Sometimes dating can be fun. But often, it can be awkward, expensive, and not worth the time. The following stories reveal just how bad the dating pool can be. I'm certainly glad I wasn't on these dates! Some content has been edited for clarity.
Date gone wrong — Content has been edited for clarity.
She Went A Little Too Hard
“So I’m living in the Bay Area, working as a management consultant, and I buy a new car. I’m a bit of a performance enthusiast, so it was a nice one but nothing too ostentatious, but it was at a nice dealership.
In buying cars, you often deal with the service counter, and at that service counter was a painfully cute brunette. So, of course, I make sure that I get everything done that I needed to and struck up a conversation during one visit. Talked a bit and asked her if she wanted to hang out sometime. She agreed, said it sounded fun. We exchange info, I agree to pick her up later that week. Tell her it’s a casual date, fun, nothing formal.
So, I pick her up, her roommate answers the door and says Lelia is running a little late, to come in and wait, shouldn’t be long.
45 minutes later, Lelia comes out, but she’s looking good, so I’m not too angry. But lord, 45 minutes late for a casual date, but okay.
So we go to a mini-golf place, a nice one, and we play a little bit. She’s cute but annoying. She was a screamer, and that is one thing that rides my nerve. When a woman screams at every little thing, just random shrieks because ‘it’s fun’. She misses close, she screams, she sinks one, she screams, something happens with a hazard, she screams.
We’re talking, and there is a difference in educational levels and interests. Career goals are a bit different. That kind of thing. She’s also younger than I am by a few years. I was like 26 at that time, I think, she was probably 22. So different levels of maturity. But it’s not a total disaster yet, I’m just mildly annoyed, but being nice.
About halfway through the game, she orders a drink. No big deal, I order one too. Then she orders another at the end of the game. I tell her that I was thinking a nearby restaurant that’s pretty good, she agrees. We head over there.
We walk in, and she exclaims, ‘Let’s sit at the bar!’ Okay, let’s do that.
I will say, that anytime your date, when you’re in a sort of trendy place, yells ‘Shots!’ It’s a bad sign.
I order some appetizers, she orders a mixed drink. Which by the time the food arrives, has turned into shots. I’ve tried to tell her to back off the drinking, slow down, all that stuff. She says I don’t know how to have a good time.
Suffice it to say, she gets hammered.
Hammered enough to be obnoxious with the server, and generally look like a fool. At one point she gets up to use the restroom and loudly exclaims:
‘Gotta break the seal!’ Followed by a ‘woo-hoo’ sound.
To which people all look at. Understand that this isn’t a party bar or restaurant. It’s sort of a cool place with craft drinks and decent food. I wanted to burst into flames. One woman at the table over looks at me and says, ‘I’m so sorry’ and her [presumed boyfriend/husband] goes, ‘ouch, dude, cut and run.’ Do you have any idea how embarrassing someone has to be to bring people into commenting on your terrible date? Pretty freaking embarrassing.
She left her phone on the table, and I had to. I picked it up, it wasn’t locked. Found her roommates number and called her. Told her this was Richard, Lelia’s date, and she was plastered. Utterly ridiculous.
‘Yeah, that happens, she likes to have a good time. Just bring her home, I guess. It’s gonna get worse.’
Lelia comes out of the bathroom, still reeling, and stops our server and says, ‘I wanna ‘nother shot.’ I’m like ‘No, we need to get going.’ She then calls me a ‘wuss’ and that I’m uptight. I lead her out, drop about $120 on the table knowing that will cover with a generous tip and lead her out of the restaurant.
We get going, she wants to ‘Hit a bar and party’ and I want nothing of the sort. She says, ‘Oh we could go back your place.’ and makes this weird hip-gyrating motion with a sound I can only describe as ‘eh-eh-ehhh.’
No, not happening. One, I’m not going to sleep with some inebriated girl. Two, I don’t want this crazy person in my rather nice apartment. I tell her I’m taking her home. She gets angry, calls me a ‘baby’ and that I don’t know how to have fun.
Then she says she doesn’t feel so good, to which I pull over and was about to help her out, and she says ‘It’s coming’ and I roll down the window, and she hangs out and proceeds to upchuck down the outside of my car. My brand-new IS-F. I wasn’t amused. At this point, I’m past being polite. I open the door for her, she finishes giving flight to her dinner. I get her back in the car and drive her home.
She starts crying and saying what a wreck she is. I agree with that. As I said, I’m past being polite. She starts crying more, and I bite my lip and drive her home without saying another word. I’m mad. I mean, angry.
I take her up to her place, as she stumbles and cries, not letting her fall and knock on her door. Her roommate answers and takes her inside. Apologizes, and Lelia turns around and says something incomprehensible. I make my escape.
