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

By Samantha Dewitt

Updated March 03, 2020

Reviewer 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

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The number one thing to do is . 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'

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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 telling 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

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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

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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.


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