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7 Ways to Keep a Conversation Going on a Date

The Seven Best Tips for Keeping up Conversation While Dating

When it comes to dating, one of the biggest problems people seem to run into is a lack of conversation. That awkward moment where all the hot air you’d previously been billowing over this potential love interest just evaporates.

You think you’ve got something new to say and… tumbleweed.

It’s a fear many guys have and inspires many a question to dating experts the world over such as:

  • What If I run out of things to say?
  • What if there’s an awkward silence?
  • What if I say something and she just replies with one-word answers?

Instead of living in fear of what may happen, instead embrace the joy of what can happen, when armed with the right way to handle any conversation. After you’ve finished this article, you’ll be able to keep a conversation flowing for hours, without missing a beat.

Let’s get started.

1. If You’re Nervous, Don’t Be Afraid to Admit It

There’s something about men that makes us want to seem macho and not afraid of anything. The truth is, admitting you’re a little nervous about the date can help to build some common bonds between you are your date immediately.

A lot of people feel nervous on the first date, so it’s not an unusual thing to admit. It’s also an excellent ice-breaker. Being honest is important and letting your date know where you’re at can take off some of the pressure. Just make sure to focus the conversation on getting to know each other.

2. Ask Open Questions, and Listen to the Answers

Knowing the difference between closed and open questions is an important tool in the arsenal of any conversationalist. What’s the difference?

A closed question is: ‘Do you like living in New York? ‘
Answer: Yes

An open question is: ‘What do you like about living in New York?’
Answer: One of my favorite things about living in New York is no-two days are different.

Open questions give you a much better chance of opening up the conversation. Learning how to use open-questions is one of the best skills you can learn in a lead-up to a date and can keep the conversation flowing for hours.

You can follow up one open question with another open question based on their answer. Based on the answer above you can ask another open question, ‘What has been one of your favorite days in New York?’.

This type of question asking can lead to some really deep stories being shared and you can learn a lot more about a person from these type of questions, while also having them driving the conversation forward.

3. Avoid Politics or Religion

You’d think this would be obvious but in any social situation with new people, bringing up a conversation where you have an opposing view can leave the other person devaluing what you say, it’s probably best leaving those conversations at the door.

Instead of talking about religion, you can talk about faith. Instead of politics, you can talk about community. Just do yourself a favor and don’t bring these up in conversation.

4. Don’t Lie

Bending the truth, white lies, and even outright lying shouldn’t have any place on your first date or any for that matter. Starting off your relationship with a lie, even a small one, can have disastrous knock-on effects.

When people want to be liked they often embellish truths or hide data that is relevant to make themselves seem more authentic. As you continue to date though, the truth will come out.

5. Ask About Their Job Not How Much They Make

One of the biggest conversation killers can often be based on peoples jobs. Some people don’t like to talk about their job, some people don’t want to share how much they earn, and other people just want to pry and find out if this relationship is going to worth pursuing based on a monetary salary. Those should be alarm bells if you get that lost option by the way.

Instead of asking about how much somebody earns or talking about how much you earn, talk instead about what you find rewarding from your work, or ask the same question to your date. Talking about the parts of your job that you love and talking from a place of passion often leads to more thoughtful conversation.

6. Don’t Talk Negatively About Yourself

When it comes to talking about yourself, beating yourself up or making jokes at your own expense is one of the most self-destructive pieces of behavior you can have as a person. Talking badly about yourself shows the person you are speaking to you don’t respect yourself, so why should they respect you?

Remember that modesty is appealing; low self-esteem is repelling. Instead of focusing on your flaws, remember to be positive and it’s better to say nothing at all instead of something self-degrading.

Telling somebody you’re bad at dating, for example, is akin to a director telling everyone going into his movie that it’s terrible before they’ve even seen it.

While on the subject of talking, try to remember not to do too much talking as well. Talking too much about yourself is another big turn off.

Remember that everybody loves talking about themselves, and give your date that opportunity, don’t hog the limelight.

7. Do Your Homework

With the world of online dating and Facebook at your fingertips, it’s easy to be able to do some research before a date. Imagine in the 90’s ringing up a date’s friend and trying to find out things like her interests, where she works and what she does on the weekends. It’d be outright creepy.

In 2018 however, we all happily share that information for free online. If your date has added you on Facebook, take a look at her profile and try and pick up a few conversation points.

The same can be done with a Tinder profile, understand their bio and their pictures and ask thoughtful questions about these in dates.

Make Awkward Pauses A Thing Of The Past

With these seven tips, you should be armed with all of the tools you need to make sure you never get into the conversational no-mans-land again. For more advice on the best ways up your dating game, check out some of my other posts.

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About Jamie Atkinson Jamie Atkinson is a freelance writer and sales coach who has over 10 years of experience coaching, selling and training in the field. He was born in the UK but now travels all over the world, teaching other aspiring entrepreneurs how to achieve their own success by sharing the benefits of having a lifestyle business. You can find out more from Jamie over at

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