50+ (Fun & Flirty!) Valentine’s Day Questions for 2023

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Valentine’s Day 2023 will soon be upon us. (For better or for worse!) But what are some of the best Valentine’s Day questions to ask? What Valentine’s Day conversation starters are there? And how can you craft your Valentine’s Day conversations in a different and interesting direction?!

Well, my friends, whether you’re single, dating or in a relationship – here’s 50+ fun & flirty Valentine’s Day questions you can use this year.

50+ Fun & Flirty Valentine’s Day Questions

So let’s get stuck straight in, shall we? Here’s our all-time favourite Valentine’s Day questions, broken down by category.

Uh huh, Valentines Day chat doesn’t have to be dull. Make the most of the “season” and really get into it, for interesting, different and creative conversation starters.

Valentine’s Day Questions For Singles

First up then, we have our Valentine’s Day questions for singles.

These are conversation starters you can have with your friends or family, around the topic of Valentine’s Day as a whole. 

So maybe you’re asking your single friends, or maybe you’re single yourself.

You can even still ask these Valentine’s Day questions if you’re in a relationship as – well – they are pretty interesting. So have a read and see what “takes your fancy!”

1) What do you think are the best things and worst things about Valentines Day? (As a whole.)

2) What do you personally like the most and least about Valentine’s Day? 

3) How do you feel going into Valentine’s Day this year?

(E.G. Maybe they’ve usually always dreaded Valentine’s Day, but this year – they feel totally okay about it, having reached the point of being happily single and single by choice. This is something to acknowledge and celebrate for sure!)

Questions about Valentines Day

Let’s Keep Them Coming…

4) Have you ever heard of Galentine’s Day? And how do you think we can make THAT a bigger thing?!

5) How big of a thing do you think Valentines Day is anyway? How many people do you think properly celebrate it? Both those who are and aren’t single? And why? / Why not?

6) What do you think is the best way to celebrate Valentine’s Day when you’re single?

7) How do you think the majority of singles feel about Valentine’s Day? Do you think it’s something that most are aware of / think about / feel pressure over? Or not so much?

8) How are you spending your Valentine’s Day this year? And – if you could do anything on Valentine’s Day – how would you most like to spend it?!

9) If you were able to play Cupid on yourself – what kind of person would you match yourself with?! And… HOW would you match the two of you together? (Let’s dream about fairytale love stories… But JUST for today! 😛 )

10) Do you have a crush you could declare your love to this Valentine’s Day?! And would you?! If so – how? (Let’s brainstorm ideas!)

Valentine’s Day Questions When Dating

Next up, we’ve got some Valentine’s Day questions you can ask on a date.

These are kind of similar to the Valentine’s Day questions for couples, but they’re softer and more suitable for anyone on a date, at any stage.

Have you only met the girl / guy that night?! It doesn’t matter! Have you both specifically come out for a date on Valentine’s Day? Then even better!

See, we’ve added some flirty questions in here, because hey – isn’t it all about getting sparks flying?! You may as well have fun with it! So let’s get stuck in…

11) How do you feel about the “big day” coming up then?!

This is a great dating app question, best asked with 0 explanation. When they then reply “huh?!” You can say, “Well Valentines Day… of course! 🤪”

Don’t use it as an opening line (until they get your jokes / banter) but it’s great to throw in with someone you maybe would like to go on a date with, this Valentine’s Day.

12) So, did you picture seeing me, sat opposite you, on Valentine’s Day?! 😉

[If you’re out on a date on the day itself.]

13) Got any rom-coms you binge watch this time of the year then? And hey… don’t worry, I won’t judge! 😉

Don’t forget – flirting by teasing is a great flirting technique when done properly! You can also tie this into a more “out there” question of – “fancy some company?!”

Things to talk about on a date

Let’s Keep Them Coming…

14) So, what’s the most romantic thing you’ve EVER done? (Either on Valentine’s Day or just in general!)

15) What would be your idea of the PERFECT Valentine’s Day date? (And yes, you can get rid of the crowds that often come on Valentine’s Day. This is your “dream” Valentine’s Day we’re talking about here, after all. 🤪)

16) Do you like Valentine’s Day? Are you a romantic kind of person? What’s your thoughts on it all as a whole?

17) So, some say that Valentine’s Day is just a way for stores to make more money?! Do you agree? Disagree?! I meant we can’t deny that it does add billions into the economy. So, let’s discuss!

18) What’s your FUNNIEST Valentine’s Day story (to date)?! After all, they say laughter is the way to your heart, right?! 😉

(Note: This could be a Valentine’s Day story from when they were single, or a funny disastrous date, or even funny that they saw happen to other people on Valentine’s Day.

It doesn’t have to be about their ex… Although if they use it as a chance to reminisce about their ex, it could be a sign they’re not over them!)

19) What would be your idea of the WORST date you could possibly go on?! ESPECIALLY on Valentine’s Day?

20) So Valentine’s Day is all about sharing your “love” for another person. Do you find it difficult or easy to express how you feel?

Challenge: Give me your most heartfelt declaration of love speech. (As if you were in a movie! Now’s your time to shine! 🤪)

Valentines Day Questions For Couples

Moving on now, here’s some of the best Valentine’s Day questions for couples to ask each other.

Uh huh, conversation NEVER has to run dry – no matter how long you’ve been together. It’s just about getting a little more creative with your conversation-starters… And what better time than this Valentine’s Day?!

See some questions to ask about Valentines Day, include…

21) Is Valentine’s Day the most romantic day of the year? If not, what day is? Or was day do you think is the most romantic day of the year for us?

