Say Goodbye to Awkward Dates with These Improv Tips

Try these improv dating skills when you go out on your next date.

I used to dread going on first dates because they all felt the same to me — mostly small talk about the weather, work, and a cursory review of places you’ve lived and traveled. Blah, blah, blah. So many of my first dates have felt anything but substantive, and eventually dating stopped being fun.

Then I realized: if dating isn’t fun, I’m doing it wrong.

The “dating” label adds pressure for some reason, and that needs to change. “Dating” is simply meeting someone new, doing a fun or new activity together, and living in that moment. 

Once I took the pressure off dating, I realized just how fun it could be! And when I combined it with elements of my improv training, my “Getting-Asked-Out-On-A-Second-Date Ratio” went way up — just sayin’.

Just as there are certain “moves” an improviser can implement to make any scene more interesting and fun to watch, you can apply similar “moves” to your dating life experiences meeting new people.


I mean, like, *really listen.* I know your date may have super dreamy eyes and you might catch yourself not focusing on what he’s saying because his eyes are so dreamy… are those gold flecks in his brown eyes? Or is it the lighting? … Sorry, what was that you said about how you once went sledding with penguins in Patagonia? You don’t want to miss the story about the penguins! Focus up! 

In improv, we constantly practice responding to the very last thing that was said, which means you have to listen to that thing. If your date is talking about penguins and then you say “So, how ‘bout them Cowboys?!” he will most likely feel dismissed and not want to go out with you again. 

A good listener is one of the top qualities that people look for in a partner, so demonstrate that you care about what the person has to say. Good eye contact and building on what your date is saying will show that you’re listening. If you’ve never been sledding in your life, now is a great opportunity to bring it up: “Wow, I’ve never even been sledding with humans, much less penguins!” Now we’re talking about how/where you grew up, and we’re off to the races.

Have a point of view

Something that makes comedy particularly great is when the comedian makes bold statements about things you wouldn’t expect anyone to care about. “I really hate curtains you can see through. What’s the point?!?”  

Watching two people in an improv scene connect deeply around their love of seahorses is silly and fun. Conflict in such low-stakes positions is actually interesting, not divisive. By contrast, two people tiptoeing around how they feel about the weather is lukewarm, uninteresting, and forgettable. If there’s a TV show you hate to love, or a book that got under your skin, or a pet peeve that’s unique to you, share it!  State your opinions boldly, and enjoy the fun that comes with a flirty debate.

Focus on the people in the scene

I love talking about my nieces and nephew more than anything in the world. And if you get me going, I will talk about them and show you pictures of them for no less than 90 minutes straight. BUT, on an early-stage date with someone, it is important to focus your energy on the two of you together, because that’s what matters most at that point in time. Plus, that’s what living in the present feels like: being in this moment with this person, talking and laughing and losing all track of time. 

Imagine watching any scene with two people talking exclusively about someone who is not in the scene — and you never see or hear from that person ever. So boring! So anticlimactic! So pointless! You and your date are the people in the scene. Focus on the important stuff: YOU (plural)! 

Know each other

This one might sound strange, given you could be on a date with someone you’ve never met, but hear me out. In improv, one of the most important things the actors do is assume there is already some kind of relationship between the two people on stage. This allows the freedom to make it matter — to ask interesting questions, to be vulnerable, to take some bigger risks with your scene partner. 

Imagine a scene with a doctor delivering some odd news to a patient: “I’m sorry, you’re going to lose your kneecaps in three to four weeks, and there’s no known cure.” Now imagine the patient has been going to this same doctor for his whole life — what other diagnoses has this doctor dished out over the years? Or, is this a doctor who has been a spectacular medical provider, so this diagnosis is superbly confounding to the patient and violates his trust? From here, we can start to uncover the history of this dynamic, which is fun and interesting to watch on stage.

The same can be true on a date — assume your partner is there because they want this encounter to matter, even if it’s just for the one evening. Take on the disposition of someone who can ask good questions, flirt a little more, have meaningful conversations, and connect deeply. 

It’s not compelling for two people to talk about their golf swings, but it’s riveting to witness a healthy dose of witty banter on the golf course that leads to a fast proclamation of love on the seventh hole (I don’t recommend this IRL, but you get the picture). So mention the weather early to get it out of the way and move on to the meaty, important topics. Like kneecaps, and why you need them.

Add information (aka: Yes, And)

On stage, it is critical that you are contributing to the scene in some way — whether that’s via direct dialogue, pretending to be a washing machine, or creepily spying on the scene through the window. As an audience member watching a scene, I want to know the motivation of all members of the scene. I want to know why this mother brought her 7-year-old kid to sewing club just as much as I want to know what the 7-year-old thinks about being at sewing club (needles everywhere!) — and why that person is creepily spying through the window. All people deserve time and space to explain why they are there.

One of my biggest pet peeves during the early stages of dating was when the man I was with wouldn’t ask me any questions about myself. I used to understand this as his lack of interest in my opinions, thoughts, and beliefs, but it usually came down to him just not being that good at asking questions! Since then, I now add information to the conversation without being prompted directly. 

While dating, it is as important to reveal aspects of your personality / interests / desires as it is to get to know those aspects of your dating partner. Remember that dating isn’t an interview — you want the other person to walk away feeling good about your time together, and knowing a lot about you, too!

Play a character

I’m kidding, definitely don’t do this. Be 100% yourself!!

Have fun! 

In the early stages of dating, it is so important to remember to keep things fun — after all, meeting new people is fun! Additionally, it can be tempting to forego the interesting conversations for the easier, lighter subjects because it’s safe — those topics don’t reveal too much about who you are. In reality, though, what we are all truly seeking is genuine connection, which necessarily involves listening, revealing information about yourself, and staying present in the moment. 

One of the best pieces of advice I got about dating was: “You’re not looking for the ONE HUNDRED, you’re looking for the ONE.” You won’t click with everyone you go out with — and that’s okay. It’s still fun to learn about what makes another human tick, and when you do really click with someone you’ll be able to keep the spark aflame. 

Have fun. Be vulnerable, open, honest, and true to yourself. And break a (proverbial) leg!

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