c/bad-date-diaries

Wasted $180 on a speed dating event in Chicago, total circus

I paid $180 for a 'premium' speed dating night last Friday and it was a total mess. They crammed 30 people into a tiny bar, we got 3 minutes per chat, and half the guys were just there to push their crypto side hustle. I made zero connections and the 'free' drinks were flat soda. Has anyone else dropped big cash on one of these events and ended up regretting it hard?

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martin.paige•1d ago

Split the bill or let him pay? The $180 dinner that turned into a fight

Met this guy from an app at a sushi place downtown. He picked the spot, ordered two rounds of sake, got the deluxe platter. Check comes and he just stares at it. Then he says "you got the next one right?" I said no, I thought you were covering since you picked everything. He goes off about how it's 2025 and women need to split. I paid my half, left, blocked him. But now I'm wondering, is splitting always the rule now, or is it still okay to expect the person who does the inviting to pay? Did I dodge a cheapskate or was I out of line?

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the_charlie•1d ago

My coworker's 'wait three days' advice ruined my best shot at a second date

So last month I met this really cool woman at a coffee shop in Portland, we talked for like an hour and she gave me her number. I told my coworker Dana about it, and she swore I had to wait exactly three days before texting, something about playing hard to get or whatever. I followed her advice, sent a casual 'hey, how's your week going?' on day three, and got a one word response. Then nothing. I ran into her at that same coffee shop last Tuesday and she said she figured I wasn't interested since I took so long, and she'd already started seeing someone else. Dana meant well but her rule cost me a real connection. Has anyone else had their friends' dating advice backfire this badly, and what do you actually do when a genuine spark happens but you're told to hold back?

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zarab24•2d ago

I finally realized what my last date was really telling me at dinner

She spent 20 minutes talking about her ex's landscaping business, how he "trimmed trees wrong" and I just nodded along. Then it hit me, she was testing if I'd call out bad work or let it slide. Has anyone else picked up on a date's hidden test like that, or am I reading too much into stuff?

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elizabeth900•8d ago

Third date win: he asked before touching my hand, gasp

Honestly after 12 bad dates this year, I thought chivalry was dead. But this guy from Philly actually asked permission before holding my hand at the movie theater, and it felt huge. Everyone on here talks about red flags, but what about green ones like this? Has anyone else had a small gesture make them rethink their whole dating bar?

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the_margaret•9d ago

Just realized I was the problem on my last date, not him

I went out with a guy from work last Friday at a diner in Akron. He ordered the meatloaf special and started telling me about his coin collection, and I kept checking my watch and interrupting to talk about my own day. Then the waitress brought him the wrong pie and he just shrugged and said 'no worries, I like cherry better anyway,' and it hit me that I'd been sulky and rude for 45 minutes straight. I apologized right there, we split the $32 check, and ended up talking for another hour. Has anyone else had that moment where you realize the bad date was mostly you?

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reesemiller•9d ago

The pre-date phone call trick I stumbled on after my 14th disaster

So after years of getting stood up or sitting through painfully awkward dinners, I realized something. Almost every bad date I had, we only texted before meeting up. Then this one time, this girl called me out of the blue to confirm the time, and we ended up talking for 20 minutes. The actual date went way smoother because we already had a rhythm. Now I just call anyone before a first date, even if it feels weird. Worst case, they don't answer and I know to lower my expectations. Has anyone else tried this or am I just old fashioned now?

1 comments

taylor_hayes25•12d ago

Paid $70 for a matchmaking service and it was actually worth it

I got ghosted three times in a row back in March, so I signed up for this local matchmaking thing in Boise out of spite. For $70 they set me up with one in-person coffee date, which felt steep for a gamble. The woman they paired me with was someone I never would have swiped on, and we ended up talking for 3 hours about dumpster diving mishaps. She wasn't my person, but she gave me a blunt read on my dating profile photos that saved me from more dead ends. I swore off paying for dating stuff after a $200 dinner disaster last year, but this one actually paid for itself. Has anyone else tried those cheap matchmaking setups, or is this a one-off fluke?

