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Women Reveal 15 Of The Most Ridiculous Things Men Have Done On A First Date

By TSW Staff Updated September 8, 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: September 08, 2026
A couple on a first date.
©Mike Jones/pexels.com

First dates have a great impact as the first impression of someone can become their last. If they impress you, you would go for a second date and maybe a lifetime of togetherness might unfold after an impressive first date. But the same goes for failure to impress, many awkward interactions too can leave a permanent impression that lasts longer than you had initially thought and which makes you wonder if you ever want to experience that again with a new potential partner on a first date. Here are 15 such ridiculous stories that almost sound made up but are things women say they’ve experienced with men on a first date.

He Spent The Entire Date Talking About His Ex

A woman looks concerned while a man explains something with his hands open.
©Polina Zimmerman/Pexels.com

Starting off on the wrong foot is exactly how it feels when a man starts talking about his ex on his very first date with you. This may suggest he hasn’t fully moved on from his past relationship and could make it difficult for him to be fully present if things move forward between you. When his conversations keep revolving around a woman who already left you may end up wondering why were you even invited when the ex appears to be the real guest of honor.

He Brought Up Marriage Immediately

A man kneeling and proposing to a woman with a ring by a riverside city view.
@Olek Buzunov/Unsplash.com

It’s kind of strange when a man instantly starts pushing you for a serious commitment or marriage, like you have only just met and barely know each other. Some women reported some men took the discussion too far by talking about their future home, children and ideal wedding as well. If anything such intense discussions get extremely overwhelming if they are done on your first interaction.

He Couldn’t Stop Checking His Phone

A man using his phone during a date
©Curated Lifestyle/Unsplash.com

Some women encountered men who seemed impatient to meet but were constantly glued to their phone screen even while they talked. Repeatedly checking notifications, scrolling through social media, or answering calls instead of giving his date his attention reveals a lack of basic courtesy.

He Arrived Extremely Late Without A Good Explanation

A well-dressed, anxious man checks his watch while waiting at a restaurant table with flowers.
©Getty Images/Unsplash.com

Running late can have very legitimate reasons like getting stuck in traffic, encountering a last-minute task at the office or any other emergency, but if a man shows up late and doesn’t even apologize for ruining the evening. Women rarely find a man who doesn’t respect her time on the very first date ideal for a long-term partnership.

He Ordered For Her Without Asking

A man in a white shirt holds a food item toward a woman at a restaurant.
©Yunus Tuğ/Unsplash.com

Some men may think they are being considerate and thoughtful but this comes across as an attempt to undermine your autonomy and control your decision making. While making a recommendation is okay but simply deciding what another adult would have is downright ignorant of boundaries.

He Talked About How Much Money He Makes

A man with a beard and glasses sits at a desk, counting money with a laptop in front of him.
©Vitaly Gariev /Unsplash.com

While women quote they find self-confidence attractive in a man but a man who turns a first date into a financial presentation is just ridiculous. Some women have recounted experiences where a man mentioned his salary, assets, investments, or how much they paid for some expensive purchase. This makes them look cheap as a woman who wants emotional connection is not interested in knowing a man’s net worth.

He Was Rude To The Waitstaff

A waiter holds a tablet while a masked customer raises a hand toward him.
©Getty Images/Unsplash.com

A man reveals his true character by the way he treats strangers, like the salesperson, the waiter, or simply anyone who they don’t expect anything from. Women get turned off immediately when a man is dismissive, insulting, impatient, or unnecessarily rude to restaurant staff on the first date. Such conduct can suggest that this man gets unpleasant when things don’t go his way.

He Expected Her To Do All The Talking

A man sits silently opposite a woman on a balcony.
©Curated Lifestyle/Unsplash.com

First dates can be awkward for both parties but a man who dumps the entire burden of carrying the conversation on a woman while he stays quiet under the garb of shyness can leave a very offsetting first date experience for a woman. Women have had a negative view of such dating experiences where they had to break the silence while he contributed almost nothing. Conversations should be two-sided to ease the nervousness.

He Turned The Date Into A Job Interview

A woman looks uncomfortable as a man questions her at dinner.
©zahra karrami/Unsplash.com

On the opposite end is a man who made women feel like they had entered an interrogation. Asking their salary, their future goals, whether she wants children or not and would she accept a live-in arrangement with a partner? If a man asks you these later after some rapport has been established, then these can all be perfectly reasonable things to discuss but shooting these questions on the first date? Very disturbing.

He Spoke Almost Entirely About Himself

A man and woman sit in leather chairs holding cocktails while the man gestures broadly.
©Andrej Lišakov/Unsplash.com

Some first dates become all about himself. If anything this sends just one message: a man who is too self-absorbed and self-centered to focus on anyone beside himself. The entire date turned out to be about his career, hobbies, friends, workout routine, accomplishments, travels, opinions, and future plans. Being enthusiastic about your life is pretty cool, but completely ignoring the woman sitting across the table is definitely not impressive.

He Tried To Make Her Jealous

A woman jealous at who her man is texting.
©Getty Images/Unsplash.com


Casually flirting with other women, or mentioning how he’s wanted by so many women yet he chose to be with you or repeatedly talking about female friends can be his way to show how desirable he is. But pulling these cheap tactics on a first date can simply feel exhausting for a woman. You can’t be interested in a man who thinks he’s doing you a favor by being with you.

He Assumed She Would Pay For Everything

A woman paying bills from her debit card.
©Vitaly Gariev/Unsplash.com

Money talk on a first date isn’t ideal, but many women have reported first date experiences where the man carelessly ordered expensive food, and didn’t even pool or offer to pay the bill as if it were her responsibility. There’s no such rule as who pays but a gentleman would at least make an effort at generosity rather than showing outright entitlement by ordering freely and recklessly.

He Tried To Get Too Physical Too Quickly

A man in a suit and a woman in a dress talking intimately near a glass door, holding drinks.
©cottonbro studio/Pexels.com

Chemistry or instantly clicking with someone is fine but a man who tries to cross your physical boundaries on a first date is a major red flag. Many times men may feel they have a free pass to get physically intimate just because the first conversation got friendly and comfortable, like landing an unwanted kiss, excessively touching, or repeatedly ignoring your signs that you aren’t comfortable with physical touch shows he’s a red flag.

He Tried To Prove How “Alpha” He Was

A man receiving encouragement from a workout partner
©Getty Images/Unsplash.com

Some men seem to brag about fights, constantly talk about how they effortlessly get respect, or even go as far as turning completely ordinary situations into opportunities to establish dominance. Instead of leaving a strong impression, this trying too hard to appear macho may weaken their image. Someone who is genuinely confident usually doesn’t need to announce it every ten minutes on his first date with you.

He Behaved As Though She Owed Him Something

A distressed woman is talking to a man crying while sitting on a couch.
©Blake Cheek/Unsplash.com

Perhaps, out of all the 15 ridiculous behaviors the most uncomfortable first-date experience is when a man acts too entitled, as though paying for dinner, organizing the date, or showing interest automatically makes you owe him affection, attention, or a second date.

Final Thoughts

A couple on a restaurant date
©Curated Lifestyle/Unsplash.com

First dates, though rarely perfect, can have very powerful impacts either positive or negative ones. Both partners feel nervous, anxious, and have difficulty having a stress free conversation but still some behaviors like entitlement, control, or disrespect are dealbreakers and shouldn’t be excused as awkwardness. If something about a man’s behavior feels off, then trust your instincts and stay away from such a mismatch.

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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