The best resource on social and dating anxiety is an obscure book by a clinical psychologist from Australia you’ve never heard of.
It’s called Dating Without Fear by Dr. Thomas Smithyman. There’s a chapter titled “Make a Mediocre Impression.”
The idea behind the chapter is this: we often put too much pressure on ourselves to be clever when we start conversations with new people. Especially people we’re attracted to.
We think we have to be like friggin’ Ryan Gosling in “Crazy, Stupid, Love”––with off-the-cuff, bold, perfectly flirtatious, witty banter.
It’s an insane standard to measure against.
In fact, clever “lines” like this are actually selfish when you first meet someone. It creates a performative expectation that’s hard for you and the other person to keep up with.
From Dr. Smithyman’s book: “Starting a conversation with somebody is not a complicated performance piece.”
Instead, Dr. Smithyman’s advice is that we should focus on making a mediocre first impression.
Why?
Because when we try to make a good first impression, the pressure is so great that we never say anything at all.
At least a mediocre impression is an impression.
The best way to do this is by having a bunch of boring, predictable, even repeatable conversations with a ton of people.
And since it can be hard to come up with things to say in the moment (especially if talking to strangers is new for you) it helps to have a framework.
This is my framework for creating conversation go-tos that I use repeatedly in the park, the gym, the yoga studio, the grocery store, and elsewhere, that have helped me build my social and dating life.
The PUA Stuff Is Whack
Leave cleverness to the movies.
I think a fulfilling social life is the cumulative result of starting the same boring conversations with as many people as possible.
This is not about creating “openers” as the Pick-Up Artists called them. These fedora-wearing sociopaths would develop conversational gambits they could employ like incantations to manipulate vulnerable women.
God, I screwed myself up so badly in my early 20s reading that nonsense.
This guy is named Mystery and he is the foremost Pick-Up Artist expert in “openers” (yes, I’m dead serious).
It took me a long time to realize the truth: walking up to an attractive woman (or anybody for that matter) and saying the right thing is a fool’s errand.
Saying ANYTHING is what matters.
In his book, Dr. Smithyman tells the story of one of his friends who says “sorry” to random people to break the ice. If he’s in someone’s way or interrupts what they’re doing, he simply apologizes to spark a conversation.
This is why small talk about the weather is such a common trope—it works because it’s easy.
A cliché like "Do you come here often?" can be an effective icebreaker because it provides an easy entrance into conversation.
Even so, it can be useful to have some easy-to-remember conversation starters you go to again and again.
That’s why I have a few go-to conversation I repeat all the time.
Here’s the formula I use—each conversation starter is:
Place-dependent
Boring
Repeatable
Neutral/unsexy
Provides an easy entrance and exit for both people
To create your own go-to conversation starters, steal some of my frameworks:
How I Start Conversations at the Yoga Studio
Before Class
If my mat is next to someone I’ve never met before, I might turn to them and say:
“Have you ever taken [teacher’s name]’s class before?”
They might say, “No” and turn away, which is my cue to end the conversation. No harm done.
Or they might say, “No” with engaged body language or say, “I haven’t. Have you?”
Then, because I’m a regular at most of my favorite teachers’ classes, I get to look cool because I can fill them in on the teacher’s style, and even recommend similar teachers.
Or they might say, “Yes, I have taken [teacher’s name]’s class before.” In which case we can launch a mini-investigation into how and why we’ve never met each other before.
After Class
“How do you feel after class?”
I ask this question to everyone after class. My mat neighbors. People at the cubbies. The teacher. Everyone.
It’s great because the answer actually tells you a lot about a person:
Are they in tune with their body?
Do they focus on positives or negatives?
Do they talk about their emotional feelings or physical feelings?
Can they even answer the question?
Then they inevitably ask the same question of me, I answer, and we easily slide into a longer conversation.
At The Cleaning Station
This is one of my favorite and repeatable one-off jokes in the yoga studio…
There’s a little cleaning station where everyone lines up to clean off their mats.
If there’s a cute girl next to me in line, I’ll say:
“I don’t know why I even bother spraying down my mat, it’s always disgusting anyway.”
It gets a laugh at least 70% of the time. Because it’s a hot yoga studio, and we all have gross yoga mats.
At the Cubbies
If there’s a cute girl near me at the cubbies grabbing her stuff, I’ll apologize for being in the way, even if I’m not. It starts a conversation most of the time.
*Cutie, grabbing stuff from her cubbie near me*
Me: “Oh, sorry. I’m totally in the way.”
Her: “No, you’re good.”
Me: “Okay, cool. How do you feel after class?”
*Conversation continues*
Outside After Class
I almost never leave immediately after class.
I take my time, that way I can have a few moments of conversation with the teacher. Tell them exactly what I liked about class.
These series of 30-second conversations has led me to becoming friends with many teachers in my studio.
