dating

Dating is a tricky place. Whether it's online, blind, or a witty pick up line at the bar, the ways to start that dance are nearly endless. Unfortunately, some people still don't manage to navigate its nuances, and end up a lesson what not to do.

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‘I’ve got three brunch invites next month and someone offered to fly me to Aspen’: Woman introduces two bored rich kids at a fundraiser, they click immediately, and their parents decide she’s now a matchmaker for the elite

‘I’ve got three brunch invites next month and someone offered to fly me to Aspen’: Woman introduces two bored rich kids at a fundraiser, they click immediately, and their parents decide she’s now a matchmaker for the elite

‘I took off the ring, told him it was over, and that he needed to move out’: 37-year-old Tom demands his rich fiancée buy a bigger house and put it 50-50 in both names, drops a take-it-or-leave-it ultimatum, and immediately regrets it

‘I took off the ring, told him it was over, and that he needed to move out’: 37-year-old Tom demands his rich fiancée buy a bigger house and put it 50-50 in both names, drops a take-it-or-leave-it ultimatum, and immediately regrets it

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‘You’re doing the best you can mom and dad!': Parenting laughs and woes for witty mothers and fathers

‘You’re doing the best you can mom and dad!': Parenting laughs and woes for witty mothers and fathers (September 13, 2025)

‘I have my own bills and credit card debts to pay’: 33-year-old woman refuses to cover her 38-year-old boyfriend’s full bills after five months of “no prospect in sight” post‑graduation job search

‘I have my own bills and credit card debts to pay’: 33-year-old woman refuses to cover her 38-year-old boyfriend’s full bills after five months of “no prospect in sight” post‑graduation job search

‘She made me feel like the villain for respecting her wishes’: 29-year-old scolds her 32-year-old boyfriend for skipping a 3 a.m. airport pickup she repeatedly refused and even bought a bus ticket for

‘She made me feel like the villain for respecting her wishes’: 29-year-old scolds her 32-year-old boyfriend for skipping a 3 a.m. airport pickup she repeatedly refused and even bought a bus ticket for

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‘She messaged me angrily, saying that because of me, people judge her’: 19-year-old vents about a tough breakup to a friend, the story spreads, and his ex complains about the backlash

‘She messaged me angrily, saying that because of me, people judge her’: 19-year-old vents about a tough breakup to a friend, the story spreads, and his ex complains about the backlash

relationships, boyfriend, girlfriend, work, performance review, dating, argument, aio, reddit, reddit thread

33-year-old demands girlfriend submit to workplace-style performance reviews, gets frustrated when she refuses: 'He insists this will make us stronger as a team'

Boyfriend refuses his girlfriend’s demand he buy a house under her name only, offers joint ownership instead and triggers accusations that reveal trust issues: ‘‘She told me only putting her name would make her feel safe’

Boyfriend refuses his girlfriend’s demand he buy a house under her name only, offers joint ownership instead and triggers accusations that reveal trust issues: ‘‘She told me only putting her name would make her feel safe’

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Dating Relationships, boyfriend, dating fails, gifts, presents, present, bracelet, dates, bracelets, girlfriend, breakup, money, dating, breakups, dating advice, overreaction

25-year-old breaks up with his girlfriend of 8 months because she didn't love the $1300 tennis bracelet he bought her: 'She didn't appreciate how much it meant to me to give her something special.'

‘Yearning is so back’: Posts that make a heart full of woes laugh

‘Yearning is so back’: Posts that make a heart full of woes laugh

'My close personal bestie just got engaged...': Fan reactions and posts of Taylor Swift and Travis Kelce that are making us all laugh and smile

'My close personal bestie just got engaged...': Fan reactions and posts of Taylor Swift and Travis Kelce that are making us all laugh and smile

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Woman cuts power and serves eviction papers to her ex after 18 months of freeloading and refusal to leave her house: ‘Boy, sit down. Your karma is already serving’

Woman cuts power and serves eviction papers to her ex after 18 months of freeloading and refusal to leave her house: ‘Boy, sit down. Your karma is already serving’

venmo, dating fails, sharing, bad date, bad dates, french fries, reddit story, pay back, fries, dinner, food, reddit thread, Reddit, payback, money, dating, money problems

30-year-old guy asks 28-year-old woman he took on a 1st date to pay him back $3.25 for the fries they ate, date refuses to pay it: 'He said it’s about fairness and that’s just how he is.'

‘a personal chef, maid and babysitter who still pays half the bills!’: 48-year-old single man describes his unrealistic expectations from a partner, neatly exposing his lifelong bachelor status

‘A personal chef, maid and babysitter who still pays half the bills!’: 48-year-old single man describes his unrealistic expectations from a partner, neatly exposing his lifelong bachelor status

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Woman kicked out of hotel by friend Anna and her fling Ben on her own birthday trip, ends up alone in a hostel, and decides to cut ties: ‘She just carried on with her plans’

Woman kicked out of hotel by friend Anna and her fling Ben on her own birthday trip, ends up alone in a hostel, and decides to cut ties: ‘She just carried on with her plans’

‘I even wore a suit’: Ex tries one last time to get back together with his girlfriend by presenting a professional PowerPoint, makes her father cry instead, does not reunite

‘I even wore a suit’: Ex tries one last time to get back together with his girlfriend by presenting a professional PowerPoint, makes her father cry instead, does not reunite