E.G. Maybe you go all out to make anniversaries super special. Or perhaps you have your own significant date (like a “Meetversary” for instance!)

This Valentine’s Day question may also lead into…

22) How can we make Valentine’s Day more romantic, special and memorable this year?!

23) Does Valentine’s Day make you feel more loved & appreciated? Why / why not?

If you’ve not previously spoken about your love language, now’s a good time to get clear on this too. (That’s always an interesting one!)

24) What would be one thing I could do this Valentine’s Day which would TOTALLY surprise you?! (In either a good or a bad way… But let’s try to focus on good ;P) 

25) What’s one thing you would (secretly or not!) love me to do this Valentine’s Day? (No holding back!)

Valentines Day Conversation Starters

Let’s Keep Them Coming…

26) What’s the cutest Valentine’s Day story you’ve ever heard?

(From family or friends for example? Not just a “fairytale movie scene!” We want to be able to feel the love and genuinely believe in it, too!)

27) What would be your idea of the BEST Valentine’s date and the WORST Valentine’s date? And what are some of the best and worst ones we’ve had so far?!

28) If you were to change some things about Valentine’s Day, what would you change?

(This is an interesting one, and probably something they’ve never thought about before. Maybe they’d take out the gift giving or bring back the letter-writing. Either way – it will be fun finding out!)

29) Build a picture in my head of THE MOST romantic Valentine’s Day gesture / celebrations you can POSSIBLY think of! Let’s see who can come up with the most romantic thing!

30) How do you think couples can better keep the romance alive in every day life? Not just on Valentine’s Day?

Would You Rather Valentine’s Day Questions

“Would You Rather” Valentine’s Day questions are also always pretty fun, so it would be rude NOT to include some of these in here, right?! 😉

The great thing with these are they’re fast paced, and open up the funniest conversations! So why not throw out there, the question of…

Would You Rather…

31) Create a love potion or use Cupid’s bow and arrows to spread the love?

32) Have a hand-made Valentine’s Day card (made with lots of love and thought of course!) or a huge, fancy, shop bought one?!

33) Receive 100 roses or receive 100 mini chocolates?

34) Confess your love to your crush on Valentine’s Day, or never know how they feel about you?!

35) Be proposed to in front of a huge crowd of people or alone in a room full of candles?

Romantic date topics

Would You Rather…

36) Attempt to do the Dirty Dancing lift or the final dance in Step-Up?

37) Fall in love at first sight or fall in love over years of friendship?

38) Receive a mailbox full of love letters or be serenaded with an original song?

39) Kiss 100 frogs to find true love, or forget the frogs & run the risk of never finding it at all?!

40) Be a matchmaker or have a matchmaker match you with the perfect person?

Valentine’s Day Trivia Questions

Looking for some fun facts about Valentine’s Day to throw into conversation?

Some – actually interesting – Valentine’s Day trivia questions that you can memorise for the “season”? Then here’s our 10 favourites to finish!

41) How many cards are gifted or sent on Valentine’s Day each year in the US?

Answer: 145 million. [Source]

42) Which type of person receives the most Valentine’s Day cards? (This answer may surprise you!)

Answer: Teachers! [Source]

43) The Goddess of love, Venus, is believed to have been born from what?

Answer: Sea foam! (Uh huh, it’s not actually butterflies and rainbows after all!) [Source]

44) How many wedding proposals are made on Valentine’s Day each year?

Answer: It’s said to be over a million! Love is in the air! [Source]

45) Where is Valentine’s Day “reversed” in the fact that women traditionally buy chocolates for men (as opposed to men “wooing” women?)

Answer: Japan! [Source]

Valentines Day Trivia

Let’s Keep Them Coming…

46) In how many countries is Valentine’s Day an official holiday?

Answer: Surprisingly (or not!): none! But it’s still vastly celebrated! [Source]

Although: In 496 A.D., Pope Gelasius I made the feast of St. Valentine an official holiday, apparently hoping to expel the pagan rituals of Lupercalia by combining it with St. Valentine’s Day. However, after the Second Vatican Council in 1969, Pope Paul VI decided to remove St. Valentine’s Day from the calendar of major holidays & it’s remained that way ever since!

47) The heart is a popular symbol used on Valentine’s Day. How did it get its shape?

Answer: There are several theories surrounding how the heart symbol came to be. One states that the heart symbol is based off the seedpod of silphium, an ancient plant believed to help with conception, love, and sex.

Another theory states artist and scientists in the Middle Ages attempted to draw the heart the way it was described by ancient scholars, and the drawing stuck. [Source]

48) What did women used to believe would bring good luck on Valentine’s Day?

Answer: Bay leaves! In the 1700s, 5 bay leaves under their pillow was said to bring sweet dreams about their future husbands. [Source]

49) To which bridge do lovers go in Paris to put a padlock symbolising their love?

Answer: Pont des Arts (primarily!) [Source]

50) Last but not least – how long was the longest marriage recorded?

Answer: 86 years 290 days. Amazing huh?! #CoupleGoals [Source]

That’s All For This One

So there we have it – 50 fun, flirty or just simply entertaining, Valentine’s Day questions to ask.

I hope this has filled you with inspiration for different conversations you can have, around a set theme!

Good luck. Wishing you all the very best this Valentine’s Day!


Valentines Day Questions
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Ella Stearn
Ell is a Breakup, Dating & Relationship Specialist & Coach, with over 3 million annual readers, globally. As the Creator of Forgetting Fairytales, her mission is to help you learn to love yourself, find the right person to give your love to, then make it a love that truly lasts.

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