✌🏼20 Questions You Need to Ask to Take Your Online Dating Fling to the NEXT LEVEL

While online dating is at an all-time high, it is important to ask the right questions if you want to get the most out of your experience. If you’re just online dating for fun there is nothing wrong with that, but it’s best to let the person know your intentions. If what you’re looking for is something more serious, you may be worried it will be hard to get anywhere considering the lack of face-to-face contact. Well, quite the contrary! All this time texting and speaking over the phone can allow you to dig deeper and get to know the true person you’re talking to.

Here are 20 must-ask questions while online dating that will help take things to the next level:

  1. What’s one thing you want to ask me, but you’re too nervous too?
    This is a great question to flip things around and find out what they are wondering about you.
  2. How important is space in a relationship for you?
    Whether you’re someone who likes to be with a significant other 24/7 or you value your alone time, it’s important to know if this is something you agree about early on.
  3. Why didn’t your last relationship work out?
    Don’t get into talking about exes for too long. Trust me, no one wants to hear it. But, this question will give you the answers to some key information. Do they cheat? Are they not into long term relationships? Did they feel suffocated? So many details, so little time!
  4. What’s your love language?
    Finding out whether they prefer words of affirmation or physical touch as a source of love can help you know how to treat one another down the line.
  5. Where do you see yourself in five years?
    Don’t you want to know if your futures can align?
  6. How do you prefer to communicate?
    Isn’t it better to know now if they aren’t good at texting or don’t prefer facetime calls to phone calls? It can help you not feel so in the dark when waiting for a response. Be sure to let them know how you feel about this as well so you can find common ground.
  7. What’s the best vacation you ever took?
    See if you are compatible when it comes to travel. Did they say when they went hiking up the mountains or spending a week laying on the sand?
  8. What would be the first thing you’d do if you won one billion dollars?
    If they respond with, “I already have a billion dollars,” don’t ask any more questions and just marry them.
  9. What’s something you did a year ago that is a little embarrassing to you now?
    This will help you see how they evolved as a person in the past year.
  10. What is your best friend like?
    Unfortunately, it’s likely you won’t be meeting the best friend anytime soon, but it’s very telling the kind of person they describe to you. Will you get along? Is it sweet the way they talk about their friends?
  11. Do you have or want any pets?
    Better to know now than later. This is a big deal-breaker for some people.
  12. What’s your favorite movie and favorite television show?
    Don’t you want to know if God forbid we are ever quarantined again in the future you won’t be arguing over which shows to watch?
  13. How do you feel about [insert a recent news topic you have an opinion about].
    Don’t you want to know how their opinion stands with yours? You can see if you can both have a healthy debate or maybe they don’t have any opinion at all.
  14. What’s a food you hate irrationally?
    Throw this one in there for some good fun! Find out if they are a “psychopath” who can’t stand the texture of avocados or something. Just kidding of course. We are all entitled to our own opinions…
  15. What’s the last thing that made you laugh so hard that you cried?
    Best case scenario they tell you a story and you both crack up. Worst case scenario they tell you they never laugh that hard and you run for the hills.
  16. Ask them their opinion on a small crisis in your life?
    Fighting with a pesky roommate or having some issues with work? Asking them will give you an idea of what having a real relationship will look like. You can get an idea if they will be the type of partner that will give you good level headed advice.
  17. Are you a morning or a night person?
    You might want to find out if they are the type who you will stay up having conversations with until 3 A.M. or if they’re in bed early because they hit the gym at 5. A.M. (I once asked a guy what he was up to as I was eating leftover pizza at 9 A.M and he told me he just finished a 20-mile run…yes…20 miles. The dating did not continue.) 
  18. What are the top three things on your bucket list?
    Find out and make note of it. Maybe you will have similar ones or can one day experience them together!
  19. What’s the last good thing you read?
    If they hit you with, “I don’t really read much, but I do love playing my video games,” you might want to mark this one as a fling and not expect a ring. HALLELUJAH!
  20. Do you like your job?
    It may seem trivial, but it is important. I once dated someone who hated their job so much that they did for the high paycheck, but it made them so miserable it was hard to be around them sometimes. A question like this can help you see how motivated, optimistic, or lazy they are.


“Online dating…Where you meet and break-up with someone without ever leaving the house.” -Unknown


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