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piper912•12d ago

That $45 'nice dinner' try cost me more than the check

Went out with this guy last Tuesday who insisted we do a fancy place, he even picked the spot. I spent $45 on a dress I didn't need because his photos showed a suit and I figured I should match, you know how it is. He showed up in jeans and a hoodie, then spent the whole meal talking about his ex's dog like it was a therapy session. The bill came and he slid it to me saying he forgot his wallet, so I ate the $120 total too. That dress is still in my closet with the tags on, and the only thing I actually learned is to ask for a video call before agreeing to a pricey venue. Has anyone else dropped cash on prep for a date that went sideways, or am I just the clown here?

1 comments

carr.brooke•16d ago

Paid $65 for a dating coach, got told to 'just be myself'

After three busted relationships in a row, I shelled out $65 for a 30 minute video call with a so called dating coach in Austin. She asked about my hobbies, I said hiking and cooking, and she nodded like she'd cracked a code. Then she literally told me to 'just be yourself and stop trying so hard.' That was it. No tips on how to talk to people, no feedback on my profile, just a bill for words I could've gotten from a fortune cookie. I get that dating advice is often common sense, but I paid for strategy, not a motivational poster. Has anyone else dropped cash on dating help that was pure fluff, or did you actually get something useful?

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nancy524•17d ago

Ghosted after 4 dates, then they texted 6 months later like nothing happened

Honestly, I need opinions on this because I keep going back and forth. I saw this guy from Bumble for a month, four solid dates around Austin, we even talked about a trip to Fredericksburg. Then he just vanished, no text, no explanation, nothing. I was annoyed but moved on, deleted his number. Fast forward six months, he sends me a random message saying 'hey stranger, how's your summer?' like we were just busy. Part of me wants to reply and ask what the hell happened, but the other part thinks that's just giving them a second chance to waste my time again. Is it worth calling someone out for ghosting after all that time, or is silence the only real answer? Has anyone else had a ghost resurface and actually gotten a good explanation, or was it always just the same flaky energy again?

1 comments

charlienelson•17d ago

Took 4 months to realize my date's 'busy season' was permanent

Met a guy on Hinge back in March who swore his job as a night manager meant he could only see me on Tuesdays, so I rearranged my whole schedule around 4 dates a month. Then I found out from his coworker at a bar in Austin that he'd been saying that to everyone for two years just to dodge commitment. Why do we give people this much benefit of the doubt when the first red flag is staring us right in the face? Anyone else burned six weeks or more on a schedule that was never going to open up?

1 comments

verar21•19d ago

Split the check or let him pay? My broke date taught me a lesson

I went out with this guy last Friday in Chicago, and when the bill came he just stared at it. I offered to split, he said no, then asked me to Venmo him $40 because he forgot his wallet. Do I call that cheap or just honest? Has anyone else dealt with the awkward money dance, and what's the better move?

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alice_kim•22d ago

I finally stopped giving out my real number on apps

Used to hand my actual cell number to every match that seemed decent, and one guy in Denver texted me 47 times after a single coffee meet. Now I use a Google Voice line for the first three dates, and if they pass the vibe check, they get the real digits. The shift happened after that guy found my apartment building through my number and left a note on my car. Has anyone else had a stalker situation escalate that fast, or am I just unlucky?

1 comments

elliot45•23d ago

That $60 cooking class I booked before a date: total flop or weird icebreaker?

Spent $60 on a couples pasta-making class for a first date and she ended up loving the chef's jokes more than my dough skills, but would I have been better off just grabbing $20 tacos, what do you all think?

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paul346•24d ago

Dude quoted his ex's review of him on our first date

Met a guy from Hinge at a coffee shop in Austin last Saturday and 20 minutes in he pulls out his phone to read me a 2-star Yelp-style review his ex wrote about his dating habits. He was laughing like it was a comedy bit, but the review called him out for never asking follow-up questions and checking his watch during dinner. I sat there wondering if I should take notes or run, so has anyone else had someone audition for them using their ex's complaints?

