Blind Date Horror Story: The Entitled Woman Who Treated Him Like a Free Wallet

Some people say modern blind dates are no longer about seeing if two people click—they’re basically a full-scale test of human character.

Today I’m sharing my coworker’s wild, cringey, infuriating real blind date story that’s full of red flags from start to finish.

After reading this, you’ll definitely realize some people take taking advantage of others and acting entitled to a whole new level.

1. Instant Great First Impression; The Guy Was Sincere From the Start

Last month, my coworker went on a blind date set up by a mutual acquaintance.

He’s a down-to-earth guy with solid morals, and he took the blind date super seriously without any half-hearted attitude.

For their first meetup, he bought her flowers ahead of time and picked a hot pot restaurant for dinner.

The conversation flowed really smoothly the whole time—they laughed and chatted nonstop with zero awkward silences.

After the date wrapped up, she texted him back right away with a warm, easygoing tone.

He was totally smitten on the walk home, humming songs the whole way, over the moon with how well it went.

When his mom asked how the date went once he got home, he wouldn’t stop gushing about her: She’s outgoing, open-minded, and so easy to hang out with—this could really go somewhere.

His mom got instantly excited and pushed him hard to make a move: Ask her out again fast! Don’t let such a nice girl slip away!

2. She Agreed to the Second Date Instantly; He Thought He Had It Locked

Following his mom’s advice, he texted her that same night: Are you free this weekend? Wanna hang out somewhere?

She replied within a second: Yeah! Where should we go?

Seeing how eager she was, he fully relaxed, convinced the blind date was a guaranteed success.

No one could’ve guessed every good impression only lasted through the first date. The second outing completely changed his perspective on everything.

3. The Second Date Takes a Sharp Turn; She Brought a Plus-One to Mooch Off Him

That weekend, she suggested checking out a brand-new trendy shopping mall downtown.

He agreed without hesitation. He offered to drive and pick her up, but she turned him down flat: No need to drive me, let’s just meet at the mall entrance.

He didn’t think anything of it, showed up early to wait, and even grabbed her a bubble tea as a nice gesture.

Everything was fine while they browsed stores at first—until they hit a women’s clothing shop, and the whole vibe shifted.

She spotted a trench coat priced over $110, tried it on repeatedly, kept checking herself in the mirror, and kept glancing over at him the whole time.

He’s a straightforward, oblivious nice guy, and it never crossed his mind to offer to pay for it unprompted.

When she realized he wasn’t picking up the tab, she quietly hung the coat back up and said flatly: Let’s keep looking then.

The awkward tension in that moment was obvious to anyone watching.

By noon, she said she was hungry, so they headed upstairs for grilled fish for lunch.

They were supposed to have a quiet one-on-one meal, but halfway through eating, she suddenly said: My best friend’s nearby—would it be okay if she joins us?

Bringing a random third person to an exclusive second date is such a boundary violation.

He felt uncomfortable deep down, but didn’t want to be rude, so he nodded and said it was fine.

4. Her Best Friend Shows Up and Orders Nonstop Free Food Without Asking

Ten minutes later, her friend rushed over to the table.

Here’s the worst part: the friend had zero manners whatsoever. She grabbed the menu immediately, added three expensive entrees and two fancy cocktails without even asking the guy’s opinion.

The final restaurant bill hit roughly $55.

The most cringey moment of the whole day came when it was time to pay:

Both girls stared down at their phones the entire time, pretending they couldn’t see the check sitting on the table. They silently coordinated to avoid offering to split the bill or chip in at all.

He sat there awkwardly for a full minute, watching neither girl make the slightest move to pitch in, so he had no choice but to foot the entire bill alone.

He thought lunch would wrap up the day’s plans, but then her friend egged them on to head down to the arcade downstairs.

The two girls grabbed his arm and dragged him along, treating him like a built-in ATM the whole time.

They spent the whole afternoon playing claw machines, messing around, and having a blast at his expense.

Her friend even joked out loud in front of everyone: Tell your boyfriend to buy more game tokens!

The girl he was dating didn’t deny it or correct her—she let everyone assume they were a couple and that he was obligated to cover everything.

At that exact moment, my coworker’s heart sank completely.

5. He Spent Over $90 Total, Then Got Abandoned At the Mall Entrance

By four in the afternoon, he’d lost all desire to keep hanging out, so he said he wanted to call the date off early.

She only mumbled a dismissive “okay” and immediately walked off to keep shopping with her friend.

Not a single word of thanks, no goodbye, zero guilt. She left him alone at the mall entrance after he’d dropped over ninety dollars and entertained them all day long.

He walked back to his car by himself, seething with frustration. He’d given her genuine care and got taken advantage of; he’d poured his energy into her and got treated like his effort was nothing more than an obligation.

6. He Broke Things Off, and She Turned Around to Play the Victim

Once he got home, he vented the whole miserable experience to his mom—over ninety dollars wasted and endless disrespect all day.

At first his mom tried to rationalize it: Girls just test how generous you are on dates, that’s all.

He saw right through the act immediately: This isn’t a test—she’s just using me as a sucker to pay for everything!

He thought that was the end of the whole mess, but the plot twisted again that night.

The girl texted him out of the blue: I had so much fun today! We should go to a hot spring resort next time!

Reading that message snapped him fully out of his crush, and he replied calmly: I don’t think we’re a good match for each other.

That one single line made her flip her entire attitude instantly, firing off three question marks back-to-back: Are you mad about spending money???

Her warped logic was unbelievable: Mooched meals and entertainment are her birthright, his money and effort are non-negotiable, and if he draws a line he’s just cheap.

He didn’t bother arguing and stopped replying entirely.

Less than ten minutes later, the matchmaker who set them up called his mom to tattle on him!

Her version of the story completely twisted the truth:

She claimed the girl went home crying her eyes out, said they only grabbed a casual meal and shopped a little, and he randomly cut things off for no reason, branding him cheap, stingy, and lacking class.

7. His Mom Didn’t See His Side; He Lost All Motivation for Blind Dates

After hanging up with the matchmaker, his mom chewed him out without hearing his full side first: Spending a couple hundred bucks on a blind date is totally normal—why are you being so immature about this?

He finally snapped and said what every reasonable person was thinking:

This was never about the money—it’s about basic respect! She brought a random friend along to freeload food and drinks on our second one-on-one date, acted entitled to every single thing I paid for without a shred of gratitude or manners, and the second I turned her down, she ran to lie to everyone and paint herself as the wronged party.

Even after explaining every detail, his mom still wouldn’t understand and pressured him to reach out and apologize to win her back.

That was the breaking point for him: He’s done with blind dates forever.

8. All Online Readers Were Outraged by Her Behavior

Every person who read this story online sided with the guy and blasted the girl’s actions:

To show up to a blind date planning to freeload everything without spending a dime, then badmouth the guy as cheap once he refuses to keep footing all the bills.

Any normal guy would’ve ended things after that day, no questions asked.

Sincerity shouldn’t be drained and taken for granted, and kindness should never be treated like something you’re automatically owed.

Discussion Prompt

Do you think the guy was out of line for cutting the date off completely? Is it reasonable to bring a friend to freeload food and entertainment on the first proper one-on-one blind date?