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Men Lay Out 15 of the Most Ridiculous Things They’ve Experienced With Women on a First Date

By TSW Staff Updated August 29, 2026

TSW Staff
TSW Staff Best Men's Watches Administrator
The Slender staff writers are watch enthusiasts and experts who love writing about watches and helping people find their next favorite timepiece.
Updated: August 29, 2026
A couple sitting at an outdoor café table, talking and smiling at each other.
©Nguyễn Thanh Tùng/Pexels.com

Listen, we need to talk about first dates and the absolute chaos some women bring to the table. Picture yourself sitting across from someone who seemed normal through text, excited to see where things go, and then she pulls out her phone to film a TikTok of her appetizer. Yeah. That happens. More often than you’d expect, actually.

The dating world has become a minefield of bizarre behavior that’ll have you mentally checking out before the check even arrives. Some of these things are so ridiculous (and weirdly common) that they deserve their own category of “what were they thinking?” moments. Buckle up.

She Live-Tweets the Entire Date Like You’re a Reality Show Character

A woman with short blonde hair holding a phone near a window, looking outside.
©Anastasia Shuraeva/Pexels.com

Watching someone pull out their phone every five minutes to update their followers about what’s happening right now is beyond weird. She’s literally narrating the date in real time, posting photos of the food, the drinks, maybe even sneaking a pic of you when you’re looking away. You’re sitting there realizing you’ve become content for her social media empire.

What makes this particularly annoying is how she filters every moment through “how will this look online?” instead of actually experiencing the date. You can practically see her crafting captions in her head while you’re mid-sentence. Why would anyone want to date someone who treats every interaction like it needs an audience? Hard pass.

She Won’t Stop Talking About Her Ex

A woman holding a glass of wine while talking with another person at a table.
©Gustavo Fring/Pexels.com

Bringing up an ex-boyfriend once in passing is fine, whatever, we all have history. But when she keeps circling back to stories about “this guy I used to date” every fifteen minutes? That’s a different story. You can tell when someone’s still mentally tangled up with their previous relationship, and honestly, nobody signed up to compete with a ghost.

The whole date becomes this weird therapy session where you’re supposed to nod along while she processes feelings she should’ve dealt with before downloading the dating app. Every story somehow leads back to what “Brad used to do” or how “things ended badly” and suddenly the entire evening feels like an audition for emotional support animal.

She’s Glued to Her Phone the Entire Time

A woman sitting at a table looking at her phone with a cup of coffee nearby.
©cottonbro studio/Pexels.com

There’s checking your phone once or twice for emergencies (totally reasonable), and then there’s what some women do, which is basically conduct their entire social media presence while you sit across from them trying to have a conversation. She keeps buzzing, scrolling, sneaky under-the-table texting… yeah, super attractive.

When you notice she’s more interested in her Instagram notifications than anything you’re saying, the interest dies right there. Why bother putting effort into conversation when she’s clearly got her attention divided between the date and whoever’s blowing up her DMs? She makes the message crystal clear: “This isn’t important enough for my full attention.”

She Expects You to Pay And Acts Entitled About It

A customer handing a card to a barista at a café counter while another person stands nearby.
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Look, plenty of guys are happy to pick up the check on a first date. That’s not the issue. She starts problems when she assumes you’ll pay, doesn’t even reach for her wallet (not even a token gesture), and then orders the most expensive items on the menu like she’s trying to max out someone else’s credit card.

You can spot the difference between appreciating someone’s generosity and treating a first date like an all-expenses-paid meal ticket. When she orders that third cocktail and adds an extra appetizer “for the table” while offering to split nothing… yeah, you notice. She kills any spark that might’ve been building with pure entitlement.

She Shows Up Looking Nothing Like Her Photos

A woman sitting on a bed in a softly lit room, looking down as she adjusts something.
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Everyone picks flattering photos. That’s normal. But when you show up to meet someone and have to do a double-take because the person standing there looks like a completely different human being? That’s a trust issue from minute one. Angles are one thing, but using photos from five years ago or filtering yourself into another dimension entirely is straight-up deceptive.

You feel misled from the jump. You showed up expecting to meet the person from the profile, and instead got someone who clearly put more effort into catfishing than being honest. Starting any potential relationship with that level of dishonesty… how’s that supposed to work out?

She Talks About Marriage and Kids on Date Number One

A woman smiling and resting her chin on her hand while talking to someone across a table.
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Nobody’s saying people shouldn’t have life goals or know what they want. But launching into detailed plans about wedding venues and baby names before the appetizers arrive? Relax. You can smell desperation from a mile away, and attraction dies faster than you can imagine when someone’s already planning the rest of your life together.

The whole thing feels transactional, like she’s interested in checking boxes on her life timeline rather than getting to know you as a person. “Will this guy marry me?” becomes the screening question instead of “Do we actually enjoy each other’s company?” She makes the pressure suffocating.

She Gets Visibly Drunk (And Sloppy)

A woman drinking wine from a glass while sitting at a dimly lit bar.
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Having a drink or two to ease first-date nerves? Totally fine. Downing five cocktails in an hour and becoming a slurring mess who can barely sit upright? That’s a disaster. You find yourself babysitting instead of dating, and that’s what nobody signed up for.

Beyond being unattractive, this raises serious questions about judgment and self-control. Watching someone completely lose the plot on a first date makes you wonder what other situations might spiral out of control. Plus, you’re now stuck figuring out how to safely get her home instead of enjoying the evening.

