15 Personal Questions To Ask During 20 Questions, For When Things Get Steamy

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, which is where classic games like 20 Questions come in. As silly as the game may seem, it gets the job done. It can 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 bae, 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 bae warm up to the direction where you're trying to take the conversation. That way, they're not blindsided when you drop, "What's your sexual fantasy?" So next time you and bae are 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 15 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 you 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?

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 your bae seemed open to answering them, full speed ahead with these slightly more personal ones. If they were hesitant, it may be best to give them a bit more time before you dive in.

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?

Deeply Personal

These next five questions are best reserved for when you and bae 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 feel ready, and you can suss out that bae is ready and feeling into it, 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.

3. Have you ever cheated or been cheated on?

4. What's your favorite sex position?

5. What's your biggest sexual fantasy?

Next time you feel the conversation lulling out, and you want more, try one of these 15 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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