How To Keep A Conversation Going With A Boy To Get To Know Him Better

By: Samantha Dewitt

Updated November 11, 2020

Medically Reviewed By: Tanya Harell

Getting to know someone better isn't as difficult of a process as some fear it to be. The idea is to keep talking, stay interesting and show that you're interested as well. After all, people tend to like to talk about themselves, and especially if it seems like the other person is actually paying attention to them and what they have to say. So, for those who want to keep a conversation going and want to get to know someone better, it's about following some simple tips and tricks to keep someone going even after they might think the conversation is over.

Ask Open-Ended Questions

Keeping A Conversation Going Can Be Easier Than You Think
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The number one thing to do when you want to get to know someone better is to ask open ended questions. These types of questions mean that the other person can't give a simple 'yes' or 'no.' They need to fill in the question with more context. Questions like 'do you like to read?' are closed questions because a simple 'yes' or 'no' answers it, and there is no discussion. 'What do you think of The Great Gatsby?' is a question that invites the other person to respond and requires them to give a slightly longer answer. Plus, it can lead to a full conversation.

Talk About Something You're Interested In

Focusing the conversation on a topic of interest makes it a lot easier to continue talking. Even if the conversation feels like it is stalling, it's possible to turn the topic over to something that's easier to talk about and simply keep right ongoing. This can draw the other person in by getting them interested. A more palatable topic at least keeps them engaged in current conversation until someone tries out a different topic of conversation to really interest them.

Listen to the Silence

Standing near someone in complete silence can be unnerving for both parties, but letting this happen generally leads to the other person filling in that silence in any way that they can. They don't want to just stand there awkwardly and so they decide to just start talking about something - anything. This can cause the conversation to start back up again even after it's started to wane, or the topics seem to have fizzled out. The other person will come up with something to get things going again. Just wait it out.

'Tell Me More'


This is a technique that can be used if the other person is already talking but the conversation is starting to falter. Asking them to tell them the topic is interesting gets them to continue saying something and makes them feel more confident on the subject. Many times another person may stop talking about a topic for fear of boring the others around them. Asking them for more information says the opposite and can get them really delving into something that they find fascinating or informative.

Ask About Interests

Asking someone what they like to do in their spare time or how they spent their weekend is a good way to get to know them better. This fills in information about hobbies and the way that they have fun. It can be a good conversation starter if there are similarities or it could be a sign that this isn't the way to go. It can definitely get the conversation going, however, because it invites the person to talk about something they are quite familiar with, themselves and their own interests.

Express Yourself

Sharing information is another way to keep a conversation going. Just asking a lot of questions gets somewhat old and the other person is bound to feel like they're on trial or in the hot seat. They're definitely not going to feel comfortable after a while. Volunteering information and sharing similarities will help them feel more at ease and also could invite them to open up even more and share on other subjects or interests where there are similarities or differences. It can make the atmosphere more relaxed, especially if things started getting a little tense.

Pick Up on Cues

There are all kinds of cues that will appear in someone's speech when they first start talking. These can include a lilt to their voice or a tenseness. It could be a tremor or a stutter. Listen to those cues and then pick up on what they want to talk about. Ask them about those things, encourage them to open up and then really listen to what they're saying. This is going to make it easier to start up a conversation, keep it going and then continue to learn more about the other person. It also shows skill in reading their signals and already shows a level of getting to know them better.

Offer Compliments

Keeping A Conversation Going Can Be Easier Than You Think
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Everyone likes to receive a compliment, so giving them out can be a great way for people to want to stick around and talk more. The compliment should be something sweet and not something that sounds creepy or "stalkerish." It could be a compliment about their clothes, their haircut, their smile, their laugh or something else that can be easily noticed from being in the same room or walking up to them. Complimenting someone on their accent or their manners can be a good way to start. These things make a person feel good and more interested in continuing a conversation because they already feel happy to make the acquaintance.

Recent Events

Don't get into things like politics with a stranger. It's generally not a good start. But if there was a weather event recently, or a special event in you gives you an easy starting point to your conversation. After all, the other person has likely noticed and might have something to say. If not, it gives a little bit longer to come up with something that's going to be more interesting and more witty.

Let Them Talk

A lot of guys like to talk about themselves and with a topic and letting them talk is a good way to get to know more about them. It can be much easier and natural for them to talk about themselves, and chances are, they can share a range of information from surface-level facts about themselves to deeper subjects like their childhood, past, or future aspirations. This sharing session may or may not solidify any level of interest in them. In general, it's going to tell plenty and it's going to be a good determining factor of whether this conversation should go any further than the single conversation that it already is.