She Only Talks About Herself the Whole Night

A woman resting her chin on her hand while talking to a man at a café table.
©Roman Biernacki/Pexels.com

Some women turn first dates into autobiographical monologues. Every question gets redirected back to her life, her job, her opinions, her weekend plans, and meanwhile, you’re sitting there wondering if she even remembers your name. You need back-and-forth to have a conversation, but this feels like a one-woman show.

After an hour of barely getting a word in, you check out mentally. What’s the point? She’s made it crystal clear the only perspective that matters is hers. Dating someone that self-absorbed sounds exhausting, and you can picture exactly how every future interaction would go (exactly like this one).

She Criticizes Everything You Say or Do

A man in a suit holding a drink at a bar while looking off to the side.
©cottonbro studio/Pexels.com

She stays in constant correction mode, which is such a turn-off. You mention you like a certain movie. “Ugh, really? That’s so basic.” You order a particular drink. “I can’t believe people still drink those.” You share an opinion. “Well, actually…” The whole date becomes an exercise in being made to feel inferior.

You pick up on condescension immediately. When someone spends the entire evening making little digs or acting intellectually superior, you lose all attraction. Dating should feel good, not like defending yourself in court. Why would anyone want to pursue something with someone who makes them feel inadequate from the jump?

She Brings Her Friend Along (Without Warning)

A group of people sitting at a table with drinks, talking and socializing indoors.
©cottonbro studio/Pexels.com

Imagine showing up for what was supposed to be a one-on-one date and discovering her best friend tagged along “for moral support.” Now the whole dynamic turns into this awkward third-wheel situation where you’re trying to make conversation while two people have inside jokes and whispered conversations right in front of you.

This signals massive trust issues or immaturity. Either she couldn’t handle meeting a stranger alone (concerning) or she thought ambushing you with an audience was acceptable (also concerning). Either way, she ruins the date before it starts. Nobody wants to perform for an audience when they’re trying to make a genuine impression.

She Makes Every Topic Political or Preachy

A man and woman sitting by a window, drinking coffee and talking.
©Mike Jones/Pexels.com

Having strong opinions are fine. Turning every single conversation into a lecture about politics, social issues, or whatever cause she’s currently championing? Exhausting. First dates should have some lightness to them, but some women treat them like opportunities to convert people to their worldview.

After the fifth rant about something tangentially related to what you said, you mentally tap out. There’s a time and place for deep discussions about serious topics, but weaponizing every casual comment into a platform for preaching makes the whole thing feel hostile. Dates should be enjoyable, not like attending someone’s TED Talk.

She Keeps Comparing You to Other Guys She’s Dated

A man drinking coffee while sitting across from a woman in a dimly lit setting.
©Pavel Danilyuk/Pexels.com

“My last boyfriend always took me to nicer places than this.” “The guy before you was way taller.” “I usually date men who make more money.” Cool story. Why is she even here? When a woman spends the date making unfavorable comparisons, you’re wondering why she agreed to meet up in the first place.

These comments don’t motivate anyone to try harder. They signal she’s settling or keeping you on a ranking system you never asked to be part of. You want to feel like someone’s excited to be there with you, specifically, not like you’re being measured against an invisible lineup of exes.

She Acts Completely Different Than Her Texting Personality

A woman standing by a window, looking at her phone with her reflection visible in the glass.
©Andrew Patrick Photo/Pexels.com

Her messaging suggested someone fun, interesting, engaged, and then she shows up and gives one-word answers while staring at the wall. You feel the disconnect immediately. You start wondering if you were texting a completely different person or if she lost all interest the second things became real.

Catfishing works both ways. When someone’s personality through text was engaging and enthusiastic but in person she’s withdrawn or cold, you feel bait-and-switched. You put effort into building that pre-date rapport and suddenly feel like you wasted all that time because the person who showed up bears no resemblance to the one you were messaging.

She Asks Invasive Questions Way Too Early

A man and woman sitting on a balcony, drinking wine and relaxing together.
©cottonbro studio/Pexels.com

“How much money do you make?” “Why did your last relationship end?” “Do you own or rent?” Some women treat first dates like job interviews, firing off intensely personal questions that make the whole thing feel transactional. There’s getting to know someone, and then there’s conducting an interrogation.

You shut down when she crosses into territory that feels invasive for a first meeting. Building interest requires some mystery and gradual revelation, not laying everything out like a resume review. She makes you feel like you’re being screened for qualifications rather than someone wanting to connect as humans with all that aggressive questioning.

She Name-Drops Every Expensive Thing She Owns or Places She’s Been

A woman and a man sitting indoors, each drinking a glass of wine.
©Pavel Danilyuk/Pexels.com

Some women spend the entire date casually mentioning their designer purse, their recent trip to the Maldives, their luxury apartment downtown, or how they “only drink this specific brand of champagne.” She never stops flexing. Every topic somehow circles back to how much money she spends or how upscale her lifestyle is.

She screams insecurity wrapped in labels with all that constant bragging, and honestly, it’s exhausting to listen to. You start wondering if she’s actually interested in you or if she’s auditioning you to fund her lifestyle. Either way, the whole thing feels shallow and transactional. Nobody wants to date someone whose personality is a walking luxury catalog.

Categories: Best Men's Watches

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TSW Staff

About TSW Staff

The Slender staff writers are watch enthusiasts and experts who love writing about watches and helping people find their next favorite timepiece.

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