How to Start a Conversation In Online Dating - Witty Questions to Stand Out

January 22, 2023 Greg Aronoff

5%.

According to recent data, only about 5% of online conversations lead to dates.

That’s - depressing.

So, what can you do about it?

You can boost your chances of meeting your online crush by standing out with your communication. The phrase ‘ice breakers’ might not conjure up the best memories, so view these questions as fun conversation starters that you can use to stand out and be unique.

Open-ended questions that encourage the other person to share more about themselves. For example, instead of asking "What do you do for work?", you could not be like everyone else and ask something unique like What was something you believed as a kid for way too long?”

This allows the other person to give a more in-depth and personal response.

DATING QUESTIONS TO STAND OUT

If you had three wishes, what would they be? (points will assessed on originality, so you gotta come with something a little more than just - 'more wishes')
Describe your own personal style? (and um, if 'mall hair' or 'mullet' are somewhere in the answer... that could be a deal breaker)
Tonight you can do anything you want, no penalties, no reprisals, and the cost is unimportant. What are you going to do? (looking for the magic lamp to answer question one is an acceptable answer)
If you had to name the all-time best song, which would you pick? (remember it's 'all-time' best, so while "Come On Eileen" might be good, we're looking for the number one song here)
Flossing. Before or after brushing?
You’re stranded on a desert island, what three books would you have with you? (books on DIY boats would be clever, but we’re looking for non-survival themed)
If you could have drinks with any historical figure, who would it be and what would you ask them? (This is like a meta Inception question within a question)
I personally like dream boards, what’s on your dream board for the next 1-3 years?
Related, what's something you've always wanted to do (or learn), but haven't - yet?
Talking cringe dates … what’s your cringiest story? (could be yours or a friend’s).
You just invented a time machine - when/where would you go first?
What's the best thing that's happened to you this year?

In conclusion, effective communication is crucial for a successful online dating experience. By using effective conversation starters and icebreakers, users can improve their chances of finding a compatible partner and increase their overall satisfaction with the online dating process.

If you'd like to improve your dating profile description and attract more dates, check out how to get Date Verified and date more often.