You can usually spot it from across the room: the rehearsed line, the story that’s really a brag, the joke that arrives whatever was just said. Trying too hard comes from wanting it to go well, which is understandable. But people warm to someone who’s relaxed and paying attention, not someone performing.
What trying too hard looks like
Canned openers, showing off, compliments about looks to someone you’ve just met, forced jokes, name-dropping and talking fast to fill every gap. The common thread is that it’s all about how you come across, not about the person in front of you.
Drop the canned lines
Lines you found online sound like lines you found online. A plain comment about the moment beats any clever opener: the line, the music, the photo on their profile. How to Start a Conversation With a Stranger has plenty that work.
React to what they actually said
Listen to the answer and respond to it, instead of waiting to deliver your next prepared bit. A real reaction to something surprising they’ve said is more charming than any material you could bring.
Let them find out the good stuff
You don’t need to fit your job, your travels and your half marathon into the first five minutes. Impressive things land better when they come up naturally, or when someone asks. How to Talk About Yourself Without Bragging helps.
Be funny about the situation
Humor that comes from the moment works. Jokes you’ve told before, at someone’s expense or to prove how quick you are, tend to fall flat. How to Be Funny in Conversation covers the difference.
Skip the looks compliments early on
Telling a stranger they’re gorgeous puts them on the spot. A compliment about a choice they made, like a book, a song or a well-named dog, is easier to receive and starts a real conversation.
Slow down
Talking fast, filling every pause and laughing at your own jokes all read as nerves. Breathe, let a silence sit for a second and let the other person carry some of the conversation too.
Be fine with being ordinary
Most good conversations are made of ordinary things: food, weekends, terrible bus routes. You don’t have to be impressive to be good company. Being easy to talk to is the impressive part.
Show a little of the real you
Admit you’re terrible at bowling, that you’re a bit nervous or that you’ve never seen the movie everyone loves. Small honest admissions help people relax, because you’re clearly not putting on a show.
Let it go if it doesn’t click
Trying harder when someone isn’t interested only makes it worse. A friendly exit is a good result, and it leaves a better impression than any clever line. How to End a Conversation Gracefully shows how.
Lines to borrow
- Instead of a pickup line: “Okay, I have to ask about the dog in sunglasses.”
- Reacting for real: “Wait, go back. You won a pie-eating contest?”
- Instead of a looks compliment: “Good choice on the book. Is it as good as everyone says?”
- Admitting something: “Full disclosure: I’ve never seen it. Please don’t leave.”
- A relaxed exit: “I’ll let you get back to your friends. Really glad I said hello.”
Practice it
The Hey starts with a one-word message on a dating app, where a canned line is the easiest mistake to make. Rooftop Bar puts you in front of a group of friends who will notice any act straight away.