for it and a passion for watching cat videos online. Besides, if our date’s passion is like ours, we will have tons to talk about on future dates.

According to eHarmony, “This question gets to the core of a person’s being. If the individual responds with “I dunno,” that might be a red flag that he or she isn’t passionate about anything. But you’re likely to get valuable insight from the person who answers —from traveling and their children to rock climbing or their church — that give you insight into their value system.” On the flip side, if their passion is wildly different from ours (books versus reality TV), we’ll have to decide if we can make something work out between balancing the two interests.

9 Avoid It: Why Did Your Last Relationship Crumble?

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Variants on this question include probing into past marriages and asking about their exes. Talking about these past experiences is important and will come up naturally later on as the relationship progresses but it’s a no-no for a first date. Nothing sours a nice evening out like a bad memory of someone nasty or a painful wound reopened unintentionally. We want to have fun on our dates and enjoy ourselves as we get to know our new date. Bringing up past relationships can send a nice evening down the drain very quickly and we probably won’t get asked out for a second date if we probe too deeply.

As Bustle puts it,

“Nobody wants to be on a first date listening to a person talk about their last date..."

"...It’s fine to discuss the basics of previous relationships and a general history of your dating past. But keep it vague, people.” It is a different story if our date brings up the topic of their past relationships on their own. They’ll know if they are comfortable enough to talk about it or not and for how long. It’s a bad sign if this topic takes over the conversation and all they talk about is how awful their ex-was to them.

8 Ask Away: What Is Your Dream Job?

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Other variants of this question can include asking what their most fascinating job experience was or what they love about their current job. Chances are good though that everyone has a dream job that they would rather be doing (a few lucky ones are working at their dream jobs which gives the rest of us hope that we can capture that dream and drag it down to reality someday). According to eHarmony, “No matter where they are on the career ladder, chances are your date will have at least one unusual or intriguing job to tell you about. Which will give you a chance to share your own most fascinating work experience.”

Dream jobs can be linked to passions and dreams or they can sprout from a pursued interest discovered further along in life. Some of us filled out homework as kids listing what we wanted to be when grown up while others discovered the answers later in life or while attending college. It’s also interesting to know that sometimes we switch careers after decades of doing the same thing every day. Work is work but it doesn’t always have to be dull and drudgery; it can be fun and exciting if we’re pursuing a dream job.

7 Ask Away: What Are Your Likes And Dislikes?

Always a fun and safe thing to ask about that can shed a lot of light on someone. Likes are fun, easy-going things that make us happy or feel good about ourselves and can range from food to clothes to weather and everything in between. Dislikes are good to know so we can avoid them in the relationship and establish ourselves as wonderful people who buy the candy bars we like and eat the green Skittles for us because we don’t like them. It’s even better when we have similar likes (though competition for the chocolate chip cookies just got intense) and if we have the same dislikes then we are guaranteed to never see another bottle of mustard or bowl of burnt popcorn cross our paths while we’re together.

This simple question forms a nice connection for us. As Huffington Post puts it,

“You meet up with someone to make small talk for a few hours hoping to convince them that you are a fascinating, charming person. Secretly, you are hoping to discover the same about them.”

Sometimes we can even get date ideas out of these likes and dislikes. Bird watching anyone? How about a day strolling through the local bookstore? An evening of superhero films and comics?

6 Ask Away: Do You Have Any Pets?

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This is important to know if we have any pet allergies but also very insightful because people who have pets tend to be more low-key, nurturing and reliable (since they have to be home in time to feed Fido and take him for his walk).

Plus, it can be a great conversation starter, especially if we both have pets. We’ll want to know eventually if they have any pets because introducing pets to each other is an extra step in the moving-in process. According to New York Times, “That’s the bottom line message that women get when they see a man with a dog: He’s capable of nurturing, of giving without receiving a lot, of caring for another. He’s made a commitment to this animal,” Dr. Fisher said. “And one thing women have needed for years and years is a partner who could share the load, be responsible, care for them if they’re sick and show up on time.”

If our cats get along with his dog and no one eats the goldfish, things should go pretty well for us as co-pet parents and for a long-term relationship. We might even get a turtle together!

5 Avoid It: What Are You Looking To Get Out Of This?

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Asking someone right off the bat if what they are looking for is a casual hook-up or marriage can seem like a great time-saver in terms of getting right to the point and weeding out any unwanted people who aren’t on board with our own long-term goals. But the reality is usually the guy or girl panicking and ducking out of the date as fast as they politely can. This is a topic for future dates, not the first one.

