How to Never Run Out of Things to Say On a Date So The Conversation Keeps Flowing Easily post image

How to Never Run Out of Things to Say On a Date So The Conversation Keeps Flowing Easily


You’re on a date, everything is going great, but then the conversation just stops and an awkward silence ensues. One of you sheepishly says: “So, anyway…” but you’re just kind of stuck and a painful silence lingers in the air.

You may get inundated with the following questions, either on the date or after:

Should I have said something different?”

“I wonder what he thought about the story I told.”

“I have to keep talking he’s being so quiet this is horrible.”

“What if I made him uncomfortable when I said I don’t like XYZ?”

“What if I scared him away because of that awkward pause?”

“Wait, is it bad if I text him? Was I boring? Did he think I was funny and exciting?”

“Oh man, this is not good. This conversation is actually painfully boring and impossible to continue.”

This is a common experience. Awkward silences can be brutal. We’ve all dealt with an anxiety-inducing awkward silence at one point in our lives. Even worse, they seem to happen more with people we just meet and more so with someone we want to make a good impression on.

Don’t worry… I’m giving you specific strategies you can use so that you never have to worry about running out of things to say on a date.

By the end of the article, you will be able to:

  • Avoid awkward silences
  • Avoid feeling rejected
  • Avoid being worried about how you come off
  • Know what really matters when it comes to being “interesting”
  • Feel calm and comfortable

First, let’s talk about the psychology behind running out of things to say, and the mindset that can sabotage you.

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Awkward Silences

Why do they happen at the worst times? And with people you just met and want to make a good impression on? Running out of things to say on a date is especially horrific. One of my best friends had a date with a guy she had a crush on for months. She was on a dinner date and they ran out of topics to discuss.

She later told me that during the lull in the conversation, she panicked and thought she was blowing it and he would never want to go on another date. I think we’ve all been there!

So why does it happen? Well, the main reason you run out of things to say on a date is you’re trying too hard to impress him. You want to come across a certain way, so you put a ton of pressure on yourself to be funny and charming and witty and sexy and all these things at the same time. That’s a lot to keep up with and trying so hard to be a certain way hinders you from just being yourself. When you let go of the worry and of the trying, then you can be present and things can just flow.

What’s messing you up is the fear of coming across boring or stupid or weird. But these fears aren’t helping you come across any more favorably. They are leading you exactly where you don’t want to be: into the awkward silence zone.

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Don’t Try To Impress. Relax and Just See How Well You Get Along Without Trying.

This mantra will be important for your entire love life; the idea of trying to impress will never serve you and only hurt you.

Your goal is to impress your date, right? Goal oriented thinking means you have an agenda. Having him accept you or reject you creates a win/lose situation. Every word of your conversation is centered around how to get more wins and minimize losses.

You are so caught up in trying to impress him… that you might not have even stopped to examine… “does he impress me?” Don’t mistake this as: “he has to impress me.”

Trying to impress create a vibe that makes it hard to connect. The truth is … a date is about seeing whether you’re on the same wavelength. If you are, you’ll naturally jive. The conversation will feel effortless, natural, and fun. If you don’t jive well (and aren’t on the same wavelength), you won’t have much to say and the conversation will feel forced. You’ll be more concerned about appearing interesting than being interested.

This is a signal that you should listen to: don’t try to force something to work that isn’t naturally working. You are either on the same wavelength or not, and forcing it just causes you waste time on someone who isn’t a good match.

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This is very simple to see when you look at it like this: Throughout your whole life, you’ve probably come into contact with thousands of people… at least hundreds… and how many of those people become your best friend? I’m not saying you weren’t friendly with many of them, but how many became your best friend? Maybe one or two or three? Not all that many.  Were all the rest of those hundreds and hundreds “bad people”? No… they just weren’t on your wavelength and it made sense for them not to be your best friend versus the people who are your best friends.

It wasn’t a problem, it was actually so obvious you probably didn’t think anything of it… and here’s the punchline: Never running out of things to say isn’t a problem when you’re talking to your best friends (because they’re on your wavelength!).

What Should You Do?

