Date night is supposed to be filled with romance and compassion for your SO. Unfortunately for these lovers, the night couldn't have turned out worse.
This Why You Should Drive Separately On The First Date
“After my freshman year of college, I met a guy on OKCupid. We went to get dinner at Friday’s as our first date. He offered to give me a ride, but I said no.
He was a couple years older, well dressed and started talking about how he’d started his own business after college and it was going well. Good for him! He was bragging a bit, but hey that’s an accomplishment.
So after we ordered, he said, ‘Let’s play a game – we’ll each take out our wallets and compare what’s in them.’ This wasn’t a joke. He literally started showing me his credit cards and bragging about the high limits. He ended with, ‘Clearly you can’t afford to pay for this dinner, but don’t worry I can cover you.’ I was so angry and protested, but he wouldn’t take no for an answer.
As we left, he said he wanted to show me his car. Unfortunately, it was before mine in the lot, so I had to walk by it. It was a white, windowless, serial killer van. He begged me to hook up with him in it, right there in the Friday’s parking lot.
I was pretty glad I drove separately.”
At Least The Servers Tried To Come To The Rescue
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“I met a guy from a dating site. In the photo, he sort of looked like Kevin Smith. I got to the restaurant and ordered a drink. I told the waiter I was meeting a blind date so make it a strong one.
The guy I met looks like Moe from The Three Stooges, but much thinner (same haircut and all). He proceeded to tell me that he lost all of the weight due to medical issues. I did not press further because we were having dinner and drinks.
He worked at a gaming store so he took off his work shirt and revealed a severely stained white undershirt. We are talking yellow pits to the max here. While talking about art, I noticed that he kept scratching his upper arm under the shirt sleeve. He asked if I wanted to see his tattoo. I said sure. When he lifted the sleeve, there was a cross tattoo, but his arm was COVERED in acne…which was what he was scratching and picking at.
We were at a Tex-Mex place. I ordered another drink and he ordered a meal. He told the waiter several times that he doesn’t want tomatoes. The meal came out and while talking, he used one of his too long fingernails to scratch the inside of his nose. He proceeded to clean the underside of his nail on the stack of napkins in the center of the table so his boogers were there for all to see.
When I thought I had enough liquid courage to run, the waiter came by and my date guy flipped out on him because he found a tomato in his con queso dip. He proceeds to say very loudly, ‘I CANNOT have tomatoes, dude, because I have irritable bowel syndrome!’ I wanted to die. Everyone was staring at us.
He excused himself to the bathroom shortly after and the waiter came flying over and said, ‘Hey, if you need to split, don’t worry, me and the girls will cover your drinks.’ I was so grateful, but I didn’t want to be mean, so I waited.
The waiter brought the check and ‘Moe,’ after patting his pants several times said, ‘Oh dang, I forgot my wallet. Let me borrow your cell and I will call my mom and tell her to grab it off my dresser and bring it.’ I don’t think I ever paid a check fast enough in my life.
After a day, he emailed asking when we could go out again. I told him I couldn’t and I didn’t feel like we clicked. He called me shallow.”
She Felt As If She Were On A Date With A Child
“About a year and a half ago, a guy from work asked me out. I had been his manager for a while and always considered him kinda cute. At the time, our company was going out of business, I was three months single, and there was no real reason to turn down his request for a date. I was a little nervous because this was my first time out after a 4-year relationship, but he seemed sweet.
The first red flag should have been that despite owning a car, he let his license expire because ‘driving scares him.’ So I drove an hour to his house, picked him up, and asked where we were going. He directed me to the nearest shopping mall.
I was thinking, ‘Okay, maybe we’re just going to go window shopping and grab a coffee and goof off. Kinda teenage but maybe I could use something less serious right now.’
We got there and the first thing he did was point out a sculpture that looked vaguely reminiscent of male private parts. Okay, I guess it’s silly that we seemed to be the only two shoppers who noticed it, but he kept laughing about it waaaaay after the humor died, he just kept pointing at it and laughing to himself.
Then he walked me straight to the corner of the mall where the Rainforest Cafe is.
We walked through the gift shop to where the host was standing and Guy immediately requested to be seated next to the animatronic gorillas. I must have given him a weird look because he turned to me and said, ‘They’re my favorite.’
