First dates and getting to know someone is always a little awkward. But with the uncertainty of online dating, questions about meeting someone in person and planning for a first date are bound to come up.

To make the most of an uncertain encounter, you’ll want to ask the right first-date questions straight away. Thoughtful questions help reveal a lot of information about your date and will help the typical, yawn-worthy direct questions that everyone seems to rely on.

20 Online dating questions you should ask

Dating and Relationship Expert Carol Roderick, MEd, PhD shared her insights when it comes to thought-provoking questions to ask on a first date. Questions that are equally interesting and fun will help foster a sense of lightness throughout the date while still giving you both the chance to get to know each other beyond the surface.

1. What would you need to feel safe meeting up in person (if you haven’t already)?

The biggest potential downside of online dating is it requires meeting with someone you barely know. This is risky for everyone, especially women.

But with video conferencing technology now a common occurrence in both our personal and professional lives, many people opt to have their first “dates” this way as a bridge between chatting online and meeting in person. If you’ve chosen to go this route, asking the question is an important courtesy.

“Finally, if things are going well with a virtual date, this is a MUST ASK question if you want to take it to the next level,” explained Roderick. Most people will be comfortable with basic safety precautions, like meeting in public during normal hours and arriving independently.

2. How was your day?

This is a question we typically would ask a good friend. It creates an instant connection.

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3. What do you think of meeting men/women this way?

According to Roderick, everyone can relate to this question, and it makes for easy conversation right off the bat. After all, online dating of any kind is a relatively new phenomenon for most of us.

4. What do you like about connecting through an app vs. more traditional means?

“This question sets each person to look at the situation in a positive light, which is where we want to keep things, especially on a first date,” Roderick said.

5. What’s a funny (but innocent) mishap that’s happened with online dating?

Anyone who’s tried dating apps or websites for a while has had any number of quirky setbacks, be it matching with an ex or arriving at the wrong date location. Laughing over shared experiences is a good way to foster an early connection.

6. What do your Saturdays usually look like?

“This allows each person to get a glimpse into the other’s everyday life and see if you can imagine yourself in it. Is it a fit or not,” Roderick said.

7. What are some fun or interesting things you do on a rainy day?

According to Roderick, this gives you a chance to see how a person creatively responds to life’s curve balls. She suggests you keep the question open by asking about “some” fun or interesting things rather than the “most” or “best.” When we have to think of one item only, it can make someone’s mind go blank, especially if you are already nervous because it’s the first date

8. What’s been the most significant plot twist in your own life?

“Key turning points in one’s life reveal how a person is under stress and transition,” explained Roderick. “Do they crush under pressure or go with the flow and have a sense of adventure?”

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The phrase “plot twist” rather than “setback” or “hardship” is positive framing, which allows them to decide how forthcoming they wish to be about their lives.

9. Do you have any guilty pleasures?

This question speaks to a person’s values. “The only reason we feel guilty about something is that it runs counter to our value system,” said Roderick.

“For example, if chocolate is a guilty pleasure it is fair to deduce that the person likely values healthy eating.”

10. What is your motivation to get out of bed in the morning?

Another option is “what keeps you up at night?” It provides insight into the person’s priorities and what they care about.

11. What is your favorite TV show or movie and why?

The TV shows or movies you like can be revealing about your character. If an action movie is your favorite, then you likely have an adventurous spirit. Or, if your favorite is a romantic comedy, you likely want to understand how people tick, and value intimacy and time together.

“Knowing a favorite TV show or movie also lets you know whether you will actually enjoy cuddling up in front of Netflix together or whether you’ll want to exit the room.”

12. Do you have any pets?

“Animal people love to talk about their pets, and share photos and related stories. This could also be a deal breaker if one of you is allergic to pet dander,” Roderick said.

This is also a measure of their conversational skills—pets are pretty easy to talk about, and if they can’t that’s either a sign that they aren’t much to talk to, or a connection just isn’t happening.

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13. Do you like traveling or do you travel often?

This gives you insight into their lifestyle—curious and down-to-earth, or prim and high maintenance? Does your date enjoy weekends away camping locally and time outdoors? Meeting people and taking in local culture in far-flung countries? Or are they into first-class travel with all amenities?

14. What is your favorite childhood memory?

“Even if our families weren’t perfect, people tend to love sharing and reliving moments of their childhood,” explained Roderick. ‘It creates nostalgia and gets our happy hormones all juiced up.”

15. What do you like to read about?

What you read for fun says a lot about your interests, emotions, and self-esteem. “If you are into self-improvement books you are likely someone who is always learning. If you prefer fiction you might like diversion and have a playful imagination,”

16. What is the most interesting place you’ve ever been to?

“What is important is not so much the specific location but what you loved about it and what captured your attention,” said Roderick. “It’s all in the details.”

17. Where did you grow up?

Like asking about favorite childhood memories, this question usually elicits positive memories and allows us to share something meaningful and personal about our lives.

Though be aware, if they didn’t have a positive childhood, they may not want to talk much about it, and that’s okay.

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18. Who is your biggest role model?

Is it their mom/dad, a favorite teacher, a celebrity or a public figure? “This tells you whether they look for inspiration close to home or are inspired by what is going in popular culture and the world around them,” Roderick said.

