The Essential Questions to Ask on a Dating Site Before You Meet Up

Co-authored by wikiHow Staff

Last Updated: November 23, 2021 References

Online dating has become one of the most popular ways to meet people for a potential romantic partnership. But that doesn’t mean that it isn’t sometimes a little awkward! Having some good questions on hand will help you develop chemistry and learn more about the person on the other end of the screen. We’ve compiled some tips on what questions to ask, as well as some additional bits of advice, to help you navigate the world of online dating and have fun while doing it!

Method 1

Method 1 of 15:
“What have you been binge-watching recently?”

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Getting people to talk about their interests excites them. Asking about the movies, books, and music they like also gives you a new way of getting insight into a person! After all, most of us aren’t all that great at describing and evaluating ourselves objectively. It’s easier to get a look at someone’s thought process by asking them about their thoughts on art.^{[1]
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Research source} Ask them:
- “Have you seen this new show that everyone’s talking about?”
- “I watched this crazy movie last week. Have you seen it?”
- “You said you like Marvel movies on your profile—did you see the latest one?”
- “What’s a movie you liked recently?” Simple questions are much easier to answer than more difficult ones, like “What’s your favorite movie?”.

Method 2

Method 2 of 15:
“What would you do if you met your clone?”

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Having a sense of humor is something most people look for in a potential partner. Get an idea of someone’s sense of humor ahead of meeting them by asking them a hypothetical or weird question!^{[2]
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Research source} These kinds of questions give the person you’re talking to a chance to be a little witty, so try out these examples:
- “How would you react in a zombie apocalypse situation?”
- “Aliens—real or not?”
- “Weird question, but should we be afraid of AI?”

Method 3

Method 3 of 15:
“Would you rather?”

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Use this classic and light-hearted game to get to know someone. Playing a couple of rounds will let you see how the person you’re talking to relates to things they like and dislike, and can be another great way of bringing some fun into your conversation.^{[3]
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Research source} Some example questions are things like:
- “Would you rather eat your least favorite food for every meal, or hear your least favorite song on repeat constantly?”
- “Would you rather have telekinesis or telepathy?”^{[4]
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- “Would you rather find true love or win the lottery?”^{[5]
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- “Would you rather have to spend a week in the woods or a night in a real haunted house?”^{[6]
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Method 4

Method 4 of 15:
“What was it like where you grew up?”

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Where we grew up has a huge impact on us. Many adults have positive memories about their hometowns, and bringing up these memories can be a great way to open a conversation.^{[7]
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Research source} Try asking:
- “What was it like growing up in LA?”
- “Why did you leave Canada?”
- “Do you ever miss Houston?”

Method 5

Method 5 of 15:
“How do you spend your time?”

1
Get to know someone’s daily routine to paint a picture of them. Asking someone how they spend their day is a simple and straightforward question, but definitely a useful one.^{[8]
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Research source} You can really start to understand how someone approaches their life, so try one of these questions out: ^{[9]
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- “How do you spend your mornings?”
- “What do you do after work?”

Method 6

Method 6 of 15:
“Got any hobbies?”

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Find out what your match is passionate about. People often list their hobbies in their profile, so this is a great chance to get them to talk about why they matter to them, or to find something you have in common.^{[10]
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Research source} Use some of these questions to get your match to open up about what makes them unique:
- “You like cooking, right? What kind of food do you make?”
- “I like photography too! Got any tips on what makes for a good pic?”
- “Send me a pic of your dog! What’s she like?”

Method 7

Method 7 of 15:
“What are your dreams?”

1
Talking about someone’s dreams can help you understand what things they value. Learning about their career aspirations, dream travel destinations, and life goals lets you go beyond first impressions.^{[11]
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Research source} Try asking:
- “What’s something that you want to do in life?”
- “What would you do with your time if you could quit your job?” An ambitious person might say they dream of opening their own business, while a more relaxed one might instead want to be on a beach in Mexico. Knowing this kind of information about someone can help you decide if you’re compatible.
- “What would you do if I gave you a million dollars?” This is a more playful version of the classic “What would you do with a million dollars?” question, and can make your conversation a bit more unique.

