How to Get to Know Your Boyfriend Better

Last Updated: September 2, 2022 References

When you’re in a relationship with a guy you like, you might start to realize that you don’t know him as well as you’d like to. Your boyfriend could be a tough guy to read or perhaps you’re new to the relationship and looking to learn more. Whatever your situation, you can learn more about your boyfriend by having a conversation, observing him in different situations, and interacting with him with friends and family.

Method 1

Method 1 of 3:

Having a Conversation

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Pick a calm, quiet moment. In order to truly focus on getting to know your boyfriend better, pick the right setting to have a deep conversation. Avoid a noisy bar or restaurant or talking at a time when one of you will be busy. Instead, choose to have a nice talk while on a walk through the park, during a picnic, or while sitting out on the porch looking at the stars.^{[1]
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Expert Source

Connell Barrett
Dating Coach
Expert Interview. 24 September 2019.}
- Choose a place that you both feel comfortable in. For example, if you both like the forest, you could go on a hike.
- Even if you both may like to hang out in noisy environments, they are not a good choice because they'll make it hard to each one another.
2
Ask about his childhood. To get to know your boyfriend fully, first find out how his earliest years were. Ask him where he grew up, about his siblings, his relationships with his parents, and his friends when he was a kid. Ask him his favorite memory and his worst memory from his childhood. ^{[2]
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- This will help you get a general feel for the major events that occurred while he was growing up. It may even help you understand some of his quirks.
- Be prepared for him to ask things about your childhood in return!
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3
Talk about work or school. Ask your beau questions about the schools he’s been to, his experiences there, and his current job. Find out if he enjoys his job or if he wants to change careers or go back to school.^{[3]
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- Ask him what his ideal job or college would look like.
- You might say something like “So, tell me about your job now. What do you like best about it? And what do you wish you could change?”
4
Discuss both of your dreams and aspirations.^{[4]
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Expert Source

Connell Barrett
Dating Coach
Expert Interview. 24 September 2019.} Share with your boyfriend your goals and wishes in life, and encourage him to do the same. When you open up to him, chances are he will feel comfortable enough to open up to you. Be sincere and vulnerable about what you want out of life, and take his dreams seriously, regardless of what they may be.
- For example, find out if he wants to further his education, join the military, or travel overseas.
5
Ask about his favorite books, movies, and music. You can also really get to know a person by finding out what kind of entertainment they enjoy. You might even find out that you have more in common than you thought. Find out what books he enjoyed most or could read over and over. See if any films have made him cry. Find out what concerts he’s been to or ones he’d like to go to.^{[5]
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- You can try saying “When I was a kid, I remember reading To Kill a Mockingbird and it really changed my life. Do you have any books that affected you like that?”
6
Be a good listener. During this process, be sure that you are fully engaged in the conversation. You cannot get to know someone if you are not paying attention to them. Put your phone down and truly listen. Laugh with him, cry with him, kiss him, and nod to show that you are paying attention.^{[6]
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- Pay attention to the nonverbal cues he gives as well, such as smiling, frowning, or fidgeting.
- Respect his privacy if he doesn’t want to talk about certain topics.
- Use follow up questions to gently dig deeper, once you know that he feels comfortable talking about a particular topic (e.g., Say, “Really? Tell me more.”).
7
Talk about yourself, too. In getting to know him, be sure that he is getting to know you, too. As he finishes sharing stories or information about himself, share some things about you, as well.^{[7]
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Expert Source

Connell Barrett
Dating Coach
Expert Interview. 24 September 2019.} This will help the two of you grow closer.^{[8]
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- For example, when talking about his childhood, you can also talk about your own. If he recalls a time he got in a fight with his sister, you can say “I used to fight with my brother all the time, too! Mom and Dad were always grounding us that.”
8
Respect silence. You can get to know someone even when you are not speaking. Notice how often you are silent with your boyfriend and if that silence is comfortable. This is a sign of true closeness. Allow for moments of silence when you don’t have anything to say and simply enjoy the peace in the room.

