We’ve all been there. You’re on a date; you’re ten, fifteen minutes in. Maybe you just ordered your food or drinks. The two of you already have talked about how cool the bar is. Everything is kind of going fine, and then BOOM.
You just don’t know what to say. It doesn’t feel natural. Maybe you force something out.
“So… uh… this wallpaper is cool, right?”
Two days later she responds to your texts half an hour late and has plans already with her friends for the weekend. This is code for: Goodbye forever. You might ask yourself what went wrong, why didn’t she want to hang out with me again? But in the back of your head, you know you could have done better.
You know you could have been more fun. But you tell your friends “It just didn’t feel natural. We didn’t have much in common. I just want to cut through the BS and talk for real.” I know. I’ve been there.
And then it happens again. God forbid it becomes a habit or a belief. “I’m just bad at small talk” or “I’m not a funny guy.”
The good news is that there’s a way out of this. You’re here, and you guessed it; it’s to make her laugh.
Before I start, I want to address a few things. Each girl is different, and each will have her own style of humor. You obviously have your own unique voice and taste in what you think is funny, so, like the Pirate’s “Parlay”, these will be more of guidelines than rules.
To start, some girls will be more serious, and some topics are off limits to joke about. Depending on where you live, who you are with and how well you know the girl, I’m going to leave these rules of discretion up to you. Hopefully, you realize that the traditional “Forbidden conversation topics”, like politics, religion, etc., might be good places not to touch in the beginning.
Two important points before we jump into the tactics:
Most advice out there is crap.
Let me repeat that a different way. A lot of the advice about “how to joke with girls” can be sleazy. People will say things like “give her silly nicknames” or “tease her by stereotyping her”. Maybe this works sometimes, but through the few times that I’ve heard of anyone doing this (especially from the beginning), it either makes most girls weirded out or angry.
Also, you may have heard a lot of girls say “I just want a guy that’s funny and makes me laugh”, but it’s important to recognize the conditions on that statement.
It’s easy to hear something like that and then want to be a comedian. And maybe you’re already hilarious (with your friends)! But are you hilarious to her? In general, being funny and witty obviously helps, but most girls don’t want to be with a clown. Certain types of humour usually do better than others.
Avoid Dad jokes, Rick and Morty humour, and canned lines.
Mindset > Everything
You might know the funniest joke in the world or have the perfect thing to say. But if it’s not coming in a fun tone, you stammer over your words, or you don’t say it with confidence, she’s not going to laugh.
How do you counter this, especially if you’ve always been the serious guy that likes deep conversations and shuns joking around like the plague? With your mindset.
Before you hang out with her, you should reflect on how you want to be, and how you want to make her feel. Most people either waltz into dates and wing it, or spend hours beforehand worrying about how they are going to come off and what the other person is going to be like. Obviously, you would like to be natural and authentic, but it can be of tremendous help to take a couple of minutes to think about how you want to be perceived.
So, if you’re going to be meeting a girl later today or sometime this week, take a minute to think about how you want the interaction to go. Do you want it to be playful? Warm and lighthearted? Fun and curious while you get to know each other more deeply? Stop and think about it, and remember the mood that you want to set, especially right before you hang out with her (and it helps to remind yourself while you’re hanging out as well)
Okay, so now onto some tactics.
Tactic #1 – Inside jokes
Sometimes referred to as “callback humour”. This might take some practice, but it is the easiest way to joke around and connect with the girl we’re with.
The idea is to reference something that you have previously talked about, either in another conversation or earlier in your conversation, in a joking way.
For example, say you were talking about how a tiger escaped from the zoo at some point earlier in the conversation. You leave the restaurant, turn the corner, and you jog ahead to look around the corner making sure it’s safe for her.
“No, there aren’t any tigers around here. It’s safe to go this way,” you say with a smile.
Or maybe she was just telling you how she likes to listen to music and sing in the shower.
Later in the conversation, she asks you what you’re up to the next few days, and you say something like
“I don’t know, but I’m definitely going to try annoying my neighbors by singing in the shower and see how it goes.”
When you reference an earlier part of the conversation it not only makes her laugh, but it also creates a little inside joke between the two of you. Have you ever had any friends who you had inside jokes with? It was like only the two of you know what is going on, right? That’s what this does.
