Ever wondered what it’s like to go on a date with one of those dating coaches we see constantly popping up on our socials?
Instagram and TikTok are flooded with reels telling us what red flags to watch for, how to set better boundaries and why we should run for the hills if a man so much as blinks the wrong way on a first date.
And I’ll admit it. I shamelessly devour them all.
When a man by the name of Benny Hart started popping up on my Instagram feed under the name Bennyinc, confidently dishing out dating advice from a very New York, very no-nonsense male perspective, I leaned in. Hard.
As did more than half a million other women, judging by his follower count.
Because let’s be honest. It’s one thing to hear another woman say, ‘Run if he makes you split the bill.’ But it lands a little differently when it’s coming from a straight-talking, alpha-presenting New Yorker, who looks like he’s just wandered out of a job in finance and into your DMs to tell you the truth.
So, when I found myself in New York this week, I did what any confident, modern woman would do.
I slid into his DMs and asked if he wanted to meet up.
When a man by the name of Benny Hart started popping up on my Instagram feed, confidently dishing out dating advice I slid into his DMs and asked if he wanted to meet up
It’s one thing to hear another woman say, ‘Run if he makes you split the bill.’ But it lands a little differently when it’s coming from a straight-talking, alpha-presenting New Yorker
Because newsflash, girlies: it is perfectly acceptable to make the first move. Benny himself has preached this in multiple reels. So really, I was just following professional advice.
Thankfully, he said yes.
Benny has built a huge following breaking down modern dating dynamics, has appeared on multiple relationship podcasts and has even written a book on mindset and attraction.
He’s also famous for his blunt advice, including gems like: if you can’t envision anything after date two, stop. And my personal favorite: don’t you dare waste someone’s time, money or energy if you’re not that into them.
Ironically relevant. But we’ll get to that.
Now what started as a casual invite by me for drinks was followed up with some short, blunt answers from him. This was not what I was expecting from a dating coach. I’ll admit I was hoping to be razzle dazzled with some witty repartee. I wanted to be wooed. Instead, my advances were met with rather underwhelming responses like, ‘Yeah, I’d be down.’ And, ‘Sure.’
Hmm… perhaps that should have been my first clue for how the end of the night would play out. But going against my gut feelings, has been a fairly consistent dating technique of mine. And I annoyingly stuck to it.
Instead, I romanticized the whole thing in my mind. Convinced that we would bond over our mutual interest in the world of dating and psychology.
In preparation for our drinks at Hotel Chelsea, I raced to Chinatown for one of the famous blow outs all the TikTok influencers are raving about, and for 30 minutes of bliss I got the most amazing massage and hair wash-and-dry of my life.
It’s amazing what a good blow out can do for one’s self-confidence, especially before a date – I highly recommend it.
But then I made the rookie error of going to a pre-arranged drinks with friends first on an empty stomach, and we all know that’s not a good idea.
So, I’ll admit, I turned up to the date a little late and a little buzzed.
Meanwhile, Benny arrived early at the Hotel Chelsea, waited patiently and greeted me with a big smile and a hug. He was slightly shorter than I expected, but somehow more handsome.
He apologized for smelling like cigar, which I found strangely arousing and honestly, only added to his already alpha vibes.
I’ll admit, I turned up to the date a little late and a little buzzed.
Benny Hart (pictured) arrived early at the Hotel Chelsea, waited patiently and greeted me with a big smile and a hug
He immediately put his card down at the bar and ordered drinks, which made me quietly note that yes, he does practice what he preaches. This was looking promising.
Now, I’ve encountered plenty of influencers in the wild. At brand parties, awards nights and whatever hotspot is trending that week. And I’m often disappointed to discover they’re either wildly underwhelming, or deeply dull and apparently saving every ounce of charisma for when the little red recording light comes on.
Not Benny. What I quickly realized makes Benny different from the sea of shirtless TikTok dating gurus is that he didn’t just wake up one morning and decide to start yelling about attachment styles online.
Before becoming a social media dating coach, he was very much an office-job, tech and business guy. He studied psychology and biology, co-founded a digital fitness platform in his twenties, worked as a CEO and mindset coach, and even spoke at universities and major institutions about human behavior and communication.
We love a man with an impressive resume.
Somewhere along the way, women started asking him less about leadership and productivity and more about why dating felt so broken. Turns out the same mindset principles that work in business apply just as neatly to relationships.
The result is a dating coach who doesn’t talk in fluffy affirmations, but in clear, sometimes uncomfortable truths. Which, as half a million women seem to agree, is exactly what we’ve been missing.
And here he was, this confident, straight, New York man who isn’t afraid to tell you when you’re the problem, sitting right in front of me sipping on a tequila on the rocks.
And dear reader, this is where I went wrong a second time.
What I should have done, according to literally every dating expert ever – including Benny himself – was end the date early and leave with a bit of mystery.
Instead, I had two martinis and a glass of extra confidence.
I casually suggested we head across town to the restaurant Balthazar, because I had arranged a quick meet-and-greet with owner Keith McNally, whose memoir I had recently devoured. So off we went.
And this is where the night turned into a comedy of errors, the errors being mine, and the joke being very firmly on me.
What I should have done, according to literally every dating expert ever – including Benny himself – was end the date early and leave with a bit of mystery
I had two martinis and a glass of extra confidence
Error number three: I got extra tipsy.
Error number four: I completely abandoned Benny at the bar while I enthusiastically bonded with Keith who, by the way, was every bit as witty and unfiltered as I’d hoped. Just as glorious as he is in his book and in the press, like the time he publicly called out James Corden for being rude to his staff.
I was in heaven. Poor Benny, alone at the bar, was not.
I eventually returned to him, and a glass of champagne which I wish I could blame for my next mistake. Giddy with the night – and let’s be honest, the martinis and bubbles – I chirpily told Benny, ‘I’m so glad we went on this date.’
He gently but firmly corrected me. It was not a date, just a catch-up. To be fair to straight-talking Benny he certainly follows his own dating rules: no timewasters here, no leading a girl on. If I were a balloon, that would have been the exact moment I deflated.
How mortifying.
Turns out I should have listened more closely to Benny’s advice about clarity and expectations. Or maybe defined what ‘a drink’ meant before booking a blow-out and buying a new outfit.
So, what’s it like to date a dating coach? Honestly, I still don’t know.
But I do know that dating in 2026 remains deeply humbling, mildly humiliating, and far tougher than any Instagram reel makes it look.
Stay strong girlies, it’s a jungle out there.
