Online relationships are difficult, and that’s a pure fact. The most important online dating tip every dating expert will give you is that you need to keep in touch regularly if you want things to succeed.
With the help of these amusing online dating questions, you’ll most assuredly spark some interesting and enjoyable conversations. And, of course, you’ll get to know everything you want to know about your online date before meeting them IRL.
Also, these interesting questions are a great way to make a great first impression… to win over your online dating partner even before you meet face-to-face.
Let’s arm you with some amazingly fun questions, so your online dating conversation never becomes boring.
Ice Breaker Questions For Online Dating
Were you scrolling through Tinder, Bumble, or another online dating app and one particular online dating profile caught your eye? Did you see that you share many similar interests and likings with that person, and that you would make a pretty compatible couple?
And, even though you have the guts to reach out first, you don’t know how to do it. Starting a conversation was never your thing.
I get you; I really do because that is my weak side, too. To help you, myself, and all people like us, I compiled this list of great icebreakers for online dating.
1. Your dog is amazingly cute. What’s its name? (You’re also not bad looking yourself, BTW.)
2. Have you been reading anything interesting lately?
3. If you could change the world in one way, what would you change?
4. What is your favorite season, and why?
5. If your life had a soundtrack, what song would it be?
6. Tell me your life story in five emojis.
7. What’s the strangest nickname you’ve ever been given, and how did you earn it?
8. Quick: What is your go-to pizza topping?
9. Have you ever had a celebrity encounter? Describe what happened.
10. So, I see that you’re a Yankees fan. Would the fact that I root for the Red Sox keep you from talking to me?
11. It’s Saturday morning. What’s the first thing you do when you wake up?
12. Are you more productive at night or in the morning? Do you think it’s possible to change and get used to another schedule?
13. Where was that third pic in your profile taken? It looks beautiful there!
14. What was the most beautiful place that you have ever visited, and why?
15. What is the first song that pops out on your playlist?
16. If you were a character in a book, how would the author describe you?”
17. Important question: What do you think is the best way to prepare for a zombie apocalypse?
18. I see you’re into traveling! If you won an all-expense-paid trip to anywhere in the world, where would it be?
19. What kind of challenges are you facing these days?
20. Have you ever read your horoscope? What is your sign?
21. What are you watching on Netflix these days?
For more effective and amusing online dating icebreakers, you should check out this collection of good conversation starters.
Best Online Dating Questions
What do you think? Is it possible to meet someone before the actual meetup happens? Well, it sure is.
You only need to ask the right questions and you will be able to get to know a person without even meeting them in real life. And, thank me later, I’ve listed those questions right here below.
1. If you could choose a superpower, what would it be?
2. Who’s your favorite movie character? What do you like about him/her?
3. Would you rather be crazy rich or deeply in love?
4. What’s something you despise that is loved by everyone else around you? Conversely, what is something you love that everyone else seems to hate?
5. What do you like to do on a first date?
6. What have you done that you’re most proud of?
7. Would you rather have telekinesis (the ability to move things with your mind) or telepathy (the ability to read minds)?
8. Dating Apps vs. Matchmakers: Which is better?
9. What’s the one thing you can’t tolerate?
10. What’s the most recent thing you’ve done for the first time?
11. What are the top 2 social media apps you use?
12. What’s your favorite movie or television show?
13. What is something everyone always gets wrong about you?
14. Is the idea of a spontaneous date interesting to you?
15. If you could describe yourself with one word, what would it be?
16. What’s something on your bucket list you think you’ll never actually do?
17. If you died today, what would your greatest achievement be?
18. If you could make everyone in the world believe one thing (regardless of whether it’s true or not), what thing would you choose?
