Very few dates take your socks off — first metaphorically, then in the bedroom.
Most of them fall into the grey area — not bad but also not great. Then, there are the ones that suck because they don’t stop ranting about their ex or boring job. But that’s still better than awkward silence interrupted by desperate attempts to find commonalities. “Did you ever have a pet hamster?” is about as sexy as watching a colonoscopy on a hairy 70-year-old.
Small talk is tough. You can be the most interesting person in the world, but if you don’t break the ice, you’re stuck in silence city. You sit on hot coals, watching your spark slowly die like beached whale. You go home alone, take a sad shower, and think of all the witty things you could’ve said.
But there is a way around the boring and shallow conversations.
Asking the right questions makes you unforgettable, interesting, and creates a one-of-a-kind connection.
Instead of being strangers, you’ll feel like you’ve known each other for ages.
If You Want To Know Who Someone Is, Catch Them off Guard
There’s a question I’ve asked hundreds of times, not just on dates. Nobody has ever heard it before. Everyone’s baffled. And they all share something they usually wouldn’t.
If you were a fruit, which one would you be?
The answers are manifold.
A sweet and sour pineapple. A cherry that looks cute on the outside but has a tough core. A banana that’s full of energy but needs gentle treatment.
Asking about people’s fruity alter ego is memorable, shows you how they view themselves, and makes for a fun narrative further down the line.
So, which fruit would you be?
Remove the Fluff to Find Out What Really Matters
We only realize the true value of something once it’s gone.
Your life is no exception. Books like the Five Regrets of the Dying are filled with the last words of people who’ve realized their time on this planet isn’t limitless.
Instead of talking about the same fluff and superficial goals as always, you can find out what really matters to a person by asking:
When you die, what do you want people to say about you at your funeral?
I know what you’re thinking.
Death comes with negative emotions like sadness, anger, and grief. That’s fine. A good date isn’t all about feel-good topics and endless happiness. Without lows, there are no highs.
Both together create the emotional rollercoaster that makes for an unforgettable experience and deep connection.
Don’t Fall for This Common Trap
The most common lie is the word “good” following the question “How are you?”
It’s an automatic response wired into your brain from thousands of boring small talk interactions. I’ve met people on the verge of jumping head-first into a meat grinder telling me they’re “fine.” They just didn’t want to spoil the mood for others and burden them with their problems.
There’s always something that moves you, that you rack your brains about, that keeps popping back into your head when you’re trying to sleep at night. The person you’re dating feels the same, so ask them:
“Which three things do you think about most these days?
With this question, you’ll find out what moves them right now — their dreams and hopes, nightmares and fears.
If you want to connect with someone, these are the topics you need to explore.
How To Make Someone Tell a Story That Comes From the Heart
Your experiences have shaped you. From your parents’ treatment, over your high school friends, to traveling around the world. You’ve learned lessons that you’re eager to share — just like everybody else.
Get them to tell their story by asking:
If you could put up a billboard for everyone to see, what would you write on it?
I’ve dated a girl who would’ve used her billboard to educate other women about the risks of taking hormonal contraceptives. She had been hospitalized with thrombosis after being on the pill, a potentially deathly condition. Without this question, I wouldn’t have seen the fire in her eyes as she shared something she was deeply passionate about.
Ask people for their story — you’ll learn a thing or two in the process as well.
If You Want To Connect With Someone, Do the Opposite of Judging Them
Judging others is human. Your brain puts people into categories, an evolutionary mechanism helping you sort information. But quite often, your judgments aren’t accurate.
Instead of putting a hat on them that isn’t theirs, ask them:
What do people think about you that isn’t true at all?
Lots of people have said some version of “I didn’t think you’d be chill” to me. I always laugh because I get it. I’m a buff gym rat with tattoos, a cover model haircut, and a leather jacket. On the outside, I look like the tough alpha guy who came to lift weights, bang bitches, and be full of myself. On the inside, I’m a big softie with an open heart and a serious weakness for cute puppies — and nice booties.
I’ve also met a bunch of Onlyfans girls who most people would deem unapproachable and airheaded. Most of them were smart, warm, and interesting personalities.
Show your date that you aren’t one of the thousands of others putting hats on people.
Never judge a book by its cover.
The Rare Piece That Will Make Your Date Unforgettable
There is one simple ingredient that is key to all the questions you just read.
Without it, they’re useless — a drop in the endless ocean of boring conversations to nowhere.
With it, they’re money — a burning flame heating the forge of deep connections and fun encounters.
But before we get to it, let’s recap the questions you’ve learned so far:
- If you were a fruit, which one would you be?
- When you die, what do you want people to say about you at your funeral?
- Which three things do you think about most these days?
- If you could put up a billboard for everyone to see, what would you write on it?
- What do people think about you that isn’t true at all?
The key ingredient to all of them is rare in today’s world.
It’s genuine interest. Instead of ticking off a list, be curious about the other. Listen. Nod. Ask questions.
The most memorable date is one that shows you care.
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This post was previously published on MEDIUM.COM.
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