19. What’s on your bucket list?

According to Roderick, this question also speaks to values and aspirations. What to do they want to accomplish in life? What do they want to contribute?

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20. Do you have any current goals or plans?

“Maybe they are taking off to go out of the country for six months—you certainly want to know that!” said Roderick. “But really, it gives you a sense of how they might be working toward actually achieving their bucket list.”

First-date questions to avoid

Just as some questions can be revealing and help further a connection if one’s already brewing, some questions can take a conversation down the wrong path—and quickly. Basic topics like money, politics, and religion are best left for later dates; they should also be avoided at the first meetup.

Do you want to have children and a family?

First dates should be breezy and fun. It is all about deciding whether you have enough chemistry and enough in common to want to get together again.

“When you ask about children and family, the tone shifts to job interview mode,” explained Roderick. “A date is not about finding someone to fill the job vacancy of mother or father to your future children. It is just too much too soon with someone who is a stranger.”

Where do you see your life five years from now?

“In the same way as asking about children and a family, this question gets us into a planning and action mindset rather than creating a conversational space of relaxation, fun and the opportunity to be really present in the here and now with each other,” Roderick said.

Any questions that would be frustrating in a job interview are even more frustrating on a date, and should be avoided.

How many people have you slept with?

This question will get you talking about sex on the first date. For most people, this is far too soon. But even if that’s where things are heading, this isn’t a valuable question.

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Everyone has a past, and that’s only going to be pertinent to people with certain cultural and/or religious backgrounds and values—something that should probably have been made clear before the question arose. For everyone else, there’s no answer to this question that will satisfy them.

You’re great. Why are you still single?

According to Roderick, when a man asks this question, they are thinking “Wow—you are such a catch, I can’t believe my luck. I can’t believe that you haven’t been swept up by some other guy.”

Unfortunately, when a woman receives this question, the voice in her head may have her wondering what’s wrong with her—“hey, why am I still single?”

If a woman asks this question, she may be genuinely suspicious. She thinks there must be something wrong with you… what is it? Regardless of whom it’s coming from, it’s a bad idea.

How is dating going for you? What dating apps are you on?

Both men and women can be tempted to ask this question when they want to dig in and find out more about how their data is approaching dating—have they been dating for a while or are they newly single? Is their date going out with many other men/women casually? Are they seeing anyone else?

“Asking this question just stirs the pot and tends to have the date slide downhill,” explained Roderick. “When you step back and look at the question, the answer is actually irrelevant. If you two are going to have a future, the rest doesn’t matter.”

What are you looking for? What is your ultimate dating goal?

“While you might be curious to know if you are on the same page, it is hard to strike the right tone in an answer,” Roderick said. “The risk is one of you comes across as coming on too strong and the other starts to feel, at an instinctual level, like they are being chased or hunted.”

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According to Roderick, when we feel that way, our gut tells us to run away quickly. If you receive this question, be honest but soften your approach. If you are looking for your soulmate, try, “I’m looking for a long-term relationship, but with the right person.”

What are your deal breakers?

While important to know, Roderick suggests allowing it to come up naturally. Asking what your deal breakers are is like asking someone to pull out a clipboard and pen so you can check off the various boxes or not. Again, this is not a job interview.

Tips for a safe, fun online date

Even if you took the extra step of having a virtual meet-and-greet to better get to know your match, in the end, you’re still meeting a strange person for a date. In order to both have fun and stay safe, consider the following.

Meet in a public place

Rule no. 1 for any first date is to meet somewhere in public, not at anyone’s home. This offers an extra layer of security should things go awry, as well as more options for help. It’s best to meet at the venue independently as well, so as to not reveal too much about where you live.

Make enjoying yourself a priority

We all know first dates can be awkward—and online dates only add to that, but focusing on fun, having a good laugh, and just trying to make it an enjoyable experience will go a long way.

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Keep others informed

When meeting for the first time, at least one other person should know where you’ll be and how long you expect to be out. It’s also a good idea to keep them updated as the date goes on—a discreet text message when your date uses the restroom, for example.

Research your date

While it might not be as spontaneous or romantic, taking the time to look up your date (whether with a people search or a search engine) to see if there might be any potential red flags, whether in their social media presence or otherwise.

Acknowledge the awkwardness

Be honest: Meeting a new romantic interest can be uncomfortable. Whether you hit a few snags in the conversation or you’re having a hard time breaking the ice, just lean into it and acknowledge how strange it is. Simply acknowledging the awkwardness can break the ice and get any weirdness out of the way.


Asking the right questions that foster a sense of genuine interest will instantly create connection and relatedness, giving each person a sense that they are already familiar with each other while putting both of you at ease.

According to Roderick, this will also set the tone for a more relaxed unfolding to the date altogether. “When this line of questioning is used, each person leaves the date with the impression that ‘it feels like I’ve known him/her for ages… I can’t believe we just met.’”

This article is republished with permission from Melan Villafuerte, the Content Specialist at This article originally appeared on

Disclaimer: The above is solely intended for informational purposes and in no way constitutes legal advice or specific recommendations.