How To Keep A Conversation Going: 6 Tips To Look Like A Natural


There are a lot of great benefits to dating apps. You no longer have to hit the bar or stay out late to meet a cutie. Your dating pool isn’t limited to co-workers, friends of friends, or members of your gym. You also can flirt with a sexy stranger from the comfort of your own home. The only downside? It can be difficult to know how to keep a conversation going over text or IRL. 

There’s nothing worse than chatting with a cutie only to see that they responded to your text with an emoji, which kind of kills the conversation. Well, actually there is something worse: them not responding at all. 

The difficulty of how to keep a conversation going isn’t just over text, it can also be tough in-person to have good banter if you’re nervous or just haven’t figured out your date’s vibe yet. But good conversations lead to second dates, and maybe even to love. So, here’s how to keep a conversation going naturally. 

How to Keep a Conversation Going: 6 Ways to Keep it Flowing 

  1. Be curious and don’t be afraid to ask unique questions

Here’s a fact: pretty much everyone loves talking about themselves. If they act like they don’t, it’s because they’re trying to be polite. So, one surefire way to keep a conversation going is to ask lots of questions. 

While any questions are better than no questions, certain questions spark better conversations than others. If someone has been single and dating for a while, they’ve probably heard most of the basic, small-talk questions a million times by now, so try to go outside the box. 

While you don’t want to offend the other person, ask the questions you’re actually interested in knowing the answers to! Not only will this seem way more natural, but it’ll also show the other person that you’re actually interested in their answers. 

If you’re not sure exactly what you want to know about this person yet, just that you want to get to know them—try upping the ante of the usual questions to make them more open-ended and unique.

For example, instead of asking “what do you do?” ask “what was the best part of your workday today?” Instead of asking how many siblings they have, ask which family member they are closest with and why. Instead of asking what part of the city they live in, ask why they chose that neighborhood!

  1. Chat about mutual interests – and avoid topics that might cause strife

If there was a class on how to keep a conversation going 101, the number one tip would be to find mutual interests. Finding a topic you are both interested in guarantees that there will be more of a natural banter.

Of course, when you don’t know someone, it’s hard to know what you have in common. But, that’s what conversation is for! If you’re meeting someone from a dating app, you might be able to learn about some of their interests from their profile or social media pages if they’ve linked them. You should definitely go through their profiles before date night to ensure you’re armed with some topic ideas. Plus, remembering things from their profile will make the person realize that you do care about their interests, which will lead to a better conversation.

While it may be tempting to bring up current events or politics, you might want to avoid these kinds of topics unless you’re sure of the other person’s viewpoint. You don’t want to get into a debate on a first date – or stop a first date from happening because of a text-message debate! 

Besides, even if you do have the same political viewpoints, politics aren’t sexy. And unless your date works in politics or is an activist, it’s not going to tell you that much about who they really are as a person. 

  1. Focus on listening rather than what you want to say next

Asking questions can only keep a conversation going so well if the person you’re talking to thinks you’re interested in their answers. A key part of how to keep a conversation going is to be just as good of a listener as a conversationalist. 

Try to avoid thinking about what you’re going to say next and instead focus on what the person you’re talking to is saying. If you have trouble with this, try to react to things they say by nodding or making short comments like “wow,” “how cool,” “Interesting,” etc. 

This will not only keep you in the moment, but show your conversation partner that you’re actually paying attention and interested in what they have to say. 

  1. Work in compliments naturally

Just like people love talking about themselves, people love being praised. Of course, if you start a conversation off with a bunch of compliments, it might come off as a bit too much or as a bit inauthentic. 

Instead, work in compliments naturally based on what they’re saying, or based on what you want to learn about them. For example:

  • “I can see that you’re very passionate about what you do, how did you get into the field?”
  • “I love that you’re so knowledgeable about wine! Have you visited any of the wineries around here?” 
  • “Your style is so unique! Even those shoes are unlike anything I’ve ever seen before. Where do you like to shop?” 
  1. Don’t forget body language

While body language might not be relevant for how to keep a conversation going over text-message, it goes a long way in IRL conversations! Here are three ways for showing your date that you’re interested in the conversation: good eye contact, positioning your body to face theirs, and uncrossing your arms. 

Of course, if you notice that the person you’re talking to at the bar is not exhibiting these three body language traits, it might be time to say “nice to meet you” and move on. 

  1. Practice makes perfect

If you find that you’re nervous when it comes to conversations with strangers, find more time to practice! And not just on people that you want to date. Strike up small talk with the cashier at the grocery store, the old man that lives down the hall, or the mom at the dog park. By having conversations with strangers regularly, you’ll become more skilled at how to keep a conversation going with someone who makes you a bit more nervous. 

Approaching conversations as an opportunity to get to know someone new and just enjoying the process will go a long way to help you keep a conversation going like a natural! Good luck out there – you can do it! 

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