Then find a car wash and find myself washing vomit off of my car in the dark, alone.
That was an interesting of a moment.
Still, by far the worst date I’ve ever been on.”
Never Drive To Him
“When eHarmony first came out I decided to give it a try. I was matched with a gentleman who lived about 25 miles from me. On the day of our date, that ended up being a 2 hour drive in traffic. Yes, he asked if I would come to him.
When I got to his place he asked me to come inside and see his aquarium. I went inside to find a house with no furniture and a piranha tank in the corner. I watched this guy feed his piranhas, then against my better judgement, we set off on the world’s worst date. He offered to drive, but 5 minutes from his home, he announced we had to go get his car washed, since it was his little sister’s graduation the next day and he didn’t want to ‘roll up in a filthy car.’
I asked if he can please just drive me back to my car as clearly he doesn’t want to be on a date, and neither do I. But instead, I found myself sitting on a bench at a car wash while this guy bought 2 bottles of malt drink from the convenience store next door. He proceeded to crack one open, offering me the other. I declined and informed him that drinking at the car wash is surely not permitted. Sure enough, an employee came over and told him to throw it out. I once again asked to please be driven back to my car. But this guy insisted we get something to eat. At the time, I didn’t have a cell phone (it was that long ago) so I agreed to get something to eat if we could just go back to my car afterwards. He took me to some cheap sandwich shop then hid in the bathroom when it was time to pay. I sat there for 10 minutes before just paying the freaking check. Not surprisingly, he showed up immediately after I paid.
On the drive home he stopped once again, this time to get gas. He got out of the car to pump the gas and looked at the woman at the pump next to us, pointed into the car at me and exclaimed, ‘This girl can’t keep her hands off my junk!’ I was mortified. It felt like I was on a prank show.
Fortunately, he dropped me off at my car right after this. I ran out of that car as soon as he set it in park, and I didn’t look back. I could hear him screaming after me: ‘Where you going? I thought we were gonna bone!’
I need to add that I was very young and stupid when this took place. Never ever go inside a strange man’s house on a first date. Always meet at a public location. If you feel unsafe, leave. No matter how rude or awkward you feel leaving, it’s not worth risking your personal safety.”
Why Is He Here?
“I was at work, cashiering when a cute guy stepped into my line. I remember he had the most piercing, ice blue eyes I’d ever seen. He had sandy, light brown hair and olive skin and wore a tight-fitting shirt that accentuated his strong, muscular chest. We exchanged coy glances the entire time I was helping his group, then he left with his friends.
I continued working, when a few moments later he walks up to me and interrupts what I’m doing. He hands me a piece of paper with his number on it and tells me that I should get in touch. We exchange one long smile and then I’m back to work.
A few days later I text him, reminding him who I was. Before long we were chatting back and forth often.
The only problem was, he seemed to get offended by completely harmless things I would say. He would take, what I saw as a completely innocuous sentence and interpret it into an insult. It was so elaborate I’d have to take a moment to wrap my head around just how, he managed to so twist my words as to find anything bad in them. I liked him, I was flirting with this guy, there was no way I was trying to insult or criticize him at all.
He would come back at me with a super aggressive message and snap at me, so I’d calmly explain what I had really meant and that I was not insulting him at all. I assumed at first that perhaps I had been unclear with my phrasing. Then I assumed that once we got to know each other better he would no longer be so defensive. I was quickly running out of reasonable explanations for this behavior in my head however and even read some of his texts to my best friend, who was also puzzled by his behavior and appalled by his aggressive replies.
He could also get very combative for, almost no reason whatsoever. What could be a pleasant conversation would be framed like a challenge. To give an example, he asked me what I thought about smoking. I explained that I had asthma and didn’t want it around me but if someone chooses to smoke, that is their decision. He responded ‘Good. We have an understanding then.’
Up until that moment I had no idea he smoked and had no clue we were reaching any sort of understanding with one another. It could have been just as easy to say, ‘Hey, I smoke, is that okay with you?’
Eventually he asked me out to the movies and I agreed. We were going to meet at the theater, so I drove there and texted him when I arrived. I waited a bit for him to show up and then saw him riding up on a bicycle. I was surprised that he didn’t have a car but figured it wasn’t that big of a deal. He was only 18 and going into the military soon, so I figured a car was an investment for some other time.
I’m glad he recognized me and waved because I did not recognize him at all. He had shaved his head and looked like a completely different person. I remember searching for his ice blue eyes because gone was the super cute boy I met a few weeks ago. I never realized that something as simple as shaving your head can completely change the way that someone looks.
