21 Questions You Can Ask to Break the Ice

A game of 21 questions is the easiest way to get to know someone while satisfying your curiosity. Generally, these questions will conclude whether or not you want to date this person. It is a fun way to flirt and shamelessly ask questions that you would be shy asking without playing the game. Plus, it will give you ideas for when there are awkward silences between you two. Here are some questions that can generate a discussion between you and your new squeeze.

1. If you can go anywhere in the world, where would you go?

21 Questions You Can Ask to Break the Ice

This question will allow you to look into your beau’s sensitive side. Travel plans are such a great way to connect on a non-sexual level. It shows character and charisma. This gets you both thinking about planning a potential trip together – which leads to talking about future plans. Not too bad for an innocent question huh?

2. What’s your career path?

Knowing someone’s career path can make or break a relationship. We need to know where you are going in your life to see if things will work out financially. Also, you don’t want to be stuck with someone who is unsure about their life. If they can’t figure out their life then they won’t know what to do with you either.

3. How old are you?

This one is a no brainer, how old are you? If you meet someone out of the blue and they look 27, but is actually 17 – that might be a game changer. Asking for the guy’s age will give you a first impression of how he may act around you and his friends. You don’t want to be the cougar in the relationship if his friends are going to nit pick.

4. What’s your favourite part about a girl?

This can go from super sweet to sexy. When asking a guy this, he may be really honest and say that he likes a huge rack. Or he may turn into a romantic and say that he loves your eyes. Depending on what you want in the relationship, tell him what your favourite part about a guy and the conversation will go on and on.

5. What do you think looks good on me?

Asking a guy what looks good on you would send his imagination going. He would also start thinking about different clothing combinations and even his lingerie preferences. Take notes and surprise him one day!

6. What’s your longest relationship?

Here is an up close look into the skeletons in the closet. See if he is into monogamous relationships or if hes just playing the field.  This also shows if hes even capable to be in the kind of relationship you want. For example, if you don’t want a long term relationship but he does, then maybe this is a no-go.

21 Questions You Can Ask to Break the Ice7. Do you have a sexual preference?

Getting right down and dirty is the way to go. Find out if he’s into the freaky or likes lying there while you do all the work. Know if hes into girls, guys or even both! However, if this is early in the acquaintance then he might hold back until he is comfortable telling you.

8. What’s the most embarrassing thing you’ve ever done?

Who doesn’t love a good story? What he may consider embarrassing may be charming to you. This light conversation starter helps with getting a topic rolling and it will be interesting for both parties.

9. Who’s your celeb crush?

So who does your guy like? JLaw? Beyonce? or some exotic beauty that you’ve never heard of? Celeb crushes are cute but I bet you’ll be dying to know why he likes them. Also, you can come up with reasons as to why you are better than them.

10. What’s your shoe size?

A cute conversation starter that will give him eyebrow twitches. Sexual innuendos are a funny way to get a conversation started on the physical side of the relationship.

11. What’s your biggest turn on, off?

Know what he truly despises and what he loves while getting intimate. Or even how girls act or lack of. Are you the girl that he would ultimately despise?

12. Would you ever go on Fear Factor?

Learn about his adventurous side. Is he willing to eat slugs for a million dollars? How how about covering themselves with cockroaches for a whole 2 minutes? Is he daring enough for ya? It may be interesting what he would do for a million dollars.

13. What’s your best pick up line?

The cheesier the better, this question shows if he has a sense of humor or if he’s always inexperienced in the art of seduction. See if his moves are as smooth as yours.21 Questions You Can Ask to Break the Ice

14. Have you ever been in love?

Try tapping into his past relationships, has he ever been on love? Digging into the past life can show you his views on love and relationships. It may backfire if he does not want to share his past experiences, especially if he’s recently been in a bad breakup.

15. What are your top 3 wishes?

Play genie in a bottle and ask him what his top 3 wishes are. No restrictions here.

16. Have you ever cheated or want to cheat?

Does he have relationship issues? If you are okay with cheating then you can expect him to cheat on you from time to time. However, if you are not then rest assured then you won’t be seeing him again.

17. Describe me in 10 words

Time for him to tap into his creative side. By asking him this, he will need to analyse what he sees in you and decide if he wants to leave a good impression.

18. What super power would you want to have?

Looking back into his childhood dreams will be one of the best ways to get him to talk. Almost every boy idolizes superman or spider man, so what superpower would he have himself? Plus all the little interesting tidbits of his life would give you lots to talk about.

19. Books or TV?

Does he like reading Catcher of the Rye or is he more of a The Vampire Diaries addict? You won’t know unless you ask!

20.What’s your favourite foreplay?

Does he take it slow, or does he like being selfish in bed. A little variety is good but if he’s describing everything you hate in an intimate relationship then don’t be asking for the next date

21. What’s something that makes a girl wifey material?

Have a discussion about what he looks for in a relationship. It tells you if things can work out between the two of you in the early stages of dating. During the honeymoon stage, everything you do will make him happy. However, what is that one attribute that makes him want to be with you forever? Ask him and find out.

21 Questions You Can Ask to Break the Ice

Tell Us…

How many of these questions do you use during a game of 21 questions?

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