Every guy has been there. You’re on a date with a woman you actually like, you’re trying to impress her, and somewhere along the way… something goes wrong. The chemistry fizzles, the conversation is replaced by awkward silences, and by the end of the night, you’re left wondering what exactly you did wrong.
The truth? Most men don’t fail to impress women because they’re not good-looking enough, wealthy enough, or charismatic enough. They fail because they’re unknowingly making mistakes that instantly kill the vibe.
Some of these mistakes come from bad dating advice. Others? Just pure social oblivion. But if you want to avoid becoming another guy she ghosts, it’s time to rethink your approach.
Here are some of the biggest mistakes men make when trying to impress women—and what you should be doing instead.
Story Stages
1. Acting Disinterested to Seem ‘Cool’
Somewhere along the line, men got the idea that playing it cool meant acting like they didn’t care. You know – that whole “treat ‘em mean, keep ‘em keen” mindset. They think that by holding back affection, keeping conversations vague, or pretending not to be too interested, they’ll make a woman work harder for their attention.
Surprise, surprise – it never works.
Most women aren’t looking for a man who plays mind games. They want genuine engagement, a little excitement, and someone who shows interest. If she feels like she’s pulling teeth just to get you to talk about yourself or show enthusiasm, she’s going to assume you’re either boring or just not that into her—and she’ll lose interest just as fast.
Emily, 29, put it bluntly:
“If I have to guess whether or not a guy actually likes me, I’m not sticking around to find out. If you’re interested, show it. If you like her, act like it. Not smiling, not making eye contact, and not asking questions just shows you’re wasting my time.”
2. Flirting With Other Women to Make Her Jealous
There’s a particular brand of bad dating advice that tells men that women love competition—that if they see other women interested in them, they’ll want them more. So what do some men do? They flirt with other women right in her presence, hoping to spark jealousy.
This is a bad, bad idea… used by the kind of guys that have watched one too many movies.
Rather than making a woman want you more, it just makes you look like an arrogant, insecure asshole. She won’t see you as the desirable, high-status man you’re hoping to mimic—she’ll see you as someone who needs validation from multiple women just to feel important.
We reached out to Top Models Agency and spoke to Maggie, one of their popular high-class London escorts, who has been on dates with some of the world’s wealthiest men. Here’s what she had to say about men who pull this move:
“I’ve had clients try to act like they have women lining up for them, thinking it’ll make me want them more. It does the opposite. If you’re secure, you don’t need to prove your worth by flaunting other options. Women pick up on that immediately. If you want to impress a woman, make her feel like she’s the only one in the room. Do that, and you’re already in her good books.”
3. Overcompensating With Flashy Gestures
There’s nothing wrong with wanting to impress a woman with a nice dinner, a well-planned date, or a thoughtful gift. The problem is when men go overboard—dropping serious money on a first date or bragging about their wealth.
Most women don’t care how expensive the restaurant is if you can’t hold a conversation. And a designer watch won’t make up for an awkward personality. Money and status might grab her attention for a minute, but they won’t hold it if there’s nothing else behind it.
Jessica, 31, put it best:
“If a guy picks me up in a luxury car but spends the whole date name-dropping, flexing his job, and showing off, I tune out. Don’t get me wrong – a confident man is sexy, but insecurity wrapped in a Rolex isn’t.”
4. Being Too Needy or Clingy
On the opposite end of the spectrum, some men try too hard to win a woman over. They text too much, they try to see her every day, and they shower her with compliments before they’ve even really gotten to know her.
It comes from a good place—after all, who doesn’t like feeling wanted? But too much too soon can feel suffocating.
If anything, it makes you seem low value. A woman wants to feel like she’s earned your affection, not that you’re ready to wife her up after one date. If you start acting like you need her validation, constantly seeking reassurance, or getting upset when she doesn’t text back immediately, you’re going to lose her fast.
Hannah, 27, explained it like this:
“I remember meeting someone for a first date and actually getting on well with him. But then, within just 10 minutes of meeting, he was already planning our future kids’ names, and asking which were my favourite. Yeah, after that, I was doing all I could to get the date over and done with fast.”
5. Thinking Confidence Means Acting Like a D**k
There’s this big rumour going around that women only like bad boys—that the key to attraction is being dominant, dismissive, or even slightly mean. And while confidence is attractive, there’s a fine line between being assertive and just being a dick.
Women don’t fall for bad boys because they’re jerks—they fall for them because they’re decisive, self-assured, and not afraid to go after what they want. The problem is when guys mistake arrogance for confidence and end up coming off as insufferable.
Sarah, 33, made this painfully clear:
“I love a guy who knows what he wants. A guy who thinks being rude is the same thing as having confidence? Not so much. If I feel like I’m on a date with an Andrew Tate fan, I’m walking out.”
So, What Actually Works?
If you take anything away from this, let it be this: Trying too hard (or not trying at all) will kill attraction fast.
Instead of trying to impress a woman, focus on building a connection with her. Be genuine, confident, engaged, and self-assured—without resorting to games, mind tricks, or overcompensation. See? It’s pretty simple, really.