What should you do, then, if you’re not trying to impress your date? Go nuts and say crazy things to test him? Sit there waiting for him to liven up the conversation? Act like you aren’t interested in order to appear like you are not trying to impress him, but are actually trying to impress by acting like you are not trying to impress? No, no, no.

This mindset is still self-focused. Being focused only on how you seem to him, and not on connecting with him, is what makes your conversation dull. Being present during your date is the key to clicking. Listening is part of being present. Here’s an example.

You’re on a date with a guy who reveals how hurt he was by something at work. Instead of listening to him, you think, “What can I say to make him think I am supportive and care?” So you come up with something generic to say to make it seem like you care deeply, but what you say doesn’t really hit him because it’s not coming from a genuine place. Constantly strategizing creates an anxious energy within you that doesn’t feel good to be around.  Your mood #1 factor in determining attractiveness. If you’re in an anxious state, he will feel it and won’t feel good about the conversation.

OK, now you are ready for specific conversational strategies!

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Specific Strategies

Now you’re “primed” to take these in since you’re no longer blocked by sabotaging mindsets.

Now that we’ve covered the sabotaging mindsets that are hindering your chances at forming genuine connections, let’s look at some strategies to keep the conversation flowing. The purpose of these strategies is to help get you in the right headspace so you can handle conversations easily and in a way that will allow you to be your true, authentic self.

I’ve compiled the best strategies and tips I know of that will actually work in the real world. This will give you the comfort of knowing you won’t run out of things to say on your next date. This will also allow you to bring out the best version of you. But will not change you.

I’ll give you 5 themes to frame your conversations within that will make both of you comfortable and create a set of factors that foster, rather than kill, a connection.

#1: Create An Excuse to Be Honest (Play Silly Games & Be Silly)

A few examples of silly games are: Truth or truth (you both ask each other personal, out-there questions), never have I ever, etc.

These are mutually agreed upon breaks from “social norms.” You’re giving each other the permission to be honest by setting up a game or conversational activity with rules and guidelines.

You’re basically using silly games to spark raw honesty. Raw honesty is important because it excites the person you’re with.

Don’t be too serious about this, simply suggest some type of, “I ask you something and you ask me something” game that both of you can have fun with.

This way, you don’t have to feel “weird” about being so “real.” You will notice him starting to warm up and speak his mind more often. Once you create this comfort bridge between the two of you, conversation flows more easily.

This is no coincidence. When you shift from being strangers to kind of starting to feel like you’re getting to know someone, you will notice a distinct difference in your own filter. Once you’re comfortable with someone and have an idea of how they respond to things you say, it’s easier to be more and more honest and open.

Conversations are truly interesting when both parties feel safe to share thoughts that they would not be comfortable sharing with most people.

You end up feeling genuinely at ease with this. What you once saw as a problem, a source of anxiety, it is now a natural part of your life.

MORE: The 9 Things The Happiest Couples In The World Talk About

#2: Shift focus from me-centered to him

How do you do this? By being a good listener and asking him questions.

Here is a list of questions for inspiration:

  1. What are your favorite things to do/hobbies?
  2. What are your friends like?
  3. Do you enjoy your job?
  4. What’s your favorite food?
  5. Have you ever been injured before? Like a sprained ankle, broken leg, etc.
  6. Do you have any pets?
  7. Who is your favorite female celebrity? Who is the hottest female celebrity? (asking about a celebrity takes pressure off because you’re talking about someone else.)
  8. What’s your favorite music? What do you like to listen to?

One question deserves special mention because it ties into another point I want to make about the value of analyzing someone …

MORE: How To Keep A Conversation Going With Him

Ask His Astrological Sign!

Yes, astrology can be silly but arguably has some truth. And even if it is total nonsense, guess what? It still serves a functional purpose and is a springboard for more conversation.

Cold Read

Asking his sign allows you to analyze him. You can even Google “Leo male…” and read it to him to see what matches his personality.

