21 Questions to Ask a Guy You Like: Questions Game (Video)

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Going out of a first date? Want to get to know a guy you just met?

Asking the right questions earlier will help you quickly find out if a guy is a keeper or just a waste of time. To help you evaluate your new potential boo, I have created this list of 21 questions to ask a guy you like (a.k.a. the 21 question game).

Make sure to ask your guy every last question.  Don’t skip any of them.  Never go on a second date before asking these 21 questions first!  You have been warned!

One important thing to note. You should be prepared to answer all the questions you plan to ask. Your guy friend may want to know the same information about you. That, or he may try to deflect questions he doesn’t want to answer by firing them back at you. 🙂

21 Questions to Ask a Guy You Like – The 21 Question Game21 questions to ask a guy you like - question game 2


1. So… do you currently have a wife or girlfriend?

Yes, this question is very forward, and possibly a little off-putting. However, it’s the most important question to ask guy you are interested in dating. You don’t want to waist time or risk heartbreak with a guy that has strings attached.

Sure, he can give you a dishonest answer. While his words may say “no”, what does his eyes and his facial expression say? Does he further the point and say something like, “I stopped dating my last girlfriend six months ago”. Or does he simple say “no”, and politely waits for the topic to change? 🙂

At minimum, you can hold his answer against him if you discover later that he was lying.

If he says he’s about to divorce his wife or break up with his girlfriend, put him on hold until he has officially left those situations.

2. Do you have any baby mommas I have to worry about?

A man that has kids is not automatically an issue. You’ll want to make sure that he is taking care of them financially. If he’s already a dead beat dad, what type of father will he be to your kids?

You also want to make sure he is apart of his kids lives. It’s easy to simply send money (especially if the government takes it directly from his paycheck!). Make sure your boo is taking care of his little ones on an emotional level, not just the financial.

Lastly, you want to be aware of the existence of any ratchet baby mommas, or too many baby mommas. If his one baby momma is crazy, you have to decide if you want to deal with that drama. If the guy you are interested in has three baby mommas, you might need to consider if you want to potentially become lucky number four.

3. When did you graduate high school?

This question can lead to all sorts of good information. Here are some of the important pieces of info to extract from this question and a few good follow up questions:

  • Determine if he actually graduated from high school. It’s not a given!
  • Since most kids graduate high school around the age of 18, you can use the year he graduated to estimate how old he is (or, you can just ask him his age. lol).
  • If he doesn’t volunteer this information, ask him if he went on to college.
  • Follow up questions: Ask him if he was a jock, class president, or leader of the chess club.

21 questions to ask a guy you like - question game 3

4. What do you do for a living?

Your new boo must be employed, be in school, be rich, or have a very good reason for not being any of the above. If he isn’t in school and he’s not working, he needs to tell you what he does all day long. Wrong answers included “hangs out with unemployed friends” and “plays Call of Duty”.

5. What’s your family like?

The goal here is to find out if he has a family, and if the family life is stable. If he deflects questions about his family or deflects discussions related to meeting his family, this could be a red flag.

6. What were you like as a kid?

Was he a bully? Was he a momma’s boy? Did he experience some life changing event that will inform you about his personality or well being? These are all good things to know!

7. What are your friends like?

If he has successful friends, he probably is or will be successful himself. Likewise, if his friends are unemployed, uneducated, incarcerated, or otherwise thuggish, then run away. Run far, far away.

8. What do you do for fun?

Hopefully his answer include things that you also find to be fun. Since you are going to be dating this guy, you will want to know what your weeknights and weekend will be like. If all he says is “Netflix and chill”, that could be a problem. LOL

21 questions to ask a guy you like - question game 4

9. Which do you prefer? A woman with good looks or a woman with intelligence?

The correct answer is “both”. Be careful with this question as his answer may indicate how he feels about you- are you good looking, intelligent, or both?

10. Where is your favorite place to hang out?

This question serves a couple of purposes. First, you genuinely want to know what types of activities he likes to engage in. Second, when he says he’s too busy to hang out with you, you will know where he’s likely to be hanging out with his friends (or his other boo).

11. If I met your ex, what would be the first thing she’d say about you?

You probably won’t get an honest answer. However, it may be useful to see his reaction. Perhaps it will indicate whether he was the dumper or the dumpee? Was he the player or did he get played?

12. What type of music do you listen to?

You have to throw some softball questions into the mix so that he doesn’t feel like he’s being interrogated. Afterward, resume the interrogation! Besides that, it may be a good sign if he has an extensive Barry White CD collection.

13. Do you know how to dance?

Some say that if a man is a good dancer, he’s probably a good lay.  Don’t take his word for it, however. Get him on to a dance floor and find out for sure.

14. Do you play any sports?

Hopefully your boo lives an active and fit lifestyle. If he’s in college and plays a sport there, find out if he’s headed to the pros! Nothing wrong with dating a real baller!

If the guy is a little on the chubby side, you probably know the truthful answer to this question. Perhaps you can then use this question to work in a discussion about joining a gym together. 🙂

15. What’s your favorite place to go on vacation?

This is another dual purpose question. One, you want to find out if the guy has actually traveled. Two, this is your opportunity to share with him where you would like to go next. This way, he can start saving up for the trip!

21 questions to ask a guy you like - question game 7

16. Can we connect to each other on Facebook, Twitter, and Instagram?

Definitely get access to his Facebook, Twitter, and Instagram. A treasure trove of information can be found in these social media accounts. Pay special attention to any women constantly commenting on, liking, or retweeting his posts.

Check out those picture galleries as well. Guys are often not clever enough to clean up any past incriminating images before connecting online with a new boo.

17. What’s your favorite video game?

More importantly, does he play video games at all and if so, how often? Does he occasionally play Madden Football or is he a level 100 World of Warcraft player? If you don’t want to spend your weekends watching him increase his experience points, this is a good question to ask.

18. Can you cook?

This is a great question if you don’t know how to cook yourself.  If you are going to eventually live with this man, you need to know how both you are going to eat.

19. What is it about you that makes you the ideal boyfriend?

The answers to this question varies. Hopefully his answer includes such things as honest, loyalty, trustworthiness, caring- basically, the usual lies.

20. What do you look for in a woman?

Hopefully his answer includes traits and characteristics that you have. Otherwise, he just told you that you are not the one.

21 questions to ask a guy you like - question game 6

21. If I went to your place this evening, would it be tidy?

The honest answer is probably “No”. The nice thing about asking this question is that it will likely cause him to clean up his place before you visit.

Be careful about asking a guy about his place, however. The question may suggestion to him that you plan to visit his place soon. 😉

Need more than 21 questions to ask a guy you like?

Check out the video below for some additional questions to ask a guy.

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