What’s your favorite sex toy (hypothetically, or from experience)? What’s the biggest mistake you’ve ever made in bed? How old were you when your parents sat you down for “the talk” and what did they say (or say) about “the birds and the bees”? What’s the biggest dating disappointment you’ve experienced so far? Do you ever catch yourself thinking about doing it with someone of the same sex? What’s the most number of times you’ve ever masturbated within one week? How far would you go to land the guy or girl of your dreams?
One of the ways to test intellectual compatibility is to ask questions.
To ask your boyfriend deep questions means you are essentially seeing how well he keeps up with the important thing.
Whether you’re making conversation at dinner or killing time on a road trip, these questions to ask spark conversations and form connections.
Another reason why the 21 questions game is so great is that it gives you a way to ask questions that are…well…awkward to ask directly.
When was the last time you Netflix and chilled, and then chilled some more…and some more…and some more…Traditional names or made-up ones are all fair game. Be sure to look up the signs and discuss if they’re accurate. Do you want someone like you, or do opposites attract? Or a little from column A and a little from column B? What type of situation would make you close your wallet?
Where a person chooses to live says a lot about them. This question helps you to understand how other people view themselves.
After the 21 questions game have been asked, the person in the hot seat nominates the next person to take their place.
In this version, one person sits in the hot seat, and everyone takes turns asking them questions until they reach 21.
So here is the list of 20 deep questions to ask a guy. However, this is just a basic idea of how you should go ahead with different questions and take them as a conversation starter.