We got seated next to a family of rubber gorillas that kept making awkward robotic motions which made him laugh, and at this point, I asked him if he planned on getting a drink, to which he replied yes. So I asked our waitress to bring me a mixed drink to sip before the food came out. He then asked the waitress if he was allowed to order off the children’s menu. She said yes. Next thing I knew, she was bringing back one mixed drink and one child’s plastic smoothie holder with a giant, cartoon orangutang head as a lid, from which a pink silly straw was protruding. It was filled with Coca-Cola.
‘I, uh, thought we were both getting a drink?’ I asked, feeling kind of sheepish because now I looked like I was a mother taking the son I apparently gave birth to at age two out to dinner.
‘Yeah, I don’t really like those kinds of drinks. And this came with a toy I wanted,’ he said, showing me that you can twist off the bottom of the cup and there’s a plastic monkey inside.
The rest of the meal was spent with him trying to convince me that we should tell the waitress it’s my birthday so we could get a free sundae with a sparkler on top because sparklers are so cool, and me using my napkin to casually wipe away tears of regret. Then I drove him home.”
She Eventually Found Out How He Could Afford The Expensive Dinner
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“A guy I knew through a few acquaintances asked me out on a date. He lived in Philly and I lived in Jersey at the time, about an hour away. I had nothing to do that night and he was kinda cute, so I thought I would go. What’s the worst that could happen? Awkward conversation and a free meal? I figured what the heck and I went.
I got down to Philly and picked him up at his place. He didn’t have a car so he apologized for making me drive. We went out to a super posh restaurant and had an amazing meal. I was about 19 at the time, so most of the dates I went on did not involve $200 meals, so I was basically floored with the baller status of this kid. No one had ever taken me out to a restaurant that fancy, except when my dad took our family out on Christmas Eve.
After we ate, he was like, ‘On the ride home, I just have to swing by my friend’s house, I just have to run in and drop something off. Do you mind? It’s right on the way. I’ll even drive your car there since you don’t know the city.’
For some reason, my dumb 19-year-old self agreed to this and let him drive my car. As we’re driving there, it’s plain to see that this neighborhood was totally sketchy. He pulled up in front of a run-down house and told me he’d be right back. I was sitting in the car freaking out at this point. He came back five minutes later, and said, ‘Here, hide this in your purse.’ He tossed a large baggie at me and inside there was a GIANT ball of crack. I’m talking the size of a softball here. Just at that moment, a police cruiser pulled up behind my car, obviously running my plates. I’m sure the cops figured the only reason a Jersey car would be in that section of Philly would be to score some kind of substance. My date drove off and the cops followed us for a few blocks and then, finally, turned off down another street. The entire time, my heart was in my throat. I just kept thinking about what my parents were going to say. I was a pretty good kid, never really messed around with anything illegal, so I was beyond scared.
We got back to his apartment, he took his giant crack rock and I went straight home back to Jersey. He called me for a second date. Needless to say, I didn’t go!”
“She’s Just Saying That Because She’s Poor”
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“In college, this guy from one of my classes asked me to go out with him out of the blue. We’d never even talked before, but he was pretty cute so I said sure. We exchanged numbers and he said he’d call me with details.
He called the next day and told me we were going to a restaurant that was WAY out of my price range. We’re talking like, no way this bill will be under $100. I tried talking him out of it, saying I couldn’t afford something like that, but he insisted and told me not to worry (this all really should have been a clue to me). So I said fine and agreed to go.
We got to the restaurant and the waiter came over. I went to order the cheapest thing on the menu but my date stopped me and said, ‘Ignore her, we’re both having the steak.’
‘But I don’t like steak,’ I protested.
He said, ‘She’s just saying that because she’s poor. We’ll have steak,’ and shooed the waiter away.
I was mortified, angry, and wanted to leave, but he was my ride. He tried to make conversation and just proved to me that he really was a prick. Then he said he had to go to the bathroom and left. I was sitting there for a good 10 minutes before he texted me, ‘Hahaha I got the runs from drinking last night, don’t eat without me.’
That was the last straw. I called the waiter over, paid for my meal, and went to the Starbucks down the street to call my friend to pick me up.”