Method 2

Method 2 of 3:

Observing Him in New Environments

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Try an adventurous activity. Getting to know your man should go beyond just the conversations that you have with him. Get to know with him by seeing how he responds to stress, fear, or excitement. Visit a local theme park together, go horseback riding, or try something like indoor skydiving. Notice how he reacts to these types of situations.^{[9]
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- For example, if he gets on a rollercoaster, and then gets very anxious or frustrated, this could indicate that he's not a person who handles fear well.
- He might also react to an adventure positively and the two of you may have a lot of fun.
2
Try a new type of food. Expand both of your culinary palettes by trying a food you’ve both never had. Whether you head to the new restaurant downtown or you cook a meal together, this will show you how your boyfriend responds to new experiences.
- He might not like the food very much, which is fine, as long as he's honest about it. On the other hand, complaining repeatedly about the food isn't a good sign either.
- If he doesn't like the food you chose, let him choose the food next time!
3
Start a new hobby together. Try something new together like dancing, horseback riding or painting. Notice how he reacts to learning something new. Some people will give up if they can’t get the hang of it soon and others will keep at it until they master it.^{[10]
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- Notice how your boyfriend responds in situations where he is a rookie. Does he get frustrated and give up? Or does he laugh at his mistakes and try to have fun?
4
Play a game together. Some people are sore losers and others take losing or winning like a champ. Play some video games or board games with your boyfriend and see how he reacts to the outcome. He might have a competitive spirit that matches yours or perhaps he sulks when he loses or is cocky when he wins. Either way, this will help you assess his character.
- You can also do something that is a team effort like a puzzle, escape room or even a DIY project. See if he leads, follows, doesn’t help at all, or takes over completely.
5
Notice how he treats others. In getting to know your boyfriend better, pay close attention to how he treats and talks about others. This is a good indicator of how he might treat you to your face or behind your back. For example:
- Does he gossip or speak badly about friends? If so, he might speak badly about you, as well.
- Is he kind to waiters when you're out to eat or is he rude to them? An ideal partner is one who treats all people well, regardless of their social status.

Method 3

Method 3 of 3:

Meeting Friends and Family

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Pay attention to his family interactions. If you have met his family, think back on how their interactions were. If you have not met them, perhaps he has spoken to them on the phone while you were around. If he is kind and loving with them, then you likely have a good man on your hands. However, if he is harsh, be careful.^{[11]
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- Before you judge, learn some of his history with his family. For instance, if they've been abusive or neglectful in the past, this could explain why he is cold to them.
2
Get your family’s opinion. If you're serious about this boyfriend, plan some time for him to meet your family. Bring him over for Sunday dinner or invite him to go to a family event with you. Notice how he interacts with your family, if he's friendly, reserved, or rude. Ask your family what they thought of him later, but take their opinion with a grain of salt. For example:
- If your family did not like him because of his race, religion, or social status, you can disregard what they say. These things should not matter.
- If your family did not like him because he seemed manipulative, then you might want to ask them more questions as this could hurt you in the long run.
3
Plan an outing with your friends. In addition to learning more about your boyfriend, allow your friends to do so, as well. They will often pick up on things that you might not notice. Go out to dinner with him and some of your friends or out bowling. Ask them what they thought of him soon after.
- For instance, your boyfriend might've done something nice for your friend while you were in the restroom that they'll want to tell you about.
4
Meet his friends. It is said that you are the compilation of the five people you spend the most time around, and it is likely that your boyfriend spends a lot of time with his friends. Get to know those closest to him and get a feel for their character and personality. Though many friends are different from one another, they will likely have many similarities.^{[12]
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- As a bonus, they will also likely tell you some embarrassing stories about your boyfriend!

Expert Q&A

Question

What can I do to get to know my boyfriend well?

Connell Barrett
Dating Coach
Connell Barrett is a Relationship Expert and the Founder and Executive Coach of Dating Transformation in New York City. Connell has over five years of experience as an international coach who helps men connect with women by unlocking their best, true, most confident selves. He is the author of the Amazon bestseller “Dating Sucks but You Don’t,” and has appeared on Good Morning America, the "Today" show, Access Hollywood, and in Best Life, Cosmopolitan, and The Oprah Magazine. In 2019 he was named Datezie.com's “New York City’s Best Male Dating Coach."

Connell Barrett

Dating Coach

Expert Answer

Try to find a quiet place to have your conversation and ask questions about him. Be sure you also respond with things from your own life so he can know you better too.
Question

What if I'm always busy and never get to see him?

Community Answer

Find time, and if its really impossible, then try talking online. Just make sure to let him know you care.
Question

What if I don't have a boyfriend? How do I get one?

Community Answer

This article may be of some use: how to get a boyfriend. Something else to consider is prayerfully journaling about the attributes you really value in the man you'd eventually like to marry. Doing so helps you to create a vision for the kind of man you want in your life, so you won't settle for just anyone. Then get out there and do the things you enjoy and keep your eyes peeled. You can't (and shouldn't) just wait around for a boyfriend. It'll happen in due time...Get on with the business of living!