If you want to get to know a guy you like, the best way is to talk to him. If you are shy or don’t know them well, it can be difficult to have a long conversation. If you are having a conversation and he seems uninterested or if the conversation is starting to fizzle, it is up to you to put some life back into the conversation so that it will last longer. There are questions to keep a conversation going with a guy that will allow you to get to know them better. These questions could also help him get to know you better as well.

 

Open-Ended Questions

If you want to keep the conversation going, you should ask open-ended questions. If you ask questions that require a simple yes or no answer, your crush will feel like he is being quizzed rather than getting to know you. Questions that require long answers will keep the conversation going.
• What kind of movies do you like? This question will help you learn the type of movies that he likes, and it can open up a conversation about that movie if you saw it as well. You can talk about your favorite and least favorite parts and your favorite characters.

• What do you do for work? Even if you already know what your crush does for a living, this question will help you find out more about what he does all day. You can ask him details about his job, and what he likes and doesn’t like about it.

• What do you like to do on your days off? Your crush can give you a few answers to this question, which will keep the conversation going. It will also give you a chance to see what he does in his free time, giving you some date ideas if things begin to progress.

• What is a typical night like after work? This question will give you an idea of what your crush does after work. When you know what he is doing, you will know the good and bad times to call or text.

• What is your favorite book? This is a great question because it can be the start of a long conversation and a good debate. You can find out what he likes the most about his favorite book and what makes it his favorite in the first place. If you read the book, you can have a long conversation about it. If you haven’t read the book, you can read it and save the talk for later.

Questions About Past Relationships

These questions may be difficult for you because you have to listen to your crush talk about his ex-girlfriends. As much as you may hate to hear about the ex’s, it is best you hear about everything now so that you know what to expect.
• When was your last relationship? This is an excellent question to ask. It may not spark the longest conversation, but it will give you an idea of where his head is. If his last relationship ended a few days or weeks ago, he might not be ready to jump into something serious. If it had been months since he was with a girl, he could be ready to settle down.

• How did your last relationship end? You might not want to hear about your crush’s ex, but this question is important. It will let you figure out where he is emotionally. If his ex cheated on him or was physically abusive, he will have baggage, which can be a lot to deal with. This question can keep the conversation going, especially if he asks about your last relationship.

• Are you looking for something serious? This question will let you know if you are wasting your time. If he says he isn’t ready for something serious, you will know where you stand. You can also ask him why he isn’t ready or why he thinks he is, which will keep the conversation going.

Questions About Him

People love to talk about themselves; it is human nature. When you ask your crush questions about himself, he will love to answer the questions, often with long answers that can spark an ongoing conversation.
• What is the craziest thing you have ever done? This is a fun question that your crush will love to answer. It will lead to a long conversation while he tells you the details of his crazy adventure. It will also let you know if he has an adventurous side.

• What was your childhood like? This will let you know how your crush was raised. This question can open up a conversation about his childhood home, his parents, and siblings. It can also give him a chance to tell stories about his childhood, which can be a long conversation.

• What were you like in school? This question will tell you a bit about your crush when he was younger, and it will give him a chance to tell you stories about him when he was in school.

Questions About the Future

These are great questions to ask because most of the questions will begin a long conversation. It will also help you figure out if you have similar goals. If not, you can stop wasting your time.
• Where do you see yourself in five years? This question will help you find out where your crush sees himself in the future and if you have similar goals. This is a very important question to ask, and it can lead to a long discussion.

• Are you happy with your job? This isn’t a yes or no question, which is what you are looking for. If he is happy where they are, you can find out why and what makes the job so special. If he isn’t happy, you can find out what he would rather be doing and if he plans to make the necessary changes to get into the field of his choice.

• Do you believe in marriage? Some guys don’t believe in marriage, and some are too young or immature to know. When you ask this question, you can find out if he wants to get married one day, and if not, why he is against marriage. This will let you know if a relationship with him will be a dead-end relationship.

• Do you want children someday? This is a good question to ask early because if your thoughts on children are different, that likely won’t change. When you find out early, you won’t waste your time on something that will never work. If he does want children in the future, you can discuss his idea of the right time and the type of parent he plans to be.

Fun, Flirty Questions

When asking your crush questions, you don’t want every question to be serious. Asking fun, flirty questions will make the conversation more enjoyable, and it will let him see that you have a fun side.
• What is the craziest place you ever had sex? This is a flirty question that will bring sex into the conversation. He can tell you his crazy story, which opens the door for you to tell yours. This will let him see that you know how to have fun and be adventurous.

• If we went on a date, where would we go? This question will show your crush that you want to be more than just friends. It could also open up the door for him to ask you on a date.

• Are you the type to have sex on the first date? This question will let your crush know that you have sex on your mind when you think of him. It will also give you a chance to let him know how you feel about sex on a first date to prevent awkwardness if you end up going out.

Final Thoughts

The key to getting to know your crush really well is to ask questions. You don’t want to ask simple year or no questions. These types of questions won’t lead to an ongoing conversation, which is necessary if you are going to learn a lot about him.

You also don’t want to fire off question after question. This will make him feel like he’s on a game show or taking an oral test. You want your questions to lead to an ongoing conversation, so there will be no need to quiz him with question after question.

Also, make sure that you mix some fun and light questions in with the more serious ones. If everything you ask is serious and requires a lot of thought, it will take all of the fun out of the conversation.

If you feel uncomfortable asking question after question, you can make the questions a game. You can tell your crush that every day, you can ask each other one question. This is a fun way to ask your crush the questions you want the answers to, and it will be fun rather than overbearing. It will also give your crush a chance to learn more about you.