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A Step-by-step Guide On How To Keep A Conversation Going With Someone You Like

Some of the best conversations I’ve had are with total strangers, or people I didn’t know in the start but ended up befriending them because of the conversations we’ve had. Very few people know the knack of initiating and engaging a great conversation. Having a meaningful conversation is NOT small talk. It doesn’t sound anything like this:

Person 1: ‘Sup?

Person 2: Nothing much. ‘Sup?

**Weird silence**

Or perhaps, an indication of how the weather is. A regular rant like,

‘Oh, it’s so hot these days.’

Suggested read: 10 first date conversation rules you NEED to break

I mean, what do you expect the other person to say? The other person will have to nod affirmatively to your previous statement and probably bring out a sad expression on their face.

Then there are those people who respond in monosyllables. The ones that only speak a ‘yes and no’ language. It’s like they have been briefed to ‘answer to the point.’ Some others, who only talk and barely listen. And when they are quiet for a few seconds while you are talking, don’t be fooled. They aren’t listening to you, but are thinking what to say next.

These conversations suck! I hate them!

couple on a date_New_Love_Times

Image source: Shutterstock

You see, I don’t mean to be overly critical, but some people just can’t seem to get it right when it comes to holding a conversation. It’s not their fault, it’s nobody’s fault. It’s just how much they probably like you, or want to talk to you, or hear from you. But you could take charge and steer the conversation to keep things interesting.

I’ve heard a lot of people complain about how ‘blah’ their first date (or a particular date) was, because they probably didn’t know what to say to each other after the first greeting and the perfunctory exchange of pleasantries. Then the awkward silence creeps in, the food and drinks arrive, and it’s over in no time. So, even though you would’ve liked to know the person better, you couldn’t because you both just weren’t able to talk about anything in particular or to keep that conversation going.

So you ask, how to keep a conversation going without hitting a roadblock or reaching a dead end. Here’s how you can do it, the next time you’re on a date.

1. Quick shifts from the pleasantries

You don’t want to waste too much time stating the obvious weather conditions, your frustration over the traffic scene, or silly questions like ‘wassup’. The longer you take to shift away from the initial silly exchange of Q & As, the harder it gets to move onto something concrete. So, you be the first to ask a question that doesn’t involve regular greeting or mundane remarks or that can be answered with a yes or no.

2. Go with your gut

asking a girl out on a date_New_Love_Times

Image source: Google, copyright-free image under Creative Commons License

However much you might deny this fact, within the first few minutes of meeting someone, we have already made assumptions about the other person. Although most times we try hard not to be judgmental, it happens. Which is fine That must roughly tell you what to say next. Use your instincts and throw in a few conversation starters and see how it goes. Start with something generic like sports or world politics, and once you have a fair idea on their views, you could lead them onto other topics that interest both of you.

3. Making mental notes

One of the most important things about keeping a conversation going is that you have to remember what the other person says or thinks. So, make mental notes of some small but important details that they reveal. You will be able to easily impress the other person when you remember these little things.

Suggested read: 16 amazing tips on how to sweet talk a girl

4. Listen intently

A good speaker is also someone who listens carefully. If you are still wondering on how to keep a conversation going, sometimes you simply need to shut up and listen. Give a chance to the other person to open up and talk. This way you will make them feel comfortable and allow them to talk as well. It doesn’t do much to the conversation if all you’re thinking about is what to say next when they’re talking, now is it?

5. Don’t make this about YOU

couple on the stairs_New_Love_Times

Image source: Google, copyright-free image under Creative Commons License

It’s okay to reveal things about yourself to another person on a date. But if you are constantly talking only about yourself, you’d be putting the other person off, very easily. Trust me, no one wants to know about your glitter pen collection or your DVDs on every slasher movie ever made.  Stop making every conversation about yourself. It gets boring real fast. So learn to give a chance for the other person to open up as well.

6. Use other people’s experiences

In my experience, this makes for some amazing conversation openers. So, here you don’t come across as an ignorant person, because you are merely narrating something that you heard from someone else. One thing leads to another, and then you have a full-fledged banter. But one thing to note here is NOT to exaggerate or embellish your retelling. Tell it as you know it, not how you’d like it to have been.

7. Don’t interrupt

Some people have this annoying habit of cutting into someone else’s conversation, sometimes without even apologizing for the interruption. Well, that is really rude, and by doing that, you come across as someone who lacks basic social etiquette. Always wait for the other person to finish their sentence. And even if you did interrupt them, be kind enough to apologize for it and then help them restart their abrupt conversation (which you hijacked!).

8. Ask questions

couple talking_New_Love_Times

Image source: Pinterest

While we want you to encourage the other person to talk some more, ensure that you don’t ask questions whose reply is either a ‘yes’ or ‘no’. In short, ask open-ended questions. Ask questions to prompt the other person to talk a little bit more, reveal their inner self, their true self. This way, you can cut through all the pretentious conversations and talk about some real stuff. So, you ask how to keep a conversation going? We say, ask the right questions!

9. Talk about things you know

Personally, I don’t like it when people talk BS all the time, or when they pretend to be an insufferable know-it-all. Sometimes, it gets uncomfortable when you know very well that the person is just trying to wing it. So it’s better to stick to a known territory. Talk about what you know rather than what you think you know. That way, you don’t come across as a complete douchebag!

10. Be honest

couple talking_New_Love_Times

Image source: Pinterest

If you don’t like something, say it. You don’t have to tailor your opinion as per the other person’s liking. It’s better to be honest and sincere about your thoughts. Save yourself all the unnecessary drama. It’s easier to connect with sincere and honest people than the ones who are wannabes. It’s alright to have an opinion and stick by it; just don’t shove it down someone else’s throat.

11. Add humor

If you have a funny side to you, we suggest you bring that out. Everyone likes to have a good laugh. A good sense of humor is always an advantage; plus it’s attractive. But don’t try too hard, if you are someone who needs to read a book on jokes at night to deliver the same jokes the next day. We suggest you don’t attempt it. But, if you’ve been told earlier that you are funny and you tend to make people laugh often, then don’t shy away. Own your funny side.

Suggested read: Texting tips – Should I text her first to start a conversation?

12. Engage in their interests

Be it music, books, or travel, if you know that the other person has an avid interest in something, it might be a good idea to prod them a little and get them to start talking. Chances are, they are dying to share an anecdote from one of their travels or introduce you to their favorite author’s newest book. That will put them at ease and will keep the conversations moving.

I think that this goes without saying – stay off your cell phone while having face to face conversations with people – whether you’re out on a date or are having dinner with your friends. That is a deal breaker! It’s really sad to see people get addicted to their phones even when they are supposed to be communicating with the people who are physically present around them. A little courtesy never harmed anyone.

Featured image source: Pinterest

Article Name
How To Keep A Conversation Going With Someone You Like
You like this person very much, but you feel as if you just can't hold a conversation with them. Here's how to keep a conversation going successfully!
Steffi D'Souza

Steffi D'Souza

I am a converted dog lover, lipstick addict, and travel enthusiast. I have a distinct love for old architecture and the ocean. I like reading books but love writing more. After experimenting with a gamut of roles in various leading corporations, I have finally discovered my passion. Thus, I have given up my corporate job to pursue a full time career in writing. I hope to write books and I'm already working on my first novel. I blog about all happy things on