Method 8

Method 8 of 15:
“What do you think I should do?”

1
Talk about a simple issue you’re having at work or in your personal life. People enjoy giving advice. Their advice may or may not be useful, but it’s a great way to see how they try to make themselves helpful.^{[12]
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Trustworthy Source
Harvard Business Review
Online and print journal covering topics related to business management practices
Go to source} Stay away from overly complex or difficult situations and try out questions like these:
- “Any advice for dealing with a tough boss?”
- “My mom’s upset I can’t make it to her anniversary party. What would you do if you were me?”
- If you’re going to your nephew’s birthday party, for example, message them with “Know any good gifts for an 8 year-old boy?”

Method 9

Method 9 of 15:
“How has the site been for you so far?”

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Something you already have in common is that you’re both trying out online dating. This can be a great place to start a conversation!^{[13]
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Research source} If you’re struggling to come up with a way to talk to the person on the other end of the screen, just remember that you both are looking to find companionship. Try asking something like:
- “What do you think of this site so far?”
- “Met any cool people on here yet?”
- “How’s dating been for you?”

Method 10

Method 10 of 15:
“What’s the most important thing I should know about you?”

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Give your match the chance to get serious. Being straightforward can pay off sometimes, and could take your conversation in a deeper (and rewarding!) direction.^{[14]
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Research source} Message them something like:
- “Is there anything you want me to know about you?”
- “Could you tell me about what kind of person you are?”

Method 11

Method 11 of 15:
“What’s your most controversial opinion?”

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Fish for red flags to weed out people you’re not compatible with. Asking them a question about their most provocative beliefs can keep you from investing too much time in something that won’t work out. Or, you might find that you share something in common with the person you’re talking to!^{[15]
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Research source} Ask them something like this:
- “Got any unpopular beliefs?”
- “What’s something about you that makes people mad?”
- “What’s the weirdest thing you think is true?”

Method 12

Method 12 of 15:
Ask follow-up questions.

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The best questions are ones that flow naturally from your conversation. Researchers have shown that asking a lot of questions is one of the easiest ways to be more likeable and to make a good impression on someone else. Don’t be afraid to ask for more details about things that the person you’re talking to already mentioned.^{[16]
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Research source} Try something like:
- “I wanted to bring up something you mentioned earlier…”
- If the person you’re talking to mentioned liking U.K. football teams, shoot them a message like, “Arsenal or Liverpool?”
- If they mentioned being close to their family, ask them something like, “What’s your relationship like with your siblings?”

Method 13

Method 13 of 15:
Send shorter messages to catch people’s attention.

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Keep your opening messages to under 40 words. We all want to express how we feel in all the detail it deserves, but in online dating, concision is king. Unfortunately, studies have shown that lengthy introductory messages are often ignored.^{[17]
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- Don’t be discouraged if you don’t get a response to a message you sent out. People can get busy, and sometimes people leave dating sites altogether without their profile updating. If you don’t receive a response in a couple of days, move on to the next option.^{[18]
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Method 14

Method 14 of 15:
Save personal questions for when you talk face-to-face.

1
Try not to bring up negative experiences online. Asking someone questions like “Why are you still single?” or “How did your last relationship end?” might be well-meaning, but can be painful to the person receiving them.^{[19]
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Research source} Steer away from questions about past relationships, money, or drugs. You want to get to know the other person, but don’t want to dig up any painful memories.

Method 15

Method 15 of 15:
Move the conversation to a video call or in-person meeting.

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The best way to start a new relationship is to meet soon. Research has shown that when people message online for too long, they can build up idealized images of the person they’re speaking with, only to find that the person doesn’t quite match up in real life. You need the reality-check that comes from having a real-time conversation with someone in order to understand that person, so after a couple of weeks at the maximum, it’s likely time to meet!^{[20]
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