Hi, how are you? So, can you tell me about yourself? 

Two of the most useless questions for online dating, yet so many people still ask them! (And honestly? There are much better questions to ask to get to know someone.) 

Online dating is about getting to know people, see if there’s an initial indication that you may be a good match for each other, and then take it further. If the answers indicate you aren’t a good match, then you scroll on. It’s fast, and every question should count.

Reasons Why You Can Trust Krystyna

When Is It the Right Time to Ask Questions When Online Dating?

Asking questions is how you learn information about people; however, you don’t want to feel like you are bombarding the other person with questions. It’s an online date, not an interrogation. 

The right time for questions is to ensure you ask questions in a mutually beneficial way. Ask and listen to the other person, opening room for discussion and sharing ideas. 

online dating questions to ask

Don’t rush off a list of questions, without waiting for responses. This is how you know it’s the right time for an online date question (or ten). 

Questions are conversation starters, so let the conversation flow.

The 20 Most Interesting Questions to Ask a Girl Online

A rule of thumb when asking questions of a lady you’ve met online is to remember that you don’t know her yet. Don’t be overly familiar or creepy with your questions, and avoid implying you expect things to go for home base. 

At this stage, you are simply finding out about her, learning what she likes and doesn’t like, and who she is. Stick to those parameters for your questions and you’ll be fairly safe and almost guaranteed to get stimulating responses that you can build further questions on. 

1. What made you swipe/click on my profile?

  1. So tell me about your day? What have the last 12 hours been like? 
  1. Are you fond of animals? Which animals do you like? Why do you like those? 
  1. Do you like the job you do, and why?
  1. Do you have any brothers or sisters? What are they like? 
  1. How do you decide whether you will like someone?
  1. If you could go on holiday or vacation right now, where would you go? 
  1. Which do you prefer: a home theater in your backyard with pizza and root beer, or a fancy evening at the local Italian restaurant? 
  1. Are you a mommy’s baby, or Daddy’s little girl? 
  1. Who is your favorite motivational speaker, or what’s your favorite uplifting quote? 
  1. Are you a driven person, and what motivates you to get out of bed in the morning? 
  1. What is an absolute relationship breaker for you? 
  1. If you had a superpower, what would it be, and how would you use it? 
  1. Where do you see yourself in five years’ time? 
  1. If you had to choose between money, love, and success, which would you choose and why?
  1. What are your favorite hobbies to practice? 
  1. If your car has a flat tire next to the road, would you fix the flat yourself or call the AAA?
  1. If you could chat with any celebrity online, who would you most like to chat with?

19. What is your favorite dessert to have?

The 20 Most Interesting Questions to Ask a Guy Online

With many online dates still aiming for a quick hookup, it’s best to play it safe and stay a little aloof and mysterious in your questions to the guy you’ve just met online. You’re not dating yet. He has just responded to your first few messages, not proposed marriage. 

Don’t overshare by asking sensitive questions that he may not want to answer. If you ask about money or status symbols like what kind of car he drives, he will think you’re just after his money.

what to ask guys online dating

The whole point of asking him questions is to learn about him, get him interested in you in a healthy and respectful way, and make a connection. 

  1. What did you find most interesting about my online profile that made you choose to swipe right? 
  1. Do your best friends have a nickname for you? What’s the story behind it? 
  1. If you had a bucket list, what three items would be on it and why?
  1. Do you prefer muscle cars or the outdoors? What’s the appeal?
  1. What is your first childhood memory and how did your childhood make you who you are today? 
  1. What is the punishment for someone who orders pineapple on pizza?
  1. Would you consider becoming vegetarian if your partner is anti-meat? How would you explain your decision to them?

8. How would you plan a romantic date with the girl of your dreams if you had a thousand dollars to spend, and how would you plan one if you had less than a hundred bucks to spend?