As Bustle notes,

“It’s all right to discuss what you want in terms of the future. Saying you would like to get married someday or you are hoping to have children years down the road is completely fine..."

"...Laying it out for the other person isn’t the problem. The problem is when you come on too strong. This is where you start talking about these things in extreme detail.” Dumping all the details of our wedding colors, future baby’s names and where we will ideally live as we raise that future baby or babies is the best way to scare off a perfectly sane date just after ordering the cocktails. Let’s avoid this reaction and enjoy ourselves instead.

4 Ask Away: Are You Religious?

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This is a question that can go both ways. If we are religious, we’ll ask to find out if someone is compatible with us and of a similar belief system. It will save us time, in the long run, to find this out first and avoid fights about it later. If we’re not religious, then we’ll ask to see if our date is, so we can avoid the whole “you need to be saved” conversation. And sometimes it’s just a simple conversation starter. As Glamour puts it, “True, no one wants to hear a sermon. (This goes for non-believers too, as sermonizing against sermons is just another form of preaching.) But if you're looking for a partner—not just a hookup—and if you know that religion is a key criterion, why not test the waters? Life is too short to play coy.”

Discussing similar or differing religious beliefs over cocktails can be quite entertaining, especially when done in a mature non-threatening adult manner. Who knows? We might learn something new that we didn’t know before which can then become a nice conversation nugget on future first dates if this one goes south.

3 Ask Away: What Are Your Thoughts On (Insert Hot-Button Topic)?

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So, we’ve all been told that politics are a first date no-no which is often a very good rule to follow. But sometimes the line between politics and personal morals gets blurred. Politics is usually presidents, Congress, things we vote on and political issues that involve our whole country or other countries. Personal morals are generally more personal and go along the lines of not sleeping together on the first date, never lying if it can be helped, and things of that sort. The topics that fall into the grey area are usually ones like pro-choice or pro-life, vaccines and gun control. Some can be very decidedly political (like gun control) while others are more personal beliefs (like vaccines).

At any rate, broaching this topic should be saved for dessert when things are going well and voiced in a calm non-confrontational manner.

As Your Tango puts it, “Everyone has their own values, morals and belief system and that should not be challenged on a first date. Opposites attract, but if you’re on a first date and political differences come up, “instead of converting your partner, consider listening and learning,” says relationship expert April Masini.” We want to get to know our date, not scare them off.

2 Ask Away: What Is Your Family Like?

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This is also a sneaky way to find out if they have kids without directly bringing it up. According to Huffington Post, “I would find a way to ask your date about how close they are to their family. I see many divorces caused by one person being so close to their family that they prioritize them over the marriage and have poor boundaries: Once you are married, your marriage must be protected and prioritized over the relationship you have with your family of origin.

On the flip side, bad family relationships can be a sign of personality disorders and an inability to sustain relationships in a long-term way.” Finding out about someone’s family and whether they get along and how close they all are is important for long-term relationship survival. Plus, if they have kids they’re keeping mum about, we’ll want to find out at some point. If his family plays Scrabble once a week, that can sound a lot more fun than our family’s weekly argument over mimosas every Sunday night and vice versa. He might not like that mimosa-fueled argument session and will wonder why we still hang out with our family.

1  Avoid It: You’re Not Crazy, Are You?

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This is a no-no question for obvious reasons. As Best Life puts it, “Followed by something like, ‘I’ve been meeting a lot of crazy people lately.’ Yikes. ‘Though this might sound cute, it can come off as strange to your date,’ says Candice A, a certified matchmaker and dating coach at Toronto Wingwoman. After all, they might start to wonder why you’re meeting so many crazy people in the first place.”

We don’t want our date to wonder if we’re the crazy one here.

On the other hand, we really don't want to get all involved with someone who is crazy, but we can’t just outright ask them on the first date. It sends the wrong message. Wait for a few dates further, observe their behavior closely in different settings, listen to their stories of how they reacted to an ex or a family member, then gauge their crazy level based on the facts gathered. Or if the relationship has progressed far enough, ask them in a gentle non-threatening manner if they have a history of mental illness in the family. Ask sometime after the first few dates but before the wedding bells ring.

References: Conversation Starts WorldHuffington PosteHarmonyAllergic LivingHuffington PostNY TimesGlamourYour TangoHuffington PostNY TimesXO JaneBustleBest Life, Toronto Wingwoman, eHarmony, Your Tango, Ask April

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