This woman is playing 20 Questions by asking her crush personal questions.
These 30 Personal Questions Will Take Your Flirting To A New Level

Because 20 questions just aren’t enough.

by Christy Piña
Originally Published: 

Getting to know everything and anything there is to know about a new person is one of the most fun parts of the beginning stages of a relationship. You're looking for any and all reason to talk to this new special someone, and it feels like a round of 20 Questions is the only way in. As silly as the 20 Questions game may seem, it gets the job done. With all those personal questions thrown in the mix, things go from zero to 100 real quick. From "What's your favorite color?" to "Have you ever had a threesome?" — the possibilities are endless, and that's what makes it so fun. If you're looking for personal questions to ask during 20 Questions that can go past the basics and help you get to know all the dirty details about your new love, look no further.

As eager as you may be to learn all you can about them as quickly as possible, when it comes to asking personal questions about their past, it may be best to start with something on the lighter side. Starting with lightly personal questions and working your way up to the deeper, more personal ones can help your new boo warm up to the direction you're trying to take the conversation in. That way, they're not blindsided when you drop the highly personal question, "What's your sexual fantasy?"

So next time you’re playing 20 Questions and you're tired of the same surface-level asks you tend to gravitate toward, kick it up a notch and consider trying one of these 30 personal inquiries instead.

Lightly Personal Questions

Trust me, I know how tempting it is to want to jump right into the dirty deets. But starting small can help the conversation build up, and it might make them feel more comfortable opening up about the more serious things in their past. So, as hard as it may be to start with some of these less personal questions, it may lead to a more in-depth conversation later on down the line.

1. Who was your first crush?

2. When was your first kiss?

3. What attracts you to people?

4. What's the most embarrassing thing you've done to get someone's attention?

5. Are you looking for a relationship?

6. What’s your greatest relationship strength?

7. What do you think is the cutest thing about you?

8. Who’s your celebrity crush?

9. What’s your dream date activity?

10. What’s your funniest rejection story?

Mid-Level Personal

Once you've started the conversation off with some lightly personal questions, your partner may be open to giving you more information about their past romances. Try to feel out the conversation when you ask the less personal questions first. If they seem open to answering them, then you can go full speed ahead with these slightly more personal ones. If they were hesitant, it may be best to hold off.

1. Tell me about your first love.

2. What about your first heartbreak?

3. Is there something you've ever kept from a partner?

4. Do you have any regrets from your past relationships?

5. Do you get jealous easily?

6. Would you ever want to get married to someone?

7. What’s your favorite thing about starting a new relationship with someone?

8. How did you get over your last bad breakup?

9. How did your parents’ relationship impact your view of love?

10. What’s one thing you wish you could tell your ex right now?

Deeply Personal

These next 10 questions are best reserved for when you two are starting to get significantly more comfortable with each other. You're open to talking about things you maybe haven't talked about in a long time, and they are, too. At this point, hopefully you feel comfortable dipping your toes in the ~dirty~ side. If you both feel ready, ask them these deeply personal questions.

1. Have you ever had a threesome? Would you ever want to?

2. Tell me about your first time having sex.

3. Have you ever cheated or been cheated on?

4. What's your favorite sex position?

5. What's your biggest sexual fantasy or kink?

6. When did you start masturbating?

7. What’s your most surprising sexual fantasy or kink?

8. What’s your favorite body part to kiss?

9. Have you ever regretted having sex with someone?

10. What’s the sexiest thing someone could say to you right now?

Next time you feel the conversation has hit a lull, try one of these 30 questions. Take advantage of the "newness" of the relationship and the fact that you're still learning all there is to know about them. But most importantly, be respectful. No one ever has to answer anything they don't want to, including you. If you sense that the person you're texting is uncomfortable, don't press. But if they're eager to answer your questions and to learn more about you, carry on and enjoy this exciting new time. It can truly be one of the most exciting parts of a new relationship.

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