His drastic change in appearance may have had a stronger effect had I not been surprised by something more pressing. Another person rode up on a bike behind him and the two greeted one another. They both acted as though it was a coincidence that they had run into each other and I figured it was no big deal, they would say hello and be on their way. His friend appeared younger but it could have simply been a height difference. He was short and a little husky, with blonde hair. He wore a black T-shirt and shorts and acted much less mature than I would expect of someone our age. He did not make much of any attempt to greet me upon his arrival and simply talked to my date as though I were not present until we were introduced. Together, the three of us walked inside.
I had refrained from eating much earlier in the day, in the hopes of getting some popcorn. I was disappointed as we walked inside and my date immediately steered me away from the food area as soon as we approached it. I would have been willing to pay for my own popcorn of course but it was never asked of me if I was hungry or wanted any food. I tried to ignore my rumbling stomach to focus on the much more alarming conversation at hand.
His friend asked what movie we were seeing and then said he would switch to come see the same thing as us. I, perhaps naively at this point, assumed that he would of course, respect our space and would sit elsewhere during the film. The two of them were having a grand time talking while I awkwardly followed along, feeling like a third wheel on my own date. They also had many inside jokes and references, so the conversation they were having wasn’t much of anything I could follow along with or interject in. I walked silently after them, biding the moments until we sat down and his friend was finally out of the picture.
We select our seats when I hear my date say ‘what are you doing?’ I looked over to see his friend running up to the seat next to me ‘I’m going to sit with you!’ he said and then plops down. My date made some half-joking comment, I think intended to make the friend leave but the friend had decided he was going to stay and my date didn’t push the issue, or even ask him directly to give us some space.
I was immensely annoyed with this presumptuous friend who had settled into the seat next to me. Was this some sort of pathetic attempt to ‘steal’ his friend’s date? Was he just playing a prank and messing with us before he was going to leave? Was this entire thing planned by the two of them who were merely pretending he wasn’t invited along the whole time? Or was he actually that ridiculously clueless that he didn’t realize people might want some alone time to get to know each other on a first date? I was mulling this over in my head, silently fuming.
But a moment after seating myself my date turns to me and hits me with this question,
‘If a transgender woman is interested in women, does that make her gay or straight?’
Apparently the two had been debating this for some time and the question invoked quite a bit of raucous laughter from his friend. I was less amused and told him I didn’t know.
The duration of the date consisted of me sitting between the two of them watching the film awkwardly and wondering why on earth his friend was tagging along. I took turns sneaking glances at my date, completely in disbelief that a simple haircut had transformed him from the chiseled Adonis I had met at work, into someone unrecognizable and not at all very attractive and staring at his friend intensely, seeing if he would look at me just once or feel me silently fuming next to him.
A part of me briefly wondered if the wrong guy had waved at me and my real date was out in the hall looking for me, yearning to sweep me off my feet and take me out of this accident I had stumbled into. But they were the same piercing blue eyes that had caught my breath. But gone was the smooth, charming, forward guy I had met.
Usually on movie dates, especially first dates, it is followed up with dinner or at least some alone time to sit and chat, so as to get to know one another. But as soon as the movie ended, he and his friend were back to joking around with each other and I simply forced a smile long enough to stand up and follow them out of the theater.
We stood outside in the parking lot, his friend still standing right there the entire time. He gave me a hug as his friend quipped ‘awwww’ sarcastically. There was no opportunity to talk or get to know one another. In fact I’m fairly certain the two of them talked to each other more than they talked with me. His friend had not made any effort to talk to me or include me in conversation and in fact steadily avoided even acknowledging my presence the entire time. He would always position himself to be facing away from me or looking elsewhere. Although he sat beside me he would simply lean over me to talk to my date while we were in the theater and when he did talk, he only looked at and addressed my date, and often brought up something only the two of them could understand.
I walked back to my car and watched the two of them pedal away together, shaking my head.
After getting home I had long since decided I was not interested in pursuing this any further. But to be polite, I texted him to thank him for the date and tell him I had a nice time.
He said he had a good time as well.
It was then that he pulled the same stunt he had multiple times before. I said something completely benign, simply exchanging pleasantries, and he interpreted it as some sort of insult and began snapping at me again. By this time my patience for him had worn thin and instead of calmly placating him as I had before, I got an attitude right back whilst explaining what I really meant. We agreed to let it go and wished each other a nice night.
I knew for sure that I was not texting him ever again but it wasn’t an issue because he never tried. I guess the one moment I gave him a little attitude it left him with a bad taste in his mouth.
This was a person who had no problem snapping and barking at me over text message over the most innocent of texts but who didn’t have the ability to tell his friend to give us some space while we were on our date. You can only act so tough when you ride around town on a bicycle and let your immature best friend crash your date.