She Used Her “Special Connection” To Get A Free Meal
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“A girl I had just met asked me out, she wanted to take me to dinner. We ended up at this little Italian place because she says she knows someone that works there.
When our waiter arrived, he appeared visibly shaken and started stuttering. She introduced me to him. This was the friend she’d mentioned before. I could see right away that this guy had a thing for her, and here she was introducing him to her date. She then bugged him for special orders and asked if we could get our meals free. He really seemed upset, but gave her the ‘anything for you’ look and agreed. I declined and paid for my own meal. I felt really bad for this guy, I could just see his torment at watching this girl date someone else. She was very attractive and very friendly. I assumed he just got friend-zoned. I hung out with her a few more times but backed off of the romantic part.
Later, I found out that the guy from the restaurant was her ex-boyfriend, who she had just dumped a few days before and had been dating since high school.”
The Craziest BBQ That Never Happened
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“Years ago, my friend called me up and said, ‘Hey, I’ve got a friend who needs a date tonight! She’s really cute and funny. She’s going to a BBQ but her ex-BF is gonna be there and she just wants a good guy on her arm to make sure he doesn’t try to bother her.’ Given that I hadn’t had a decent date in months and it seemed like the nice thing to do, foolish, foolish me decided to say yes.
She showed up and picked me up in her car to take me to the BBQ. We made small talk and I learned she was a high school dropout. I value intelligence in a date but hey, I know that these things happen so I tried to withhold judgement. Also, she was pretty cute, which didn’t hurt.
We drove out into the middle of the suburbs and got out of her car to go to the BBQ. Turns out that we were the first ones there, which, okay fine, I like to be early. The only people in the house were the hostess, whom I shall call Mrs. Crazy, the host (Mr. Crazy), the hostesses’ grandpa (Old Crazy), and their toddler, Crazy Jr.
Trouble began immediately because we were not followed outside to the backyard. A glance through the window showed that there was no BBQ grill set up whatsoever. I shrugged this off as it still being early. I tried to make small talk and politely asked Mrs. Crazy if she knew my friend who’d set me up on this blind date with this girl.
Mrs. Crazy responded venomously, ‘Do you mean the guy who got me sent TO PRISON and caused me to ALMOST LOSE MY BABY?!?’
‘Uh,’ I replied in shock. Turns out that my idiot friend reported her for stealing from his job and while she was in lock-up for the night, she had gotten into a fight with another lady inmate. My date then took Mrs. Crazy aside and they had a conversation. It was decided that I was allowed to stay as my date convinced her it wasn’t my fault that my friend got her arrested for stealing. Hooray?
A half-hour passed uncomfortably and I asked what they’ll be grilling today. Mr. Crazy blinked and said, ‘Oh, yeah, I guess we should go outside.’
So we headed outside. Everyone sat down…including Mr. Crazy. Crazy Jr. got up and waddled around the backyard in a poop-filled diaper as Old Crazy mumbled to himself in a chair. Everyone else was still seated. I looked at Mr. Crazy, looked around for a grill, then looked back at Mr. Crazy.
‘So, when are the other guests arriving?’ I asked politely.
‘I dunno. Soon, probably. We should wait for them,’ replied Mr. Crazy with a shrug.
I glanced over at my date, who smiled apologetically. I just nodded and smiled at Mr. Crazy, as I was raised with good manners and began patiently awaiting the other guests.
Flash forward two freaking hours. Nobody else had shown up. Mr. and Mrs. Crazy show no signs of this being odd or of any urge to cook and grill meat. Eventually, they and my date meandered back inside. I stayed outside with Crazy Jr., still waddling around the backyard in his own feces. His supposed guardian, Old Crazy and I were getting pretty angry at this situation. I was hungry and there was no food, just nasty drinks which I wouldn’t drink on a full stomach, much less an empty one.
Eventually, I went inside to find my date, Mrs. Crazy and Mr. Crazy talking. I asked my date as politely as I could if she thought her ex-BF would show up with a strong hint that I actually meant, ‘IS ANYBODY GOING TO SHOW UP TO THIS SHAM OF A BBQ?’
She just shrugged. ‘Maybe.’