Tell a Funny Story


Everyone likes to laugh and telling a funny story can get the other person laughing, which makes them want to stick around. A single funny story could be enough to break the ice, and it could be just what's needed to make everyone feel more relaxed and at ease. This could be just the thing to start a conversation on something else entirely, but it shows that both parties are looking for ways to enjoy themselves and are definitely interested in getting to know people better at the same time.

Stay Relaxed

Being too uptight or too tense can give off the wrong vibe. It shows that there's no level of confidence and that's only going to make the other person feel uncomfortable and less confident as well. After all, that body language is going to make an impression on you. Staying relaxed, taking deep breaths and trying to exhibit strength and confidence is definitely going to make a big difference in the overall feeling of the interaction. It's going to make the other person feel more confident and relaxed at the same time as well.

Getting to know someone is definitely going to be a complex process, but you don't need to just stand back and hope that it's going to happen for you. Instead, reach out to someone with any of these techniques. You never know if you might be meeting the one (or missing out on the one). The biggest key is to make sure that you're just open, friendly and welcoming to new people. If you're struggling with these things, then ReGain can help you. It's all about getting to know yourself and working on the skills that you already have to make you feel more confident, approachable and self-assured.

With ReGain you're going to have access to mental health professionals who can help you to better understand yourself and your relationships with others. They can help you to become even more bold and even more confident and, from there, they can help you to improve your life. What's even better about ReGain is that it's an entirely online system to match with mental health professionals. In fact, this service allows you to connect with professionals from anywhere at all, because you're talking to them online. If you have an Internet connection and an Internet-connected device that's all you need, no matter where in the entire country you might decide to go you can still talk to your mental health professional.

Frequently Asked Questions (FAQs) 

What questions to ask to keep a conversation going?

The skill of asking questions is important for one’s social life, including your social life as it pertains to the world of dating. Here are some questions for those wondering how to keep a conversation going to ask:

“What are some of the most important goals you want to achieve during this lifetime?”

“What are your top three favorite music albums?” 

“Who is someone that made a large impact on your life?” 

“Who do you look up to the most?” 

“If you suddenly inherited an abundance of money, what would you do with it?” 

“What TV or movie character do you relate to the most, and why?” 

Keep a few questions like these in mind to ask so that you can avoid moments of awkward silence. When he answers, you can ask any follow-up questions you have to learn more and keep the conversation going.

How do you keep a conversation going with your crush?

As mentioned in the article above, the best way to keep a conversation going with your crush or anyone else is to ask open ended questions. An open ended question is a question that gives room for an answer beyond “yes” or “no.” An example of an open ended question is, “if you could travel anywhere expense-free, where would you go?” 

How do you keep a conversation going during a lockdown?

The coronavirus has definitely changed the dating world, among everything else. Save for the nerves one might experience, going on a date used to be exciting and relatively casual. Now, the common date spots, such as restaurants, are either closed or, at the very least, a much more stressful experience they used to be. Movie theaters are closed as well, and even if they weren’t, social distancing and frequent sanitization are crucial and mandatory at this time. That said, if you’re on lockdown, it doesn’t have to stop you from having an awesome conversation. It can even be your conversation starter, if you choose to make it one. You can start a conversation with the guy you’re interested in by saying, “Hey! How are you doing with the lockdown and all of that? Has your workplace been affected at all?” or “Hey! How are you coping with the lockdown? Are there any particular hobbies or activities getting you through?” Then, you can keep the conversation going by asking follow up questions. For example, if he tells you that he’s been spending his free time during the lockdown on music or a home renovation project, you can ask about it. 

Any time you’re wondering how to keep a conversation going, whether it’s over text or if you’re talking on the phone or in person, one of the most important things to do is to ask questions. People love talking about themselves, and research indicates that asking questions actually makes you more likable. 

How do you flirt over text?

It depends on how obvious you want to be. If you are comfortable making it obvious that you are flirting, you can greet someone by saying, “Hey handsome,” “hey babe,” or “hey gorgeous.” If you want to be more subtle, you can use emoji’s or GIFs and make an effort to keep an engaging conversation going until you’re able to feel out if your feelings for your crush are reciprocal or not. Then, you can step it up a notch. 

How do you flirt on chat?