Well, it’s been a few years and I still have a bad taste from him and that pathetic bromance cough I mean date he treated me to.”
What A Creep
“This date was great… until it wasn’t.
I went to this local restaurant by myself once a week. It was the perfect place to be alone. I’d have a small meal, drink some tea, and read a book.
After a month of this routine, the chef comes to my table and asks how I liked my meal. He was 8 years older than me, tall, dark hair, dark eyes, mysterious, and extremely charismatic. He had his master’s degree in neuroscience. He was working part-time at the restaurant until he decided where to go for his doctorate. We talk for a bit, and he asks me if he can give me some more good food… at another restaurant this weekend. He was one of the most charming men I’d ever met from such a brief encounter.
We go on our first date, and everything went really well. I could not believe he had been single for long. Despite everything being perfect, there was something unsettling about him. Something I could not quite put my finger on.
I view intimacy differently than most people. I have to completely trust someone before we can be intimate in this manner. I view love making as giving a partner domination over my body. That’s just who I’ve always been. I take it seriously.
He asks if he can stay over at my place when he walks me to my door. I politely tell him he can watch a movie with me, but I’m not ready for him to sleep over. He pretends to fall asleep on my bed in the middle of the movie. I sense he is not actually asleep. When it’s over, I gently wake him up and tell him I’ll see him soon.
Here’s where things go sour.
The next weekend we have our second date. I get into his car, and I can sense something is different. He didn’t seem like the same person I met last week. He makes a few rude and snide comments about my outfit, and then he laughs. I do my best to ignore them and try to see the humor.
Then he starts talking about how pathetic and stupid he believes his mother is. She had called him earlier because she had a small tree that was dying, and wanted his advice. She had been praying and caring for this tree, but it wasn’t getting better.
‘She’s so pathetic and stupid. Kids are dying all over the world from hunger. You think God would care about her stupid little tree?’ He then starts laughing this creepy laugh as if he had told a funny joke. It sent shivers down my spine. What on earth?
We get to dinner, and his steak was not cooked to his liking. Instead of being polite to our waitress about it, he complains and talks to her so rudely, that she takes it back to the kitchen trying to hold back tears. He then starts loudly talking about how she must not be that bright. The tables around us keep looking our way.
I was disgusted and mortified.
He’s driving me home after dinner, and abruptly stops the car along this side street. I do my best to remain calm, and not let fear keep me from preparing for what is about to happen.
He aggressively turns to me and gets really close to my face. ‘I’m not letting you lead me on. I’m a catch. Either you are mine or we’re nothing.’
I’m in an awkward position. We’re a few miles outside of town with no one nearby. He was unpredictable. I had no idea how he was going to react.
I don’t move away as he gets in my face. I didn’t want him to sense I was scared. ‘Alright then. We’re nothing.’
He starts shouting and calling me horrible, vulgar names. I tell him I’m walking, and get out of the car. He laughs and yells his only regret is wasting his money on my dinner.
He drives off, I’m alone in the dark, wearing shoes and an outfit not suitable for walking after dark in the cold, fall weather. After walking for a half hour, I finally get cell service and call my roommate.
He texts me a few days later and apologizes for how he acted, and wants to take me to dinner again. I politely decline. He spends the next few weeks bashing my name around town and on social media. I just ignore him and, eventually, he stops texting me and leaves me alone.”
“I’d agreed to meet this guy at a local restaurant for our first date. We’d been speaking extensively for a few weeks, talking on the phone, video chatting, texting – there was hardly a social media that we did not use to talk. I was excited to meet him in person for the first time.
I arrived at the restaurant about 10 minutes early, wearing jeans and a sweater. The waiter informed me my date hadn’t arrived yet, but I was content to wait, ordering a glass of water.
Another 15 minutes rolls by, and I find myself bouncing my knee impatiently.
Relax, Aarden. Not everyone is so obsessive about punctuality as you.
Tick, tock. It is now 30 minutes after were supposed to meet.
I guess he’s not coming.
I decide that even if he isn’t coming, I may as well grab a bite to eat. I order a hamburger and fries, and leave the booth to go to the washroom.
Upon returning to the booth, a tall, bearded gentleman sits in my seat. I recognize him from his profile immediately.
‘Sorry I’m late, dollface. Got caught up at work.’ He apologizes, motioning for me to sit.
I cringe internally at the nickname, but smile and greet him, sliding into the booth. The waiter sets my food down in front of me, while handing him a menu.
He frowns at my plate. ‘You ordered without me?’ he inquires, staring at my burger like it has personally insulted him.