It had been almost three hours now with no food in the home of somebody who hated one of my friends. I was now stuck in the suburbs with no idea how to get home. I didn’t have money for a cab or know the address (my phone wasn’t a smartphone back then). At this point, I insinuated that I REALLY should be going.
My date pouted and said, ‘No, no, don’t leave! We can play games!’
I counted to ten in my head and thought, ‘Fine, we’ll play some Scattergories or something and then I can finally leave this awkward place. Maybe, now that it is abundantly clear that nobody is showing up, they may even cook and grill me some meat or at least a freaking hot dog.’
As I followed them downstairs into their rec room/basement (God only knows what happens to Old Crazy and Crazy Jr. after this point), I loudly asked Mr. Crazy if he was going to BBQ anything tonight.
‘Oh, yeah, food,’ he said. Seriously, that was his exact phrasing. ‘I’ll go cook something up. Mrs. Crazy, you get everyone started.’
Mrs. Crazy got me and my date seated on a couch and then asked me a question, ‘Have you ever played Dungeons and Dragons before?’
I stare at her. At this point in my life, I’d never Tabletop RPG’d and the idea of doing so with this group sounded about as appealing as dental surgery.
‘No,’ I told her in my least enthused tone of voice, ‘Never.’
She didn’t get the hint and instead said, ‘You’re going to be in for a treat! Mr. Crazy’s an awesome Dungeon Master!’
She handed me a freaking tome the size of a textbook and I stared at it dumbly. This was definitely not freaking Scattergories.
Mrs. Crazy handed me some dice and started to explain the rules, most of which I ignored as I was staring at my date and trying to communicate with just my face that I was freaking done. Time to leave. Now. In fact, the time to leave was three hours ago. My date, however, was too enamored of the magical freaking adventure we were apparently about to embark on to even care about me anymore.
Finally, the kicker – I heard Mr. Crazy coming downstairs. Thank God, I thought. At least this terrible, TERRIBLE date would have some kind of food as I was starving. I was so hungry at this point that I thought I’d eat anything, no matter if he charred it or just handed me a hot dog with no bun. But no, he didn’t bring down BBQ, burgers or hot dogs – he brought down a big plate of fish sticks.
Half-cooked, room temperature freaking fish sticks.
And the worst part? I was so hungry, I ate five of them before the taste made me feel sick. I was shoveling these rancid half-cooked pieces of fish in my face as he was asking me what character class was I, what race was I, and so on. I ended up giving him random answers and ended up being a goblin werewolf warrior or some other random nonsense. I don’t even remember. All I was really thinking was, ‘God, these are totally disgusting…but I’m so hungry…I want to go home right now,’ on a loop.
He tried to start our magical adventure into IDontCareArnia but I told him I needed to use the bathroom, half-tempted to immediately puke up the half-cooked fish sticks I just ate. I ran into their bathroom and heard either Old Crazy or Crazy Jr. crying in the distance. I locked the door and proceeded to text everyone I knew with a car who was free that evening to COME GET ME. I figured I’d just leave quietly and walk to the nearest intersection I could find where I could give them directions. I contemplated texting my dear, sweet friend who set me up about exactly how much FUN I was having but decided that I need to scream at him in person about this night instead.
Nobody got back to me. I was lost and abandoned in this suburban prison. With reluctance and growing nausea, I headed back downstairs.
As the game began, I responded only in noncommittal grunts and single syllable words, glaring at my date as if to say, ‘I WANT TO LEAVE NOW.’ I fake yawned several times. I stared at my watch repeatedly. Nobody was taking the freaking subtle hints. They were too enraptured by Mr. Crazy DM’s droning description of thatch huts and orc corpses or whatever.
Finally, I just took my phone out and openly started scrolling through my texts, desperately hoping that someone with a car had gotten back to me. I muttered, ‘C’mon, Ryan!’ just loud enough that Mrs. Crazy heard me.
‘Did you say…Ryan?’ she said with a familiar tone in her voice. I prepared myself for the worst – somehow my other friend set her house on fire and killed her parents or something. That’s about how this night has gone so far.
‘Yeah,’ I replied warily. ‘Why?’
