Valentine’s Day can be a challenge. One person is usually super into it, and expecting the world, and the other is desperately trying to not be a total V-Day failure. 

And if you’re still in the early (or early-ish) phases of dating someone, Valentine’s Day can bring undue pressure on the relationship. Let’s be honest, it’s not your fault you two met on January 5th. Why is Feb 14th suddenly a big test of how this thing will be, long term?  

Valentine's GIF from Modern Family

Be a Phil on VDay, not a Claire. (Source: Giphy)

So, to help you either a) avoid awkwardness or b) genuinely get to know the other person better, here are a few great Valentine’s Date questions you two can ask each other:

     ?  If you could snap your fingers and be in a different career (with the same level of success as you are right now), what career would you pick?

     ?  If you could splurge and buy any one thing in the world (no need to be practical here) … What would it be?

     ?  How sure are you that the other person isn't secretly a CIA agent? If you found out that your date was a secret CIA agent, what would your reaction be? 

     ?  Name something about you/your life now that you would never have predicted when you were younger.


    Want more fun questions? Check out our Dating Game. It's got 175 conversation starters and activities – including hilarious rapid fire rounds, thoughtful questions, and wild hypotheticals that’ll help you turn up the 🔥 this Valentine’s Day – and beyond. (And if you're cramming, you can get it in 2 days with Amazon Prime).

    pulling the dating edition out of it's box

    It's perfect if you're one of those people who likes to celebrate Valentine's Day, but doesn't like the pressure of having to come up with interesting conversation. 

    But a couple roses and chocolates isn’t a bad move either, just saying …


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