Keeping a conversation, talking, and communicating is like art. It has to flow; not to be forced, it can be taught, and each of us has its unique ways to it.
Keeping a conversation going with a guy, especially if he’s your crush, (or if he seems to be the right person you’re dating) can be difficult, and at times overwhelming.
First: let’s accept that it’s ok to feel overwhelmed and not have a clue what to talk about with him, or how to keep a conversation going with him even if it is through text. Second: let’s see what it takes to develop amazing conversational skills.
Here, 15 ways to the secret behind keeping a conversation going with a guy:
1. Use “why, where, how, who, when, what”
“Why, where, how, who, when, what” opens the way to long conversations filled with details about stories between you.
They open up a way to let him be more engaged in the conversation by giving him room to answer more than a yes or no.
- Instead of “Were you happy about it?” use “How did you feel?”
- Replace “That’s a cool hobby” with “That’s a cool hobby, where do you get to practice it?”
- Avoid making questions one after the other.
2. Don’t plan the next thing you’re going to say: listen & be present
When you listen attentively you get a whole more room to ask follow-up questions out of genuine curiosity about the topic he’s talking about. Listen, be there, be present, pay attention, and let him talk.
- Let your thoughts go.
- Don’t plan the next thing to ask or say.
- Let him talk; don’t interrupt him. It’ll impress him.
3. “Tell me something interesting you’ve heard/read/seen recently”
I often use this as a way to break the silence, and people amaze me every time. To make this request you should feel curious to know his reply.
You can ask this one or something else you’re interested in knowing.
- Asking something general can lead to follow-up questions.
- Asking him to tell you something interesting can lead to interesting topics.
- Feel free to ask something else you think would make the conversation less ‘interview-ish’.
4. Ask what a word means if you don’t understand it
It is understandable to not know what a word means or to forget a word for a second. There’s nothing wrong with it.
You can even turn it into something interesting, sort of mock yourself about it, perhaps make a light joke about it.
- Get rid of the fear of being judged just because you don’t know the meaning of a word.
- Not asking about the word when you don’t understand it, can make the conversation slowly die.
- You’ll seem more interesting by expressing curiosity about something you didn’t know before.
5. Ask questions: Questions that can’t be answered with short replies
The questions that can’t be answered with short replies are called open-ended questions. To be more straightforward with it: What questions to ask to keep a conversation going with a guy?
I made a list of less superficial, fun, interesting questions you can ask a guy to keep the conversation going. They’re examples, so feel free to modify them if you feel like it.
Here are a few questions you can ask him (which can lead to follow-up questions like ‘why?’) to keep the conversation going:
- What is it like to be a man?
- Who had the biggest impact on you?
- What’s something you truly love about humanity?
- How would you define ‘bad behavior’?
- What do you do when you’re angry/mad/stressed out?
- What’s something you wish you could talk more about?
- What do you think of the world we’re living in?
- What do you think is something that people mustn’t die without experiencing?
- If you could combine seasons, how would you do it?
- What do you think is the most interesting thing about yourself?
6. Keep eye contact
Some people don’t feel very comfortable with eye contact, and they’d rather listen while looking somewhere else to avoid eye contact. If that’s you, it’s okay. Just make sure you look at him now and then to let him know you’re there and listening.
You can use eye contact as a way to flirt with him too; it can surprisingly lead to fun conversations.
- You’re more in touch with facial expressions.
- Makes you both feel more comfortable in each other’s presence.
- Can remind you or him of something else to say.
7. Tell stories; give details (e.g. childhood stories)
To keep the conversation going with a guy, you have to reciprocate, to share your stories too. When you do so, you want to give details, keep it positive and light.
Giving details will also give him room to comment on something you said, which also helps to keep it going.
- Giving details makes room for questions.
- Sharing stories indicates interest in the conversation and openness.
- Don’t repeat things; it can be off-putting.
8. Talk & listen about: interests, passions, and things you have in common
When he shares an experience, avoid giving a similar one to make his experience equal to yours, instead, listen and watch him light up while he’s talking about things he loves.
Talking about interests, passions, or things you have in common makes room for follow-up questions, the conversation to move on further organically while you change topics without noticing it.
The next thing you know is 3 hours passed by without even noticing it.
- Conversations about interests and passions are longer because they’re things you/they love and ‘there’s just so much to talk about it.
- Talking about things you have in common helps the conversation move, and the topics can change organically (without trying).
- Be open to listening and learning about something you’re not interested in doing (e.g football).
9. Don’t approve everything with nodding or saying ‘yes’
If you’re interested in whatever he’s telling you, you will nod or you’ll say yes, but you’ll do so without noticing yourself, or without forcing yourself to do so.
If you’re not agreeing with something, say it. It makes the conversation keep going while you share your opposite ideas on the topic with him.
- You don’t have to avoid nodding or saying ‘yes’ at all costs. It’s ok to do it now and then.
- Don’t hesitate to share your opinion, once they express theirs, on a certain topic.