‘Oh… Yeah. I hadn’t eaten yet today, and I was starving.’ I suddenly feel embarrassed, like I’ve done something terrible.
‘Bad choice. If we date you’re not going to eat trash like this.’ He states, never raising his eyes from his menu.
I laugh halfheartedly. Is he kidding? Is he nervous?
He orders two drinks from the bar. Oh, maybe he is just nervous.
‘Oh, no. I need to drive home.’ I tell him, stopping the waiter.
‘They’re not for YOU.’ He hisses, tossing the menu at our waiter.
The conversation does not flow at all. He glares petulantly at his phone. His drinks arrive. He drinks them both immediately, and orders two more. He orders food. Some kind of vegetarian dish.
Suddenly he raises his head, and smiles. ‘I’m sorry, where are my manners? How was your day?’
Dumbfounded, I tell him about my day. Labs. Classes. The usual. I ask about his.
‘Oh, you know. I smoked a bit. Walked my dog. Slept. Smoked more. Actually,’ he says, removing a rolled joint from his pocket, ‘wanna go smoke outside?’
Now, don’t get me wrong. I’ve been known to enjoy some Mary-Jane in my time, but never in a public place – and never with some random man I just met.
‘No, thanks.’ I say. He frowns. ‘Are you high right now? And didn’t you say you went to work?’
‘Oh, work. Na. And yeah girl, I’m high as a freaking kite. Didn’t know you were so uptight.’
Well, okayyyyy then.
His two drinks and food arrive. He orders a bottle of bubbly. At this point, the drinks and smoke are clearly affecting him, as he speaks loudly. People stare. I attempt to nod politely, but I am feeling the weight of the restaurant’s gaze. His words slur.
A waitress walks by, and he stops her.
Probably asking for more drinks, I think.
Oh, no. He doesn’t ask for more liquid courage. He asks for her phone number.
Oh, no. If my eyebrows had raised any further up my head, they’d have become a permanent part of my ponytail.
She laughs uncomfortably, and attempts to leave. He grabs her wrist, and she quickly walks away. The entire restaurant heard the exchange. I resist the urge to run screaming towards the nearest fire exit.
Same, buddy. Same.
The check arrives. I move to pay for my small meal, amounting to two glasses of water and some pub food.
‘Whoah, whoah.’ He holds out his hand. ‘Wanna go back to my place? Watch a movie? I’ll pay for dinner.’
Oh, buddy. I was not born yesterday. There will be no ‘movie watching.’
‘No, but… uh, maybe next time.’
‘Fine, wasted my time then. Let’s split the bill.’ He shrugs, and I surmise that I’ve never met a more rude human being.
‘Okay, I’ll pay for my food.’ I move to grab the debit machine from the waiter, who has remained awkwardly perched near our table.
‘Did I stutter? Let’s split the bill.’ He glares at me, shoving his receipt towards the waiter.
I’m an undergrad student. I have -121$ disposable income. There’s no way I’m paying for the brewery of drinks he consumed, nor his fancy entree.
‘Nope. Not happening.’ I glare openly at him. ‘Pay for your own stuff.’ I slap a twenty dollar bill on the table, which is more than enough to pay for my meal, but hardly cuts into his.
‘Hey!’ I slide from the booth. He screamed obscenities at me, but the waiter keeps him to his seat. Thank God.
I practically run to my car, turning the key in the ignition.
Holy god, I think. This is why I stick to women.”
“I was in a dry spell after breaking up with my boyfriend of four years. Every date I went on was sucky in its own way, and I was losing faith in guys pretty fast.
My step-mom asked if she could set me up on a date with her cousin’s roommate—she described him a little bit better than I’d give him credit for. She said he was nice, attractive, had graduated, had a job, and an active social life. Oh, and he was six-four, which, admittedly, was a bit of a lure for me.
I showed up at the coffee spot we’d agreed on and… very clearly, the picture he’d sent me was very very very old. As in, maybe taken when he was 18? 19? And at the time of our date, he was around 26 or 27. Whatever, I decided, he was nice-enough looking,
The date started out fairly normally. He ordered a complicated coffee drink, I got water, and then he ordered honey-toast (if you’ve never had that, I highly recommend) for himself.
I’d said maybe four words, ‘Hi, how are you?’ before he started in.
‘You’re really pretty,’ he said flatly. There was something in his face that told me he was annoyed. ‘Like, really pretty. Prettier than the pictures Lisa sent me.’
I shrugged. ‘Thanks, I—’
‘Seriously, you’re way prettier in person,’ he cut me off. He looked around the café nervously, his leg bouncing beneath the table. ‘Lisa didn’t say you’d be so pretty.’ He plucked nervously at his shirt.