‘Oh, I knew this guy named Ryan in high school,’ she says with obvious disgust. ‘Everyone said he blew some guy under the bleachers. Totally gay.’
Suddenly, I saw my only way out of here. I had been afraid of inciting the wrath of Mrs. Crazy, but now I saw that my only hope to leave this garbage dump was to deliberately anger this homophobic, thieving witch. At this point, it would be the only real pleasure I derived from the entire evening.
‘I never heard that about Ryan, but he and I have been friends for YEARS! And he IS gay. Totally gay! GREAT guy!’ I announced with a big grin on my face. ‘We hang out ALL THE TIME!’
Mrs. Crazy faked a smile and got up to whisper in Mr. Crazy’s ear. Mr. Crazy was dismayed to be dragged away from his DMing duties, but they went to another room. Miracle of miracles, they finally came out and said to my date that they were having SO much FUN, but they’re both really tired and that we should probably go.
I held back a sigh of relief and a loud praising of God before nodding and running up the stairs without so much as a good-bye. Eventually, my date came up as well and saw me standing by the door and glaring at her. She drove me home in near total silence and I pointedly did not ask if I could see her again or try for so much as a hug. I slammed the door as I got out of her car and stalked back up into my house.
Five minutes later, my friend called me.
‘So, how’d it go?’ he asked me excitedly.
I hung up on him and don’t talk to him for three days, which is the amount of time it takes my anger to lower from ‘strangle you’ levels to ‘yell at you’ levels.
I have never been on another blind date since and never will again.”
Getting Through This Date Was ‘Ruff’
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“There’s been a few but the absolute worst was the woman who turned up at the pub with literally no money, expecting me to buy her drinks and dinner. I wouldn’t have minded if she’d have told me beforehand but this was completely out of the blue.
So anyway, we sat there making awkward conversation, or at least I tried to start a conversation, told her about my life, asked her questions. She was too busy texting and phoning her friends to really take notice.
Eventually, we did get talking, then out of nowhere, she told me that she killed her dog. Not accidentally, either.
I just up and left and avoided all contact.”
“Even Attractive People Can Be A Bag Of Crazy”
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“I went on a few dates with a guy in college. At first, I was excited because I found him attractive and he said yes to a dinner date. Turns out, even attractive people can be a bag of crazy.
For our first date, we went out to an Italian restaurant. He ordered spaghetti with regular sauce, no meatballs. Out of curiosity, I asked if he’d tried anything else on the menu that he would recommend. He said, ‘Nope, I only ever order spaghetti.’
When the food came, he proceeded to lean over his plate, shovel the spaghetti in his mouth, and use his lips to cut the rest back on his plate. I’m no snob, I’ve eaten spaghetti like that before, just never in public. He said it’s the right way to eat it.
He asked if I’d like to go see a movie, but I wasn’t feeling the vibe so I declined and made up some project I had to finish. He told me he loves the movies and wishes he could just live in one all the time.
Uhm, alright, well, thanks for the date…
A week later, he asked me out again. I decided to give him another shot. Maybe I was being overly judgmental or petty. We agreed to go out for pizza and see a movie.
I picked him up at his house and we went to Pizza Hut at his insistence. ‘It’s the best pizza on the planet,’ he told me about three times on the way there. We got there and he ordered a personal pan for himself. That was a first. Maybe he didn’t want to share the bill? I ordered one for myself and just let it go. Again, I was worrying that maybe I was being judgy. I was really confused when the bill came and he paid, but whatever, I’m not going to call him out, not worth it.
The ‘movie’ ended up being back at his house where (surprise!) he lived with his parents. His dad asked me what I’m in school for and when I told him, he lectured me that I should go to school for teaching, since that’s what he does, which I thought was rude.
We never did watch the movie. Instead, we spent the rest of the evening with him showing me all his WWF wrestling memorabilia and bossing his mother around, Cartman style. His life goal was to get his old job at Blockbuster back since it was the most fun he’d ever had. His favorite way to spend Christmas was when his mom let him open everything the night before so he could spend the day at the movies, avoiding all the relatives that came over for Christmas dinner. He hated everything his mother cooked and counted off to me the only ten foods he would ever eat; he hated everything else, didn’t need to even try it.