Last note: inside jokes are all about the timing. Try remembering a few things that you talked about earlier in the conversation and wait for the right moment to use callback humor.
Tactic #2 – Exaggerate hypothetical scenarios
Some dating coaches out there say that roleplaying, or pretending to be in an outrageous situation (something that all improv comedians do) can be a great way to make a girl laugh. While I’m not denying that this, if done well, can be a great way to make the conversation more fun, it can often feel unnatural.
If you don’t do it just right, she may not even catch on to the fact that you are making a fake scene. Maybe you tell her that you’re getting married and going on a honeymoon to the Bahamas (or whatever role-play situation someone recommends), and she says “wait… what?”
The worst thing you can do is explain a joke. Something that she’ll understand much more easily but still has the spirit of role-playing is exaggerating hypothetical scenarios.
Think of it like this:
“When I (do something outrageous) then (continuation of the outrageous story)”
“When I become a millionaire then we won’t even have to eat out we can get dressed up fancy and have dinner at my place next time”
“When I start working out more, don’t be freaked out when you turn on your TV and see me on Ninja Warrior”
“When I go to Scotland I’m going to buy a castle. It’s okay, though, I’ll invite you if you want, but you’ll have to cross the crocodile moat.”
It might be easy to think of these now, the trick is to come up with them in the right moment of conversation. If you were planning to go to Scotland, then maybe the Scotland hypothetical situation would work wonderfully.
Also important is to keep the tone playful, and I mean obviously playful. It might be hilarious to your friends to say some of these ridiculous jokes deadpan, but a little enthusiasm and a smile that lets her know that you’re joking can go a long way.
Tactic #3 – Tell Hilarious Stories
This could be an entire guide within itself. Learning how to tell great stories is one of the most important things someone can do on their path to becoming more charismatic and is not a skill that you can really learn overnight.
There are two tricks that most incredible storytellers unconsciously do, though. These are easy to implement, and I guarantee that you will experience immediate results.
When screenwriters pitch movies to producers, the very first thing at the top of the page is the logline.
For a long time, one of my biggest problems was that I was saying the story as it came to me. I didn’t know where I was going with it, or really what I was saying next. They always came out flat, or I missed a punchline. That all changed the day I took a screenwriting class.
Loglines are one-sentence descriptions of movie scripts. They are the first thing producers look at to see if they want to make a movie. How does this help us? Firstly, it gives you the architecture for stories. When you get this down, you will be able to make a fascinating story out of anything. Second, it allows you to control the pacing. By knowing where you are going with the story and it’s final twist ahead of time, you can confidently build it up without having to worry about how to tie it together.
Let’s look at some loglines and break them down.
“The Godfather” Logline
“The ageing patriarch of an organized crime dynasty transfers control of his clandestine empire to his reluctant son.”
Right off the bat, we are hit with the character, “the aging patriarch” and context “of an organized crime dynasty.” Before you tell your story, you want to know who you are telling the story about. Who’s the character, and what’s the context? Is there already a paradox?
Then we go to the action. “(Patriarch) transfers control of his clandestine empire to his reluctant son”. Do you see the inherent tension? How would the reluctant son react?
Let’s look at another one.
“A small time boxer gets a once in a lifetime chance to fight the heavyweight champ in a bout in which he strives to go the distance for his self-respect.”
Again, two characters, two clear motivations, a clear context, and the stage is set.
Now, how do we use taglines to make our stories better? We start seeing stories in terms of taglines. At first, storytelling can seem complicated. But by thinking about the story in terms of a distinct character who has a clear motivation in a context that will result in some tension, we boil it down to the essentials.
So how would this work in real life? Let’s take an example.
Last weekend my friend went to Yosemite National Park, but there was a fire, and he didn’t get to do much hiking. Simple, not super eventful, and even kind of boring, right? Let’s look how I would look at this through the anatomy of a logline.
Character/Motivation: Nature-loving Nick is excited to go to Yosemite for the first time in 10 years!
Context/Tension: He gets there and there is a huge fire, so there is a ton of smoke and you can’t see any of the cool mountains.
Resolution/Twist: To make up for not hiking, he goes skinny dipping in a lake instead, and it’s all okay in the end.
Longines don’t typically include resolutions, but you will want to add one for your story.