His words were nice…but there was something aggressive about the way he said it.
‘Okay.’ I didn’t thank him again, since it didn’t sound like a compliment anymore. ‘Uhhhh, Lisa mentioned you’re a chef?’
‘Yeah, well, I will be. I’m still a grunt in the kitchen.’
‘Is that what you went to school for?’
‘No, actually, I went to circus college.’
I paused, the straw in my water still resting on my lip. ‘I’m sorry, what?’
‘Yeah, you know…clown school. Where you learn to be a clown.’
I just blinked at him. ‘But you’re a chef?’
‘Yeah, I mean, cooking is my day job. Being a clown is my passion—but there’s not a ton of clowning jobs out there right now.’
I didn’t reply. I was positive he was messing with me—this had to be some weird joke, right?
Before I could ask, his phone started ringing. He pulled it out of his pocket and answered. ANSWERED HIS PHONE while sitting RIGHT THERE, on a DATE.
My jaw dropped.
What. On. Earth.
‘No, no, it’s fine,’ he said into the phone, turning slightly away. ‘Yeah…yeah, 7:45? I think I can make that. Yeah—I’ll meet you out front. Okay. Bye.’ He set his phone on the table and turned back to me. ‘So, you think this’ll be wrapped up by 7:45?’
‘Um.’ I checked my watch. It was already a little past seven. ‘Yeah, for sure.’
I wanted to leave right then, but part of me still wondered…
‘So, clown college?’
He launched into a whole spiel—going on and on about learning to face paint, his clown name, wearing big shoes and fitting in small cars. After the clown conversation, he switched over to talking about his apartment and his pets and his favorite hobbies—karaoke and his clown posse bowling league—and a slew of other things, not letting me get even a single word in edgewise. I sat in almost total silence for close to 30 minutes.
He finally stopped talking when the café worker came back over to drop the check.
‘So,’ he said once the café worker was gone, ‘Wanna go 50/50?’
‘Yeah, no,’ I said, shaking my head.
‘That’s kind of messed up.’ He rolled his eyes. ‘Girls always expect guys to pay for them. Especially pretty girls like you. I’ve been really cool this whole time, but I can’t deal with this. You think just because you’re sitting there batting your big blue eyes, I’ll pay for whatever you want?’
‘Dude.’ I sighed. ‘First of all, you’ve talked about yourself for an hour straight. Do you know anything about me? Anything at all? You ordered a $13 drink and a $15 dessert. I got…water. In what universe would I split this with you?’
He sighed. ‘Is this about the clown thing? I should’ve known you wouldn’t understand.’
‘Nope.’ I stood up so fast my chair screeched behind me. ‘You’re right. I don’t.’
Well, I Ruined That
“I used to be a bartender. Which mainly involved 8 years of being tired, having a sore lower back and screaming ‘FF OFF’ in my head when people came to the bar.
Still, I was under the impression there were certain trade-offs to living a night owl life. First and foremost of which was – attention from girls.
Oooh boy, let me tell you now…that didn’t come true. In fact when women did interact with me directly it was usually to be rude.
I remember kicking a girl out once for being too inebriated and dancing on tables inside, and she said ‘I’m sorry you’re gay’ on the way out.
I still don’t know how that made me gay. Does it really make you gay to ask a woman to stop dancing on a table? If proper table manners and a clean space to eat a Caesar Salad is a sign of homosexuality then sign me up.
But among all the mayhem and madness there was actually one time when a girl showed some clear interest.
She was blonde and short; wearing black fishnet stockings with a black corset top. Super cute but strange choice of outfit (outside of a dungeon). She’d been in my bar for a while, drinking on this particular Saturday night with her mate, just the two of them, and while they were getting loose, thankfully they did not try and dance on any tables.
By the time it got close to midnight, the bar now drowned out by the sounds of the extremely average DJ we would hire, it was hard enough to hear anyone order a drink let alone have an actual conversation.
So when this little blonde cutie came up to the bar and started trying to talk to me, I had no idea what she wanted. So, in all her crafty feminine ways, she whipped out her eyeliner and wrote her phone number on my arm in big, black, bold numbers.
I tell you right now, I’ve never felt more like a big man.
Who’s gay now you inebriated table dancing stranger!
A few hours passed, and she left later that night, though you couldn’t wipe the smile off my face. So as the night became early morning and the bar closed up, I whipped out my phone and texted this mystery girl.
Thinking she’d be tucked up in bed, she actually replied right away saying she was still in the city and keen to catch up for a drink. So I zapped her some trademark charm via text – relying on my years as a powerful storyteller to hit her with a magic line like…‘U r pretty hot. Let’s go on a date right now’.