- Feel free to express an opinion that’s not the same as theirs, even if it is disagreeing.
10. “There’s this thing I do…”
Sharing something you do usually that makes you happy, or when you’re bored, or angry, or sad, will make him also share an opinion of his or even better, something he does when he’s in the same situation.
For example, let’s say you see something that reminds you of your ‘thing’; You can say “There’s this thing I do when I go alone to grab a bite…” to then continue it with “I got reminded by that/this”.
- When there’s silence, take the moment to share something interesting you usually do.
- Sharing something interesting you do, gives them room to ask questions.
- Sharing particular things from your side makes conversations longer.
11. Express your opinions and speak your mind out
When he likes you, he’ll like you more when you’re expressing your thoughts and opinions (i.e. speaking your mind out); it helps a lot in keeping the conversation going.
Be authentic, don’t be afraid to speak your mind, even if it is something that may come off as completely out of the blue, say it. Speak confidently, and don’t hesitate.
- When you speak, speak with confidence.
- Be authentic, say what you mean.
- Enjoy yourself, make jokes if you’re good at them.
12. Avoid bad-mouthing other people
If you want to keep a conversation going with a guy/boy/man, you want to keep it interesting. A good idea to achieve that is to avoid bad-mouthing others; It lowers the quality of the conversation.
- Bad-mouthing others will not lead to a quality conversation.
- Express your opinion on a person/behavior without being judgemental.
- Try to add quality to your conversation to keep it going.
13. Be open to the possibility of him surprising you, without having an expectation based on your perception
He knows something you don’t, for sure! Be open to the possibility of him surprising you with something about him.
You might get an initial impression of him, or you might already have an idea of who he is, but still be open to being surprised by him.
You’ll be more curious that way, and the questions will naturally flow, without you trying to force them just for the sake of keeping the conversation going.
- Be open to new ideas, opinions.
- Don’t judge him based on what you ‘know for his type’.
- Try to give him room to impress you, through curiosity and listening.
14. Go with the flow, even if it leads to silence
Silence isn’t necessarily a bad thing. I believe it is better than trying to force the conversation to go further on. Don’t try to force the conversation, nor the silence to go away, it’s normal, it happens.
- Don’t force the conversation in a certain direction.
- Try to accept that silence is not a bad thing.
- He might eventually make his attempt to break the silence, so be patient.
15. Give him a specific compliment
If you genuinely like something about him, or something about him impressed you, then feel free to comment on it: a compliment. He’ll perhaps start talking about it, and the conversation will go on, and who knows where it’ll lead later…
- You can comment on something you appreciate about him.
- Compliment him if something in particular about him impresses you.
- Don’t compliment him just to get a compliment back.
What to talk about with a guy? – Topics to talk about when the silence kicked in
When you’ve got no clue on what to talk about with a guy, think of these topics:
1. Things you have in common.
Talking about things you have in common makes you both more talkative, makes you both feel more connected to one another. There’ll be this sense of understanding, hearing, and seeing each other.
2. Childhood memories.
Childhood memories are never a bad idea. Even if one or both of you didn’t have good memories, talking about it will build a connection between you, and it’ll help you to grow closer with one another.
3. Passions, interests, hobbies.
People light up and shine when they talk about things they love. And I love watching, hearing, and seeing them do so! Do that, talk about passions, interests, hobbies. Talk about what makes you happy.
4. Ask him questions on things he mentions often.
Perhaps he mentions football, or tennis, or his mom, or skiing, anything really, ask him. Even if it is something like “I noticed you talk a lot about your mom. How do you feel about your connection with her?”, go for it.
5. Talk about friendships.
Friendships at times can lead to sensitive stories, however, you can know a lot more about each other by the way that you talk about this topic, the things you share about it.
6. Talk about movies/songs/books.
This never fails you! Movies, songs, and books are pretty good topics to talk about with a guy.
Considering that men have slightly different tastes in movies, books, and songs compared to women, this could lead to an interesting and beautiful discussion.
7. Talk about family.
Talking about the family with a guy will show a lot about what you stand for, how your personalities developed, how your relationship with your families affected your personalities, and so on; Besides that it’s interesting, this topic also helps to build a connection between you two by sharing stories and experiences.
8. Things that remind you of something at the moment.
Let’s say you’re drowning in silence, you see something, it reminds you of something else, take the chance to talk about it. An example:
“Oh, this reminds me of this little doll I had when I was a kid…”
9. Your first impressions of one another.
Talking about your very first impressions of one another often leads to funny conversations or super romantic ones; Talk about it, and find out.
A simple “Wait, what was your first impression of me when you saw me for the first time?” will do.
Wrap up: Keeping a conversation going with a guy
Keep it going easily, and don’t try to force the conversation to not go silent, or to go in a specific direction. Let it flow organically. Ask questions when you’re curious, listen to him when he’s talking. You’ll be good, trust me.
Love,
Callisto
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