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16 Things Women Pretend to Like on First Dates (But Actually Hate Them)

Updated on November 3, 2025 by TMM Staff · Dating & Confidence

A man in a suit with a drink in hand has his arm around a woman in a light-colored dress.
©cottonbro studio/Pexels.com

First dates are funny because half the time, everyone’s faking something. The smiles, the nods, the “oh wow, that’s so interesting” replies. Women, especially, have mastered the art of pretending to be charmed while secretly wondering how fast they can leave without looking rude.

Sometimes, women pretend to like something a guy says just because they want to give a guy a fair shot. Maybe he’s nervous, maybe it’s the lighting, maybe he’s not usually this much. But by the time the appetizer hits the table, they already know if this is going anywhere.

Here’s the truth you won’t find in any dating guide. The stuff she’s enduring while saying, “No, really, it’s fine.”

Table of Contents

Toggle
  • 1. Long Stories About Gym Routines
  • 2. “Funny” Stories That End With “You Had to Be There”
  • 3. Fancy Restaurants Where You Can’t Pronounce Anything
  • 4. Over-Explaining “Man Stuff”
  • 5. Overly Aggressive Flirting
  • 6. Endless Talk About Exes
  • 7. Trying Too Hard to Impress the Waitstaff
  • 8. Overdoing the “Gentleman” Act
  • 9. Talking About Money or “Success”
  • 10. Ordering for Her
  • 11. Talking About How “Chill” You Are
  • 12. Making Everything a Debate
  • 13. Excessive Phone Checking
  • 14. Fake Deep Conversations
  • 15. Over-Complimenting Her Looks
  • 16. Acting Like a Walking Dating App Profile

1. Long Stories About Gym Routines

A man working out on a chest press machine in a gym.
©Alesia Kozik/Pexels.com

We get it. You love to work out. She’s nodding, pretending to care, but her soul left the table three flex stories ago.

Talk about the gym once, but make it your personality? No. Unless your date’s wearing a “Born to Squat” hoodie, save it for your workout buddies.

2. “Funny” Stories That End With “You Had to Be There”

A man and woman laughing together while sitting close indoors.
©cottonbro studio/Pexels.com

If she has to fake-laugh, she’s dying a little inside. When a guy starts a story with “You’ll love this,” and it ends with “Guess you had to be there,” she’s silently praying for the check.

And you know what’s worse? When he laughs so hard at his own story, he snorts. She’ll giggle to be polite, but her inner voice is already packing its purse. If you’re telling a story, make it about something she can join in on.

3. Fancy Restaurants Where You Can’t Pronounce Anything

A person reading a restaurant menu at a table.
©cottonbro studio/Pexels.com

At first, she’ll act impressed. But after ten minutes of pretending she knows what “foie gras espuma” means, she’s over it.

A good date doesn’t need imported truffle dust. It needs good food, real laughs, and a place where she doesn’t have to whisper her order like she’s summoning a demon. She’d rather split tacos and laugh too loud than sit somewhere so fancy she’s scared to sneeze.

4. Over-Explaining “Man Stuff”

A man and woman sitting at a small table with two glasses of wine.
©cottonbro studio/Pexels.com

You know that tone? The one where a guy explains whiskey, poker, or car engines like he’s tutoring a child? She hates that.

She’s not nodding because she’s impressed. She’s nodding to avoid saying, “You think I’ve never heard of horsepower before?” The real flex is talking to her about stuff that she finds interesting.

5. Overly Aggressive Flirting

A man kissing a woman’s hand while she smiles outdoors.
©Gustavo Fring/Pexels.com

A little charm goes a long way, but leaning across the table like you’re in a music video? She’s not swooning. She’s planning her exit route.

Compliment her once and let it breathe. No one enjoys dodging a verbal tongue twister of pickup lines. And if you’re staring too long, congratulations, you’ve crossed from flirty to “this is getting weird” territory.

6. Endless Talk About Exes

A woman smiling at a man while sitting at a table with two empty glasses.
©iam luisao/Pexels.com

Everyone’s got history, but the first date isn’t the place for a breakup documentary. She might nod politely, but inside she’s thinking, Why am I hearing about your emotional damage over appetizers?

Bringing up your ex every few sentences is like inviting a ghost to dinner. If she wanted a haunting, she’d watch Netflix.

7. Trying Too Hard to Impress the Waitstaff

A person pouring red wine into a glass at a table with others.
©Pavel Danilyuk/Pexels.com

There’s confident, and then there’s treating the waiter like your stage audience. Watching someone turn the poor server into part of their show is cringe in real time.