Obviously, your story is going to be longer than this, but now that you know the skeleton of your story and what you are trying to do with it, it will be much easier to spice up the character, make the context dramatic, and wrap it all up cleanly to finish it.
Act out Characters
So easy, yet so effective. While the logline is a great way for immediately recognizing key elements of any story, acting out characters is one of the best ways to make a story more engaging and funny.
So what does this look like? When you’re telling your story, and you want to either voice out what someone says or thinks, pause. Make a facial expression that really exaggerates what the person looks like or felt like, and in your best “bad” impersonation (usually the less realistic, the better) of that person’s tone of voice and how they talk.
Impersonations are funny in and of themselves. Many comedians don’t even say jokes, they just do impersonations. In fact, you don’t even have to say anything objectively funny. Just by slowing down and acting out a character in the middle of your story can give it a hilarious context.
Tactic #4 – Tease Her (with tact)
This can easily go horribly wrong so let’s first take a look at what not to do.
As we’ve gone over
Don’t give her a silly nickname
Don’t stereotype her
Don’t mimic or mock her directly
Good teasing is all about your tone, and like most of what we’ve already talked about here: being playful.
With this in mind, let’s take a look at what some of the best teasing looks like.
Reference something you’ve talked about
In light of talking about inside jokes and callback humor, sarcastically referencing something that you have previously talked about in a teasing way can be a great way to get her to laugh.
If earlier in the conversation she told you about how she doesn’t like shrimp, you can tell her that you are going to have a fancy dinner party at your house next Friday and she’ll be invited… but there is only going to be shrimp.
Maybe she told you that she’s afraid of spiders. You can say something like “I was thinking about inviting you over to watch Spiderman, but I don’t think that’s going to work out any more seeing that you’re a scardy-pants for spiders. Oh well.”
Chances are she’ll love this and laugh along.
Another way to tease her is:
Challenge her to a competition
Whether it’s arm wrestling, a race, a board game, or even a dance off, competition is an amazing way to tease a girl and introduce some sarcastic banter. Winner’s get infinite bragging rights (but make sure not to be annoying).
When you introduce the possibility of having a competition, again, make sure it’s fun and non-forceful. Obviously if she doesn’t want to participate, don’t force the matter.
Some tips: make the competition close. Be playful, and maybe lose at arm-wrestling. Go to a bar where you can play her at Connect Four, or see who can name more capitals of all of the states. This should be fun!
Some of the things that we’ve talked about you can start right now. You might even see immediate results if you start doing one or two of these things. I can promise you that even if you do two or three of any of these, your entire vibe around women will change. You’ll become more fun, playful, and attractive.
Other things are going to take more time. Saying the right joke at the right time is a skill that can’t be learned overnight, and making witty introductions, or inventing a hilarious hypothetical scenario might not come to you right away. So what do we do about this?
What I’ve found to be one of the best ways to be consistently funny (and have a great time in general) is to watch standup comedy. What’s really amazing about this is that, if you watch enough, you will slowly start to see the world around you like a comedian does. It’s like direct osmosis – it doesn’t happen overnight, but if you watch enough, you will find yourself cracking more jokes in general.
It’s important to watch comedy that you think is funny. Remember, we want to be authentic. This isn’t about changing your personality or sense of humor. It’s about letting yourself break out of your shell and not being afraid to crack jokes. Some comedians that I really love and resonate with are (old) Dave Chappelle, Hannibal Burress, and Chris D’elia.
Another Tip: This doesn’t start and end on dates! Service people offer some of the best people to practice with because they are nice, the stakes are low, and chances are you won’t ever see them again.
None of this does any good if we don’t do anything. If you’ve read this far and aren’t serious about implementing any of these tips, then it was just more brain food and intellectual stimulation. It’s not actually going to help you.
- If you have any dates coming up, great. If not, friends work just as well for practice. Find the time when you are going to be hanging out or on a date, and write it in your calendar (yes, you need to do this part!)
- Before meeting up, think about how you want the people to feel and how you want the interaction to go. Do you want it to be playful? Fun? Do you want to have a deeper connection? Make that clear to yourself before the event.
- Choose 1 (yes, only 1!) technique that we’ve discussed, and think of five possible variations before meeting up. For example, think of five different stories that you might tell. Now, think of five different characters that you could act out in those stories. Write those down, and visualize what you acting out those characters would look like.
- Enjoy your date! (or hanging out).