Flirting on chat is similar to flirting over text. Make an effort to keep an interesting conversation going, and don’t be afraid to compliment the person you’re talking to. Whether it’s, “you are so intelligent,” “you’re so hardworking,” or “you’re literally the most attractive person I’ve ever seen,” a compliment is a great way to flirt via chat. Of course, the speaker and author both have to be engaged to keep the conversation going. If you ask questions and all you get in return is, “okay,” or “I don’t know,” every time, it’ll be hard to keep a conversation going. If you are interested in each other mutually, you should be able to take turns being the initial speaker and author when you talk. What that means is that you should both be reaching out to each other and initiating conversations. A one-sided conversation is hard to maintain, and it certainly isn’t effective when it comes to flirting. If you like someone and, when you think about it, you realize that they are always the person to reach out first, make an effort to do it yourself this time. Even if it’s a simple as, “Hey, I’m thinking about you! How are you doing?” the person on the other side will appreciate it and take it as a sign that you are interested. 

How do I talk to my guy crush?

You can start a conversation with your guy crush the way that you would start a conversation with anyone else. Just add a little bit of extra flair to hint that you’re interested. If you want to be subtle, compliment him and ask engaging questions. If you want to be more openly flirtatious, you can brush his arm, call him handsome, or say something else that gives way to the idea that you like him.

What questions can I ask to my crush?

Asking questions is an excellent way to break awkward silences, on top of being an attractive quality and a positive skill for one’s social life. Here are some questions to ask your crush:  

“What do you want your life to look like in five years?” 

“What are some of the most stand out moments that have happened in your life so far?” 

“If you had to move to another country, which one would you pick and why?” 

“Are there any countries you want to visit one day?” 

“What’s an experience that changed your life forever?” 

How can I impress my crush?

As much as you want to sweep them off their feet, it’s best not to try too hard. Certain traits are known to attract other people and improve one’s social life, so don’t be afraid to play up your most attractive qualities. Positivity, kindness, and thoughtfulness are all attractive qualities to have, for example. Additionally, people love a good listener, so be sure to use active listening skills and do your best to retain what someone tells you to show that you’re really listening. If you remember the small details of a person’s life or what they tell you, it’ll impress them and show them that you care. For example, if your crush tells you about an art project he’s working on, you can make a point to ask, “Hey, how’s that project going?” later on. 

How do you flirt on lockdown?

Flirting while on lockdown is somewhat similar to flirting outside of lockdown. The difference is that it may be much more digital than you’re used to. If you are comfortable using pet names, you can still use those pet names. You can still flirt by complimenting the other person or sweetly asking how they are doing. Now, you have the ability to set up things like video chat dates and use GIFs and emojis via text if you’re at a distance. Those things are becoming more and more normalized as people meet each other on dating apps or want to continue a connection that started in person while social distancing.  

How can I talk romantic?

Speaking romantically is easier than it looks, and it doesn’t have to be over the top. You don’t have to pretend that you’re in a movie or say anything extreme. To speak to someone romantically, compliment them, use cute names like sweetheart, baby, king, or princess if they like them, or reference a famous romantic quote or song. Maybe, you don’t want to send a quote from The Notebook out of nowhere, but if there is a particular romantic quote that makes you think of them, you can say, “oh my gosh, this quote made me think of you” and relay the phrase to them. This is a way to say something very romantic in a way that’s organic and doesn’t feel out of place. The same is true for sending songs or lyrics to someone, which can be a highly romantic thing to do. You can text them and say, “Hey, this song made me think of you.” 

Can you run out of things to talk about?

If you know how to keep a conversation going, you’ll never run out of things to talk about. There are endless questions to ask a person. Even those who have been married for years and years can find new questions to ask their partner. People change, but not only that, we’re always learning about new things, and the world around us is constantly evolving. There are new world events to talk about all of the time, and when someone we know develops a new interest or learns about a new topic, we automatically have a new way to keep a conversation going. There are also random or unexpected questions that you can ask people at any point in time that can start a great conversation. You can ask follow-up questions regarding something that you talked about before, or you might ask a random question such as, “if you could do anything this weekend and money wasn’t an issue, what would you do?” or “if you absolutely had to get a tattoo/get a new tattoo right now, what would you pick?” If you feel awkward asking questions out of the blue, you might even initiate a game of 20 questions. This is a great way to keep a conversation alive, whether you’ve known someone for a few weeks or for years. With creativity and interest on both sides, you can keep a conversation going and get to know the man you’re interested in more and more over time. 

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