2 comments

oscarb77•24d ago

So I fixed a date invite mishap that took 2 weeks to straighten out

Okay so last month I matched with this girl on Hinge and we set up a coffee date for a Tuesday. I showed up at the right spot but wrong location, there are two 'Ground Up' cafes in Austin and I picked the one on 5th instead of the one on Lamar. She waited 20 minutes and left, then I spent like two weeks texting back and forth trying to explain and re-plan. That was way more effort than the date itself wouldve been, and we finally met last Friday. Has anyone else had a mixup that turned into a whole project before you even got to the bad part?

2 comments

elizabethn56•26d ago

I think splitting the bill on a first date is totally fine

Met someone at The Broken Egg in Nashville last Saturday and when the check came she just stared at me. I said let's split it and she got all quiet. I don't get why people act like the guy has to pay for everything, it's 2024 and we both have jobs. Has anyone else had a date get weird over splitting?

4 comments

mila_perry13•27d ago

Debate: Do you split the bill 50/50 on a first date or let the person who asked pay?

Heard two friends arguing about this at a coffee shop yesterday. One said splitting shows independence and avoids awkwardness. The other said it kills the romantic vibe and makes it feel like a business meeting. I got asked out for drinks last Wednesday and the guy insisted on paying but I felt weird about it lol. What do you all think? Has anyone had a date go sour because of how the check was handled?

2 comments

gibson.elizabeth•1mo ago

My friend's 'three date rule' advice nearly got me ghosted

Honestly, my buddy Mark told me to always wait three dates before texting back after a good first date. Tbh, I tried it with this girl from Hinge, and after two days of silence, she messaged me saying 'guess this isn't happening then.' I had to scramble to explain I was just following dumb advice, and she laughed but said it almost killed the vibe. Has anyone else had a friend's dating 'rule' totally backfire on them?

2 comments

dianas50•1mo ago

Hit my 50th first date last week and it was a total flop

I've been keeping a tally for the past 3 years and finally reached 50 first dates. Number 50 showed up in ripped jeans and spent the whole night talking about his ex's cat... Has anyone else hit a weird milestone like this and felt kinda bummed about it?

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phoenix_carter•1mo ago

Tried letting the other person pick the restaurant on a first date. Big mistake.

She chose a place called "The Clam Shack" that had a 45 minute wait and smelled like old fish. Then she ordered a salad and complained about the price of everything. Has anyone else had a date's restaurant choice tell you everything you needed to know upfront?

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the_piper•1mo ago

Shoutout to the $200 dinner that ruined my dating budget for a month

So I went on this date last week in Austin and the girl insisted on a fancy steakhouse. I told her upfront I was on a budget, but she kept ordering expensive apps and a pricey bottle of wine. The bill came to $210 including tip, and she didn't offer to split once. On the flip side, I have a friend who always does coffee dates for under $15 and says it filters out the high-maintenance people fast. Which approach actually works better for you guys? Is spending big upfront a red flag or just part of modern dating?

2 comments

simonl11•1mo ago

That dating statistic about 30 percent of first dates not leading to a second one really hit me different

I read this piece on a dating blog last week that said about 30% of people never get a second date because they talk too much about their ex. I always thought I was fine on dates but then I counted back and realized I mentioned my ex in 3 out of my last 5 dates. No wonder I kept getting ghosted. Has anyone else actually kept track of what they talk about and noticed a pattern?

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thomas.tyler•1mo ago

Matched with a guy who showed up 45 minutes late and blamed it on 'traffic' even though he lives 10 minutes away

I waited at the coffee shop in downtown Portland for almost an hour, watching my latte go cold and my patience run out. When he finally rolled in, he didn't even apologize, just said 'traffic was wild' with a straight face. How do you even respond to that without just walking out?

2 comments