Did I mention he was 27 years old?
A few days later, he invited me out to coffee and I agreed so I could tell him I won’t be going on any more dates with him. He was nice enough and even though he was an oddball, we never got each other to laugh. All our conversations were dry, no shared interests, and he didn’t have the same values on the importance of family. This wasn’t going to work.
We met up and he ordered a meal while I got coffee. I told him that I enjoyed our dates, but wouldn’t be seeing him again. He yelled, ‘So you’re breaking up with me?!’ We weren’t anything official.
‘I can’t believe you’re dumping me!’ Then he stormed out, leaving his food behind half eaten. I sat there for a few moments kind of stunned, slightly amused, but okay, life goes on.
A few weeks went by and now it’s the holidays. I ran into him again and this time we did hit it off. He seemed to laugh easier, told good jokes, etc. He asked what I was doing for New Years and I invited him to the party I was going to. I figured maybe we could at least be friends. I told him about the other girls that would be there and he seemed to get the hint that we weren’t going as a couple.
We got to the party and he loudly declared that he doesn’t drink. That’s fine, no one reacted, no biggie. He sat in the corner refusing to acknowledge anyone. He seemed upset for some reason so I asked him what’s wrong. He was upset because the movie trivia game we were playing earlier had a mistake in it. I told him, ‘Uhm, alright, well…we’ll get the info off the box and write to them.’ He seemed to cheer up after this.
Later, he snuck into the kitchen and began to prepare himself a ‘mixed’ drink by pouring a little of everything into a glass. He didn’t notice me. He was talking to himself going, ‘Yeah a little of this, oooh maybe some of that.’ He took a sip of his drink with a splash of tap water and poured the rest down the drain. I don’t think he wanted to admit he didn’t know how mixing drinks worked.
On the drive home the next morning, he pretended to have a hangover and didn’t talk much. I was driving and the roads were icy, so I didn’t mind the silence. With about 30 minutes left on the trip, he asked me what I wanted to do with my college degree. I told him my plans and stuff I’m excited to do. He then said, ‘I don’t see the point of you wasting your time getting a degree. You’ll just be spending the rest of your life raising my children and cooking me meals that I like.’
It took all I had not to dump him off right there on the freeway. He continued to say demeaning nonsense about our future, how he’ll convince me to drop out of college, how pointless it is for all women to get degrees, blah blah blah. My ears began ringing with rage. I’d never had someone say anything so outrightly unsupportive like that to my face. I knew he had some strange social issues, maybe some anxiety about trying new things, but this was too much. I calmly told him I was not going to be told my lot in life is to raise his babies on his part-time Blockbuster paycheck. I didn’t say another word to him, just dropped him off at his car and drove off.
I did learn to never feel obligated to put up with someone’s stuff. I kept giving him chances when I shouldn’t have but in the end, I think I needed to learn that lesson. Now I’m really careful about not leading men on, especially if they have poor social skills.”
You Can Always Judge A Person’s Character By How They Treat Their Server
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“I’m impressed and entertained pretty easily. It takes a lot for me to have a bad date or ‘judge’ anyone.
I went on a date with quite a rich guy about a year ago. He was nice, fit, handsome, well educated and well dressed. Basically everything a girl would ‘want.’ To be honest, I only went on the date because I loved how he spoke.
Anyway.
We had a nice time, I guess. However, the whole time he spoke about himself. Or tried to impress me in some way. To the point where we went to a sports store and he ‘casually’ bench pressed and whatever in front of me, claiming he wanted to ‘test it out.’
He spoke about buying expensive beverages and whatnot – and don’t get me wrong, I love a nice bottle, but I had literally gotten sloshed off of Franzia the day before with friends. I’m not picky and he talked about drinking $100 bottles nightly. Idiot.
The last straw was going to a sweet, independent café. They got the order mixed up by a tiny detail, and he huffed like the biggest pompous prick. ‘I’m never coming HERE again.’
I was like, ‘Forget you, man. I don’t care if your family owns half of this city, but treat cafés and their waitresses with respect. People mess up. Why not spend your nightly $100 for vino on lessons on how to not be a spoiled little wanker instead.’
He then wrote a blog about how I was his muse. I never spoke to him again.”