People like to hear things about themselves. And if you are reading something a third party wrote on a website it is not like you are the one saying these things about him! So you can always criticize the author for writing something “so ridiculous!” This is a great way to get to know him because you can see what he responds to, what causes him to perk up with familiarity– for example, you read that Leo’s love compliments and he gives a bashful smile that indicates it’s true, now you know one surefire way to get to his heart!

Listen to Him

Genuinely listening is key to being a great conversationalist. Being a good listener might sound simple but it’s not. Why? Because really listening requires you not thinking about how you come off and forces you to quiet your mind, which will always want to dive into the conversation and interject. It takes a lot of restraint to just listen carefully, consider what the other person is saying, wait until they finish and then reply with your thoughts.

MORE: How To Never Run Out Of Things To Talk About

#3: Observe your environment & then relate

You can create an inside joke by observing something atypical in your environment.

How can you do this? Many ways. For example, people watching. See a crazy woman talking to herself? Or a super hot woman who is handing out flyers for her play barefoot? See a couple on a date? You can play a game of trying to “read” them to figure out if it’s the first date or the 10th. If they’re just getting to know each other, or if they’re in a relationship.

Then, once you observe, tie it back to you and him.

“Oh, that reminds me of this time when __”

“This is exactly like that time when ___”

 This creates a shared experience and fosters a connection. It makes a memory.

#4: Bring up pop culture or favorite movies/films/music

You’re creating a safe way to transition into a deeper conversation by analyzing something objective, a third party. A movie can be emotional. A song can make you cry. You begin by mentioning the specific movie or song or whatever it may be (something in pop culture) and then tie it back to your own personal memory and experience. It does not have to be an emotional memory. It can be something funny, too.

“That movie makes me remember ___”

“That song reminds me of the senior prom…”

#5: Frame something awkward as normal (acknowledge don’t ignore)

You can only do this If you are comfortable (hence why you had to learn the stuff before this section could work).

Here is a good example of how to do this. If you’ve seen Pulp Fiction, you might remember this part: Mia brings up awkward silences: “Don’t you hate that? Uncomfortable silences. Why do we feel it’s necessary to yak about BS in order to be comfortable? That’s when you know you’ve found somebody special. When you can just shut the f*** up for a minute and comfortably enjoy the silence.” -Quentin Tarantino, Pulp Fiction

The purpose this serves is to acknowledge the awkward silence. It will automatically calm you down and make you both much more comfortable. So even if you don’t use the Mia reference (this is just an example of how to acknowledge the “awkward” silence), you are making light of it. Do not give the idea of an awkward silence power. Do not allow it to ruin your date.

If a silence ensues, just be comfortable in it. Stay cool and confident, don’t panic and think it means you’re blowing it and this guy will think you’re boring and will never want to see you again. Just be comfortable in the silence. This means you don’t shift uncomfortably, you don’t anxiously check your phone, you just relax, take a sip of your drink, give him a smile, and within a few seconds, one of you will get things rolling again.

What Not to Do:

Now that we’ve discussed strategies you can do, let’s talk about a few things not to do:

  • Do not go in depth into your personal life if it’s on your first date (unless you happen to feel extremely comfortable with him).
  • Do not vent! A date is not a therapy session.
  • Don’t ramble on without pausing to see if he has anything to say

The point of all of these guidelines is to give you a sense of security that will let you be comfortable. If you are comfortable, you will automatically give off a vibe that makes him want to know more about you. He will be genuinely curious and want to see you again.

Want to find out if he’s really losing interest? Click here to take our quick (and shockingly accurate) “Is He Losing Interest” Quiz right now and find out if he’s really losing interest in you…

In summary…

How To Never Run Out of Things To Say On a Date:

  1. Create an “Excuse” To Be Honest (Play Silly Games/Be Silly)
  2. Shift focus from me-centered to focusing on him
  3. Observe your environment & then relate
  4. Bring up pop culture or favorite movies/films/music
  5. Frame something awkward as normal (acknowledge don’t ignore)

never run out of things to say

1 comment… add one

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Tara

This is super helpful, definitely going to try these conversation starters the next time I go on a date, awkward silences are the worst. Thank you!

Reply December 26, 2017, 9:28 am

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