And I never put my shoes on in the studio. I wait to do it outside where other people are congregating after class, and there are sometimes people waiting for the next class.
If someone is sitting outside on the benches, waiting for the next class, I’ll sit next to them and say,
“Who teaches the next class?”
Granted, I’m a psycho and usually already know the schedule and who teaches, but it gives me a chance to chat with the person and learn about other teachers’ styles.
How I Start Conversations at The Park
I have a dog I bring to the park. If you go to a dog park without a dog to talk to strangers, it’s probably gonna come across as weird.
So everything I say in this section is “dog-dependent”.
Here’s my go-to conversation at the dog park (if I’m feeling brave enough to talk to people):
*I stand near an attractive woman.*
Me: “Which one is yours?”
Her: “Gingerbread, the terrier over there.”
Me [Compliments the dog somehow]: “I love her fur.”
Her: “Thanks! Which one is yours?”
Me: “The little poodle mix. Her name is Penguin.”
This might turn into talking about the dogs’ ages, playing styles, etc.
But I try to shift the conversation off the dogs as quickly as possible. Some people at the dog park talk about nothing but their dogs. They talk about their dogs like they’re people. It’s weird and I don’t like it.
I digress…
Pro tip: never interrupt a lady making out with her dog. You can’t save her, bro.
How I Start Conversations at the Gym
95% of the time, I don’t want to talk to anyone at the gym except:
My lifting partner
The dudes at the front desk
Other regulars
Even then, most conversations are short.
But sometimes, somebody catches your eye.
Warning:
Everyone says don’t hit on women at the gym. I agree with that.
But there’s a key:
“Hitting” on women.
I don’t hit on anybody. It’s a mindset thing. You “hit on” women by interacting with a goal in mind:
I want to get her number/have sex/get a date/etc.
It changes the entire vibe of the interaction.
Of course don’t start a conversation with someone in the middle of a set like a psycho.
But here’s the thing:
As time goes on, there are more and more places people say you can’t meet potential dates.
The gym
Work
Yoga
And on and on
The more places get added to the list, eventually, you take away all your opportunities for connection. And for what? So you can adhere to what some HR type on an Instagram reel said about “Creeps” in the workplace?
It’s nonsense.
If you see a cute girl who’s at the gym the same time as you, every day, I’d argue it’s rude NOT to say hello at some point.
I’m guilty of this. I could be better at introducing myself to all the other regulars.
But here’s how I’ve met one cutie at the gym:
There was a cute girl doing handstands in the HIIT area.
*Cutie hits a nice handstand*
Me: “Woah! Nice one!”
Her: “Thank you!”
Me: “I’ve been practicing mine a lot lately, but can’t seem to stick longer than 5 seconds.”
Her: “Let me see your form.”
I proceeded to try a few times, and she gave me some really good advice, which actually helped me stick it for 5 seconds. We were both so stoked, I just said we should go to a yoga sometime and we traded numbers.
How I Start Conversations at the Grocery Store
I think of this as the “Asking the Universe” conversation starter.
If I have something to say, or a question to ask, I’ll literally just say it out loud as though I’m saying it to the universe, and open the opportunity for whoever is near me will respond.
I’ll stand in the chocolate aisle at Whole Foods and say, “Now how the heck do you pick a chocolate?”
I’ll stand in front of all the green avocados and say, “These aren’t even close to ripe! What am I supposed to do with these?”
This works because it’s low pressure, it’s asking for help, and gives someone an opportunity to give advice.
“WTF even is a ramen noodle?”
I discovered it in college. There was this girl on the softball team I had the biggest crush on. I’d see her at the dining hall, the gym, on the quad—everywhere. But I was scared to talk to her. I told myself I had to wait until the perfect moment.
The perfect conversation starter.
Of course that led to me never saying anything at all.
Then one day I was loading up a plate at the dining hall. My female friend came up behind me. Still loading my plate, I said, “Why is the bacon always burnt here?”
To my shock, the voice that responded wasn’t my friend—it was the cutie I had a crush on. She answered like we were old friends and we had a nice conversation.
The lesson:
I didn’t need a perfect conversation starter. I just needed to say anything.
You’re Already a Community
Overall, the subtext of these conversation topics is:
“Hey, we’re a community here—how do we not know each other already?”
This is a very powerful mental model.
I’m dead serious when I say that having hundreds of these boring conversations has led to:
Making dozens of friends
Finding dates
Falling in love
Feeling at home in new places
I can’t overemphasize how much these boring conversation starters have changed my life.
I used to get anxious about what to say next. Even after saying hello, I'd stress about how to continue things and avoid awkwardness.
After practicing regularly, I realized you can't force conversations––they either flow or they don't. And if they don’t flow, you just say “See you around” and move on.
Conversations are a two-way street. If I'm at a loss for words, there's another equally complex person right there who can pick up the slack.