Deep Personal Questions To Ask Your Crush

Tell Me About Your Proudest Accomplishment?

Most people like to talk about their proudest accomplishments. This question will boost their ego and help you understand what they view as their biggest success.

Have You Ever Been In Love?

Talking about love is a deep conversation that will help you understand what your crush is like in a relationship, how comfortable they are talking about their emotions, and why they broke up with their significant other. As a personal question, you may want to start this topic after the first date when it is appropriate to ask about their relationship history. If you’ve never been in love yourself, it’s important to be open and honest with communication.

Have You Ever Cheated on Your Significant Other?

This question can reveal a lot about someone’s moral compass and allows you to decide whether you’re willing to risk heartbreak. Change and growth are always possible, so you don’t necessarily need to condemn your crush if they have cheated on a partner in the past.

Which Would You Choose: To Be Smart or Happy?

There is no wrong answer here, but this question will teach you about their view of the world and what they feel is important. Career-driven people may choose to be smart, but those who value experiences and family will choose to be happy.

What Would You Do To Improve Yourself?

Your crush likely has insecurities, and this question is a sneaky way to weed them out. Once you know what they would like to improve, you can help them on their way to becoming their best self. Their response will also show you whether they can be reflective, or whether they are blind to their flaws.

What’s The Sweetest Thing Anyone Has Ever Done For You?

Do you want to know how other people feel about your crush? The sweeter the gesture, the more appreciated they are likely to be.