She doesn’t care if the waiter “knows you.” She cares if you’re kind. Being polite beats being a showboat every single time. And if you’re tipping like you’re tossing coins in a fountain, she’ll notice that too, and not in a good way.

8. Overdoing the “Gentleman” Act

A woman in a black dress and a man in a tuxedo sitting closely together on a couch.
©cottonbro studio/Pexels.com

Opening the door? Great. Yanking it open so fast she almost trips? Weird. Chivalry’s cute until it starts feeling like a play rehearsal.

Pull her chair out, sure. But let the gesture feel natural, not like you practiced it in the mirror a thousand times.

9. Talking About Money or “Success”

A man in a suit standing at a bar with drinks in front of him.
©MART PRODUCTION/Pexels.com

Dropping hints about your income or car brand is the last thing a woman wants to hear on a first date. She’s pretending to be impressed, but really, she’s tallying red flags.

If you’re bragging about your “multiple revenue streams,” she’s wondering how soon she can stream away from you. Ask her about what she loves, not how much you spent on your “Omega Speedmaster”.

10. Ordering for Her

A woman smiling while holding a slice of avocado toast and looking at someone.
©cottonbro studio/Pexels.com

Old-school charm? No. Please no. Even if she smiles and says “That’s fine,” she’s probably fuming inside.

She can speak for herself. Unless she literally said, “Please order for me,” don’t do it.Bonus cringe if you say, “Trust me, you’ll love this.” Well, she won’t.

11. Talking About How “Chill” You Are

A close-up of two people sitting and holding takeaway coffee cups.
©John Diez/Pexels.com

Anyone who keeps saying they’re chill isn’t. When a guy repeats, “I’m super easygoing,” she’s already bracing for the meltdown later.

If you’re actually a chill dude, she’ll feel it. If you have to sell it, you’re probably not. The biggest irony? The “chill” guys are always the ones who panic when the date doesn’t go their way.

12. Making Everything a Debate

A man and woman sitting by a campfire and talking outdoors.
©Pavel Danilyuk/Pexels.com

Some men treat dates like podcasts, interrupting, challenging, and turning casual chat into “point-counterpoint.” She’ll smile through it, but inside she’s screaming, This isn’t a panel discussion, dude.

You don’t need to agree on everything, but turning her every sentence into a sparring match is the fastest way to guarantee there won’t be a second date. Debate your friends. Flirt with your date.

13. Excessive Phone Checking

A man sitting at a restaurant table using his phone with wine glasses nearby.
©Jep Gambardella/Pexels.com

There’s no faster way to kill chemistry than constant screen-glancing. She might pretend it’s fine, but she noticed every single time.

Put the phone down. Look her in the eye. The text can wait. And if it can’t, she won’t either. Nothing screams “you’re not important” louder than someone scrolling mid-sentence. You’re not that busy: You’re on a date, not running NASA.

14. Fake Deep Conversations

A man and woman sitting at a table having a serious conversation over a meal.
©Tima Miroshnichenko/Pexels.com

Asking, “So… what’s your purpose in life?” before dessert is just… awkward. She’s pretending to reflect, but really she’s thinking, “Sir, I met you an hour ago.”

Talk about your worst vacation, your weirdest job, the time you ruined Thanksgiving. That’s where the real bond forms. Keep the “meaning of life” talk for when she actually likes you.

15. Over-Complimenting Her Looks

A man and woman sitting in a café having a conversation over coffee.
©Pavel Danilyuk/Pexels.com

Compliments are great, until they start feeling like a script. “You’re gorgeous. Stunning. Unreal. Flawless.” It goes from flattering to weird fast.

One sincere compliment beats a dozen rehearsed ones. Tell her what stood out. Her laugh, her sarcasm, the way she talks about something she loves. That’s how you make her feel seen. Otherwise, you’re just another guy reading from the same tired playbook.

16. Acting Like a Walking Dating App Profile

©William Fortunato/Pexels.com

Some guys treat first dates like they’re reading their own bio out loud. “I’m really into hiking, I love dogs, I’m super spontaneous.”

Look, she wants the real thing. Talk like an actual person. Tell her about the worst camping trip you’ve ever had, or the time your dog stole a whole rotisserie chicken. Give her a story that feels alive, not a resume that sounds recycled.

Dating & Confidence

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About TMM Staff

The Modest Man staff writers are experts in men's lifestyle who love teaching guys how to live their best lives.

If an article is published under TMM Staff, that means multiple writers worked on it. For example, sometimes several of us have experience with a certain brand, so we collaborate to publish a more thorough review.

Or, if an article was originally written by one person, but then it was updated by someone else, we'll re-publish it under TMM Staff.

Remember: all of our articles (including those below) are written by real people with decades of combined experience in men's fashion and lifestyle topics.

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