19. What are you so incredibly terrible at that you’ve given up ever doing again?
20. What’s the nicest thing someone has ever done for you?
21. How many times has your heart been broken?
22. What values are most important to you?
23. If you were given the chance to make your one wish come true, what would it be?
24. What was the biggest realization you had about yourself?
25. Which do you listen to the most: your heart or your brain?
26. What three things did your past relationship teach you?
27. Are You Spiritual Or Religious In Any Way? If So, How?
28. What work would you do if you had enough money to not have to work ever in your life?
Funny Online Dating Questions
According to dating coach, Amy Nobile, the key to successful flirting on dating sites is warmth and positivity. I couldn’t agree more with her because humor is really the most powerful flirting tool.
For all online daters, leave a positive first impression with these fun questions to ask your online match.
1. Would you rather have toes for fingers or fingers for toes?
2. If you were an animal, what would you be, and why?
3. What is the dumbest way you’ve been injured?
4. What’s the craziest bet you have ever made?
5. What personality trait has gotten you in the most trouble?
6. If you were a flavor, which one would you be?
7. Which fictional character would be the most boring to meet in real life?
8. What is the stupidest thing you’ve done in your entire life?
9. What’s the most embarrassing story from your childhood?
10. What’s your favorite cheesy pick-up line?
11. What’s the most foolish purchase you’ve ever made?
12. If someone painted a portrait of you, how would it look (clothes, background, pose, etc.), and what else would be in the painting with you?
Online Dating Questions To Ask Him
If you have just met a boy on some dating site and started chatting with him, I have one important piece of advice for you: Don’t make him feel as if he’s being interrogated.
It’s okay to ask some follow-up questions while you’re talking about something, but you need to keep the convo casual. Here’s a list of great questions that will help you keep the conversation going smoothly.
1. What about my profile made you decide to swipe right?
2. How long was your last relationship?
3. If you fall for someone, do you wait to say so until it feels socially appropriate, or do you just spill your guts?
4. What do you expect from an online relationship?
5. What is the one thing you always notice first about a woman?
6. What childish thing do you still enjoy?
7. What’s the next goal (big or small) that you want to accomplish in life?
9. What do you think the best thing about being in a committed relationship is?
10. What’s the worst and best thing about being male?
11. Are you a show-off when you like a girl or do you play it cool?
12. What was the first thing that came to your mind the first time you saw my online dating profile?
13. What’s the weirdest thing that has ever happened to you on a date?
14. Do you like it when a girl makes the first move?
15. Would you be jealous if you saw me flirting with another guy?
16. What is one thing a woman can do to instantly impress you?
17. What’s your favorite kind of date?
18. Have I ever done or said anything to upset you?
19. What is one thing a woman can do that would instantly turn you off?
Online Dating Questions To Ask Her
For all online male daters, check out this list of great online dating questions to ask girls on dating websites. These interesting and deep questions are guaranteed to help you win over any girl you like.
1. Do you use social media?
2. What would you like to do on our first date? (This one will surely be helpful when you decide to meet in person)
3. What TV show could you watch over and over without getting tired of?
4. If you could go back in time without changing the past, where would you go, and why?
5. What is the most unusual fear you have?
6. What type of stereotypes are you the sickest of?
7. What do you like most about yourself?
8. What’s your most ridiculous turn-off?
9. What’s the biggest lesson life has taught you?
10. Can you cut relationships with people who are pulling you down?
11. Who do you think has had the biggest impact on the person you are today?
12. Where’s the craziest place you’ve ever hooked up with someone?
13. What’s the worst and best thing about being female?
14. What are three words that make you smile?
15. What’s one thing you would say that makes you distinctive from other people?
16. Do you ever make the first move?
17. What are you most passionate about, and what do you wish you were more passionate about?
18. What is the silliest question you have ever been asked?
19. What makes you feel accomplished?
20. What’s your love language?
Keep in mind that these online dating questions can help you spark fun conversations, but the rest is up to you.
Be honest while answering your online date’s questions, and try to be relaxed. Don’t be uptight like you’re in a job interview because that is a real deal-breaker and it will surely chase them away.
Make jokes, talk about some fun adventures from your own life… because, after all, the most important thing is to make and keep making them smile.