  1. If you had to come back as a ghost, who would you haunt and why?
  1. What matters the most to you: integrity or popularity? Why is it most important to you?
  1. How would you tell someone you love them without saying it aloud?
  1. If there is such a thing as reincarnation, what or who would you like to be reincarnated as?
  1. Where do you find your inspiration and your place to reload your mental and physical batteries? 
  1. When is it okay to lie to your partner, and how would you explain it if they found out you lied to them?
  1. Are you the type of person who prefers to be early, or are you often late? What do you think of people who are late (if you’re always early) or always early (if you’re always late)?
  1. Would you prefer to go to a basketball game or hang out with your friends for local poker night? 

17. How old were you when you started to drive?

  1. Breakfast is an important meal, but what other meal is your favorite of the day?
  1. When you stay in a hotel, what do you look at to determine the quality of the rooms and services? What are non-negotiables to you about a hotel?
  1. Do you prefer an eye-for-an-eye world or a turn-the-other-cheek world? 

The 20 Bad Questions NOT to Ask Your Match Online

Boring questions like “hi, how are you” or “I’m Stephani, wanna chat?” are not going to get him interested in you. However, asking deep and provocative or offensive questions of someone you just met online will also not win the right kind of date over to your side.  

Personal questions that may appear judgmental or prying may also not work in your favor. Nobody likes to feel like they are being “approved” by someone they just met. 

Talk about a major relationship red flag

  1. Why did your last relationship not work out? (#soinappropriate) 
  1. Do you believe in love at first sight? Or do I have to scroll past again? (#creepypickup)
  1. How much money do you earn, and how are you spending it? (#golddiggeralert)
  1. Do you believe in heaven, and what do you think hell will be like? (#waytoodeep)
  1. Who did you vote for in the last elections? (#noneofy’allbusiness)
  1. Where do you see yourself in 10 years’ time with family, work, money, and future goals? (#likereallytoomuch)
  1. Can I have a photo of you in the nude? (#prematureflirter)
  1. What type of sex do you like, and when do you go for homebase in your relationships? (#onetrackmind)
  1. My grandmother is really ill, and I am selling raffle tickets for her care—would you buy some? (#scamartistalert)
  1. Have you tried other dating sites, and how successful were you there? (#phishingforinfo)
  1. Would you ever date a (race/religion/culture) person, or have you already done so? (#racialprofiling – unless you are on an interracial site)
  1. Where do you live, and can I come over? (#serialkillerwarningsigns)
  1. I never have any luck with these dating sites, and nobody ever agrees to a date, but would you like to meet in person? (#negativenate)
  1. What was your childhood like, and what do you regret about it? (#tooearlyforemotionalbaggage)
  1. What is your perfect date ideal? How do I measure up? (#youjustmetcreep)
  1. What is your deepest secret? (#toopersonal)
  1. When are you having kids? (#stereotypical)

18. Why are you still single? (#sorepoint)

  1. What level of education did you reach? Why didn’t you finish or go to college? (#snobbystatusconscious)
  1. When can I expect you to message me again? Can we call and chat in person? (#movingtoofast)

The Final Question

Dating is never easy, and getting to know people for the first time can be awkward as hell, whether online or in person. 

Having a few tasteful and carefully phrased questions can help you connect, gather some more information about the person, and decide whether you are indeed interested in chatting more. 

To ensure success, make sure your questions are appropriate to the first date, asked in an open manner to encourage answers, and consider the other person’s potential interests and feelings.

If you want to learn more about questions to boost your intimacy when your first date moves to a future date (or ten), read my guide on building intimacy with couples’ questions

Happy quest-ioning.

Krystyna Trushyna
Krystyna is a blogger, coach and iDate speaker. She has been working in online romance and International dating industry since 2012 and is passionate about identifying the romance scam and giving dating tips and hacks. Join Krystyna for the dating service reviews and for finding ways to succeed with dating.
Krystyna focuses on International dating, which involves teaching men communication skills in a cross-cultural environment. She has been featured in many major publications including Space Coast Daily & SWAGGER Magazine.
Looking for more information? Feel free to get in touch to ask your questions or give feedback (see here: Contact Krystyna).