And they say romance is dead. Just 20 minutes later this random little cutie was walking with me in the still, cold air of a quiet Sydney City.
Of course, I hadn’t totally thought this late night date through. I worked in a late night bar on Sydney Harbor. By the time we’d closed it was almost 3am.
So not only did I need to find a venue that would still be open. But it ALSO had to be so relaxed with their drinking laws that they would let in a super hammered girl wearing fishnet stockings.
So I made a judgement call that very quickly became the worst date I’ve been on. I decided we would go to…
A gentlemen’s club.
The second we arrived I knew I’d made a grave error in judgement. I figured we’d stand up the back and have some quiet drinks, treat it like a bar. That was not the case.
The moment we walked in a hostess ushered us to a small collection of couches and tables by a long stage. Without blinking I’d been convinced to buy 2 x drinks for an outrageous fee. All the while my very cute date in fishnet stockings sat quite glumly next to me.
Turns out she had never been to a gentlemen’s club and was only in her early twenties. I asked her if she had ever wanted to see what one was like, thinking it might unlock some desire deep within her fishnet wrapped soul, and that maybe she might enjoy the experience.
She said ‘no’ quietly as a group of loud businessmen bustled past.
I don’t know if the highlight of this bad date was realising I didn’t even know my date’s name or when the hostess told her she was pretty and asked if she’d ever thought about working in there.
I’ll admit, in hindsight it went downhill pretty quickly from the start. My date didn’t finish even her drink. In fact, we barely had a conversation for the 30 minutes or, so we were there. Eventually, inevitably, she left – falling into a taxi to go back to wherever it was she lived.
So I sat and finished off both our drinks instead.
I think I realised at the time it was the worst date I’ve ever been on, and it was entirely my fault. I have no doubt that girl tells the same story to this day.
And as a dancer stepped onto the table in front of me to dance, I also realised it might actually make me gay to ask her to get off after all.
So I let her keep dancing on the table.”
No Wonder He’s Been Looking So Long
“Hoooo, boy. This one was a doozy. Back in about 2006, I met a local guy online. We chatted back and forth a few times, and then decided we would go to dinner at a public place. I explained that I had no night vision and did not care for dark places, and that I was allergic to smoke. That was fine, he said. We would go to a nice restaurant, he said. The weather took a turn for the worse by the time our date rolled around, and we’d had a snowstorm. He pulls up, honks the horn, and I go out to his car. I’m dressed nicely for a ‘nice restaurant.’ He’s in worn khakis and a plaid shirt.
We’re driving to the restaurant with some minor small talk, him boasting about how well off he is and telling me he’s a retired Methodist minister. Then he asks me how long I’ve been online. ‘You mean on an online dating site? About a month.’ He replied that he’d been on eHarmony for two years and couldn’t find anyone. Alarm bells that had been ringing softly became louder. We get to the restaurant, which turned out to be the bar in a hotel, dark and full of smoke. We order some food, and the entire time, his head is swiveling as he’s looking around the room, presumably for someone better. After a few minutes, he tells me that he hates when people put up out of date pictures and lie on the dating sites. I asked if mine was accurate, and he agreed it was.
He then starts telling me about one woman he took to dinner, but she was older and much fatter than her picture. He decided that he’d just make fun of her, and that he was confident that he’d get laid, because you know, she ‘must be desperate.’ The alarms are now ringing loudly, and I know I need to escape. By this time, he’s finished his burger and is ready to go, about a half hour total. We get in the car and drive toward my home. In an effort at small talk, I ask if he sees his kids often. No, he does not. We pull up to a stoplight, and a black SUV with a man and woman pull up next to us in the left turn lane. He looks over and says, ‘That prick can’t even drive that car properly. And I bet he can’t ride that woman right either.’ Silence until we get to another light 2 miles from my house.
He asks me, ‘So what did you say you do for a living?’ I told him that I’m a graphic artist and that I make jewelry. To my horror, he says, ‘Sooo, does the word Jewwwww come from the word jewwwwwelry?’ (It was on my profile.) I can’t believe it. So I say, ‘I also make quilts, you wanna make something out of that, too?’ Silence until he pulls up in front of my house, such that I have to cross the icy street to get to the sidewalk. I’m not even done closing the door and he takes off, leaving me in the middle of the street.
Thankfully, I got in the house without incident, other than to my psyche. And that is the absolute, most pathetic date I have ever been on.”
