20 Questions to Ask Your Crush

20 Questions to Ask Your Crush

Remember the old game 20 Questions? How about Truth or Dare? While these games seem like child’s play, they’re actually VERY interesting when you’re making small talk with your crush. These games can make stilted conversation come to life! They force you both to do away with small talk and start sharing something real about yourselves.

Of course, telling a guy you barely know “Hey let’s play 20 Questions!” might seem a bit uh…juvenile. Instead of structuring these questions as a game, simply bring them up in conversation at the right time. That is, when you’re both alone (or at least the atmosphere is quiet), and when you’re both comfortable with each other. Ask one at a time and not too many at once. Allow him to answer each question at length and then, when he presumably will ask you the same thing, share SOME information while keeping the rest of the story a well-protected secret.

Here are 20 conversation starters for your crush when you find him in a talking mood.

1. What’s the funniest thing you’ve ever seen?

Instantly put him in a positive mood asking him to recall something in his past and relive the funny moment.

2. What was a time you remember when you felt the happiest?

This puts him in touch with his true feelings, comparing what the ideal once was, to what he wants to create with a family in the future.

3. What do you spend most of your free time doing?

This is another question that is somewhat existential. Most people never really think about what hobbies, interests and passions take up their free time. Once they do realize it, they also sense their purpose and what makes them happy on a day to day basis.

4. What is one event or one moment that changed the course of your life?

Great question, as it allows him to think back and reconsider where he was going in life, compared to where he is now. Making him think back shows that you really want to help him find his true calling and find his inner peace. It’s a very attractive proposal and a deep conversation most women simply don’t want to have with him.

5. What’s a statement you read or heard that stuck with you? OR What is your favorite quote?

As much a reflection of his own mind and life as it is trip down memory lane.

6. What is one thing you’ve tried that you would never do again?

Try everything once and fail miserably. But the real joy for a man is in sharing this experience with a woman who wants to know his sketchy past.

7. What’s something about you that your parents would never guess?

This is an important point in the relationship, that is, getting him to confide in you things he could never tell his parents, friends, or other family members. Your aim should be to become the most trusted confidante in all of his circles.

8. Where would you live and what would you do if money wasn’t an issue?

See what’s on his mind and what his future, idyllic vision of heaven on earth really is.

9. What fictional character do you admire / have a crush on?

Sometimes we see ourselves in the fictional characters we like on TV or at the movies. Male figures seem to be people who reflect a man’s own values. Female figures could be the mate he longs for.

10. What advice would you give to your “younger self” from 10-20 years ago?

Another line that makes him think back to the past and his mistakes, but without dwelling too much on the negative.

11. What is true love to ____ (his name)?

Why keep guessing? Get him to tell you what love means to him. Don’t try to change his definition. Instead, take the time to understand what he wants.

12. What was the most embarrassing moment of your life?

Great for a laugh and a sigh of relief that it’s over!

13. What is your favorite _____? (Art, movie, book, TV show, song, etc.)

Answering this gives you a sense of his identity.

14. What’s your oddest deal breaker?

An interesting question, since it dwells on a negative as well as a cautionary sign for your future relationship. But by making it the “oddest” it’s light and funny, not too heavy.

15. What category on Trivial Pursuit could you master?

Let him show off his knowledge of a niche subject!

16. What is your all-time scariest experience?

Scary is not necessarily negative or depressing but more alert and survivalist. Stimulate his emotional memory and relive the experience with him.

17. What was your first impression of me?

Welcome a little honesty to get a sense of how he sees people.

18. If you could change one thing about your life what would it be?

Great way to get him to open up AND set a goal for him to be excited about.

19. What was the worst lie you ever told and did you get caught?

Safe way to broach negativity, by framing it as a learning experience.

20. Who is your biggest crush?

A provocative question to ask him in the beginning. This can be a celebrity or anyone in his life. It lets him know you’re not threatened by other women and enjoy honesty in conversation. More importantly, it gives you insight into what kinds of women or scenarios he finds attractive.

As you can see, these questions are icebreakers with the main intention of helping him to feel comfortable. Once he feels safe enough to share his honest opinions and memories, you’ve really passed a threshold in the friendship. He realizes that he can talk to you about anything! This is the much coveted “emotional connection” he will only get with a few women—the ones smart enough to go for his heart, not just his body.

The lesson is keep things brainy and keep things “real”.

10 Man-Melting Phrases That Make Him Yours

Have you heard of the secret words that unlock a man’s heart and make him addicted to loving you and only you?

They’re called “The Love Frames” and you’ll be BLOWN away by this…

Click here to discover them <<

If you’re ready to have a man…

…fall madly in love with you…

…start treating you like a gentleman should…

…obsessively thinking about you when you’re not around…

…and treating you like the #1 priority in his life…

You have to go discover The Love Frames…

Click here to get them <<

Then just use them on ANY man in your life…

Maybe your boyfriend, husband or fiancée…

Maybe that cute guy you have a crush on…

And watch how he lights up when you’re around…

How he can’t wait to see you again…

How he becomes yours and yours alone…

Click here to discover The Love Frames now <<

You can thank me later!

Talk soon,

Matthew Coast

P.S. You’ll be the first thing he thinks about in the morning…

And the last thing he thinks about before going to bed…

Go here now <<




Leave a Comment

Your email address will not be published. Required fields are marked *