“About 5 months after I was in a long term abusive relationship (LONG STORY) I decided I would enter the dating pool again. I believe I was on the dating app Bumble. I met a few nice guys here and there, but nobody I really jived with until I met a guy, we’ll call him Dan. Dan was very attentive and charming via text in the days leading up to our first date. On the first date, he invited me for a drink at a cool lounge in NE Portland. Before I arrived he was joking about how he would be difficult to find due to lumberjack beard and a black corduroy jacket on (typical Portland look). I found him anyway, and we sat down with our drinks (he paid) and began chatting away. He was very nice, attentive, charming, just like his texts. He was very good-looking and we had a lot in common and I felt like I finally was getting along with someone new and that this could have some potential. About 30 minutes into the date he started talking about a second date and how he had season tickets to the Portland Orchestra and that he thought that given both our musical backgrounds it would be cool to attend a show sometime. I agreed. After a second round of drinks (seemed like we both didn’t want the date to end) he walked me to my car and gave me a sweet kiss on the cheek and sent me off.
We kept texting the following days and decided to meet again for happy hour before we went on a third date to see an orchestral show the following weekend. I arrived a little early at the restaurant of choice and waited no longer than 5 min for him to get there. No worries. Except when he arrived, it’s like a switch had flipped and he was completely off. I would ask him a question to get to know him more or follow up on a conversation we previously had via text and he would kinda just stare at me or take a very long time to respond. He seemed disinterested. I wrote it off as maybe he was tired or had a bad day. And then out of nowhere he started asking me questions back:
Dan: When was your last relationship?
Me: About 5 months ago, I kinda took some time away from dating
Dan: Why? Did it end badly?
Me: Yes (without going into detail), Let’s just say he wasn’t a very nice guy.
Dan: Did he not suck on your knockers enough? He’s grinning as he asked this.
Me: awkwardly and very taken aback Huh?
Dan: I asked if he didn’t suck on your knockers enough.
Me: I know what you asked but that’s just a very awkward and weird thing to ask, also it’s not really any of your business. I squinted my eyes at him and cocked my head to the side to figure out where this was coming from.
Dan: I’m sorry, that was rude, I just haven’t gotten enough sleep. He smiled at me.
Me: Umm, that’s okay.
Dan: Anyway, what do you say we get out of here and get some fresh air.
Me: hoping that was a fluke Sure, that would be nice.
We were in Downtown Portland walking around store to store and we just chatted and window shopped. Things still felt off and I was getting ready to just end the date and walk back to my car when he spotted a Valentine’s pop-up shop. Valentine’s Day was about a week away and there was this little boutique that was selling all kinds of kitschy gifts and trinkets. He asked if we could go in to check it out as they were also advertising free bubbly and chocolate samples. I agreed, what could go wrong?
It ends up that the boutique had several vendors who had set up their little tables with their artisanal crafts and Valentine’s gifts for sale. We walked around, drank a little bubbly and pretended to admire the stuff on sale. At some point he darted towards a table that was selling something called ‘Clone-A-Willy’, he called over to me and beckoned me to come join him. I walked over and he told the lady that was selling her product to explain what it was to me. Basically, it was a putty mold that a man would encase his Johnson with and then when it dried you would send it back to the company, and they would fabricate a silicone toy that was the exact mold of your partner’s junk. This isn’t that strange of a thing because Portland is known for its weirdness and this seemed kinda like a gag gift for Valentine’s day. Dan was super excited about it as he asked several questions and kept looking at me for my reaction. It was almost like he wanted me to feel uncomfortable about it and was trying to elicit a reaction from me.
I asked if we could leave as I made up an excuse about why I needed to be home. He walked me to my car again, grabbed the back of my neck as he went in for a kiss. I didn’t kiss him back, it felt very strange and forced. I pulled away but the way he had his hand on the back of my neck kept my face close to his. He then whispered in a very commanding tone:
Dan: I want you to go back in there and get that clone-a-willy kit. I’m gonna take it home make the mold, send it back to the company and then bring you the finished toy. Then I want to see you pleasure yourself with it in front of me.
Yep, that’s what he said. I was kinda terrified; do I really attract that many creepily weird men? I was frozen for a second, he was grinning at me with his all American jaw jutting out. I did the only thing I felt would get me out of there, so I sort of shrugged and laughed it off as I very slyly replied with ‘But Dan, my rule is I have to go on a third date before I use a silicone mold of the guy I’m seeing.’ That did the trick, he bust up laughing and then responded with ‘Then let’s pick it up after we see the show this weekend.’ I nodded my head and the moment he released my hair from his grip I climbed into my car, smiled at him from the driver’s window and drove off.
He texted me the next day to let me know the schedule of the Symphony he wanted to go see with me that weekend, I just said that I was not interested and that he made me feel very uncomfortable and that I really did not want to see him again.
The weird thing was that he actually agreed that he was behaving badly, but after my previous boyfriend, I really was not about to give this guy another chance.”