Chicagoans Share Their Worst Online Dating Stories

awkward date
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Spending too much time on Tinder, Bumble, or OkCupid will make any sane person yearn for simpler times. You know, like when singles met potential mates at corn husking bees or whatever. Dating apps have given us unprecedented access to every nut job, borderline sociopath, and bunny boiler in Chicago, and having a nightmarish experience has become some sort of twisted rite of passage. But just how bad does online dating get? We asked a handful of Chicagoans to share their worst online dating stories, and we were not disappointed.

It’s time to burn your copy of The Game, dude

“I’d matched with this guy on Tinder and we quickly discovered that we had a bunch of acquaintances in common, including some high school classmates and old coworkers. After chatting for a couple of weeks, we decided to meet up at a bar. Everything was going really well, until he got a few drinks in him and he began telling me obviously fake or exaggerated stories about how wealthy and successful he is, which was a huge turnoff. I could tell he was annoyed that I wasn’t falling all over him after hearing his bragging.

"Visibly frustrated, he decided to inform me that his ex-girlfriend knew me, and that when she found out we were going on a date, she’d called me a whore. It seemed he was desperate for me to A) ask who this mystery girl was; B) say nasty things about her in return. I got the sense that he was trying to instigate some sort of catfight to feed his ego, and I wasn’t going to play into it, so I changed the subject.

"Because it was still fairly early, we decided to visit his neighborhood bar. As we were walking in, he turned to me and said that he’d asked one of my former classmates about me before our date, adding, ‘Well, let’s just say that I was expecting a total heifer to show up for this date. I’m glad he was wrong about you!’

"At this point, it was pretty clear that he was attempting to play some type of ridiculous mind game with me. I wanted to run back out the door, but he quickly grabbed my arm and steered me towards a group of guys. After quick introductions, he left me standing there with his douchey friends while he made a beeline over to a group of girls and asked them if they wanted a drink -- and no, he never asked me if I’d like one.

"He sat there taking shot after shot, while I patiently waited at the other end of the bar like a jackass. After 15 minutes of being ignored, I decided to leave. I stopped to bum a cigarette on my way out and overheard a group of older men who were smoking nearby talking about my date. One said, ‘That scumbag Chris somehow managed to get a pretty girl like that, and then leaves her standing there. What a fucking loser!’ I was completely mortified.

"As I turned to walk away, he stumbled out of the bar after me -- quite obviously sloppy to the point of nearly blacking out. He followed me to my car and got in, and despite my better judgement, I decided to just give him a ride home rather than stand there and make a scene. Although it was less than a mile to his apartment, I had to pull over twice to let him puke. When he attempted to get out of my car, he fell over into the snow. While the idea of leaving him for dead in the snow was slightly tempting at that point, I helped him inside and got him to his room. As I turned to leave, he curled up in a ball and started crying, saying, ‘Please don’t leave me... I love you. I just wanted us to be a happy little family with a baby. That’s all I want. I want us to get married and be a happy little family together…’

"As I closed his door, he yelled after me in a strangled sob, ‘WHY WON’T YOU BE MY GIRLFRIEND?!?!?!?!’”

-- Elizabeth M., Portage Park, 33

Is it a deal breaker if I only speak American?

"A few years ago, I went on a date with a lady I met via OkCupid. We wound up going back to my place to watch a movie, which was really just background noise to our conversation. I had recently returned from a trip to London and I was telling her about it and about my plans to move there, to which she responded: ‘Do you speak any other languages?’ I figured maybe she was just a subject-jumper. You know the type -- jumps around from topic to topic with little to no segue. So I answered her question, then followed it up with ‘Why do you ask?’ BAD IDEA.

"She says: ‘Well, how are you going to get on in London?’

"I asked her what she meant, and she responded, ‘How are you going to get by in London if you don’t speak the language?’

"My internal monologue: ‘Oh crap.’

"My verbal response: ‘Wait... what language do you think they speak in London?’

"Her answer (and I shit you not, this is verbatim): ‘I dunno. French or somethin’?’

"My internal monologue: ‘CRAP! CRAP! CRAP! ABORT! ABORT!’

"Unfortunately, there’s not a gentle way to say ‘Ok, this date needs to end because you’re far too dumb to allow this to go on any further.’ After a painful amount of time, I finally managed to convince her that the date needed to end, claiming that I was tired and had work the next day.”

-- Bill M., 31, West Ridge

"'Oh, those bruises are from the IVs! I got pissed off at work so I took a bunch of OxyContin and drank a fifth of vodka and passed out at my desk. I’ve been in the psych ward for the last week and just got out this morning, right around the time I messaged you,’ she answered, as if it was no big deal."

Let’s hope your wife isn’t reading this, buddy

“My best friend is a wedding photographer and after shooting several weddings where the couple met on Tinder, she was inspired to sign up for an account. She matched with a guy and -- noticing that we were mutual Facebook friends -- took a screenshot of his profile and texted it to me in order to get more info on him. Shockingly, her ‘match’ happened to be an acquaintance of mine who is VERY married. In fact, he posts all the time on social media about his ’amazing’ wife!

"I forwarded him the screenshots and asked him, ’What’s up with you having a Tinder account?’ and reminded him how interwoven the city is. He FLIPPED. He started telling me that he ’never had a Tinder account in his life’ and insisted that he must have been hacked. He claimed he was going to ’call Tinder’ and ’make sure someone pays for this.’ He even texted me a few days later to tell me that he had ’talked to Tinder’ and that ’he was part of 270 people who were hacked.’ I mean, he really sold the story!

"That was about a year ago, and I talk to the guy about once a month because we are planning our high school reunion. To this day, he ends almost every conversation with ’thank you for not mentioning that to my wife.’"

-- Kate J., 37, Logan Square

Well, that’s one way to get out of work...

“Recently, I was talking with a girl who appeared to be a great match. She loved literature, and I’m a huge book nerd. After messaging back and forth for some time, she went silent and stopped responding. Then, out of the blue, she resurfaced and asked me if I’d like to meet up that day. We met, and our conversation was going well, although something seemed a bit 'off' about her. Then I started noticing a few oddities... like the fact that her arms and the backs of her hands were laced in bruises and obvious needle marks. I finally bit the bullet decided to ask her about them.

"’Oh, those bruises are from the IVs! I got pissed off at work so I took a bunch of OxyContin and drank a fifth of vodka and passed out at my desk. I’ve been in the psych ward for the last week and just got out this morning, right around the time I messaged you,’ she answered, as if it was no big deal.”

-- William M., 33, Elmhurst

"A few months later I was browsing Tinder when I happened to stumble upon a different profile for Mr. Tinder: same photos, same basic information... except this profile had been created by a woman to warn other females about him."

Coffee dates were invented for a reason

“When I first started using dating apps, I often made the mistake of agreeing to dinner on a first date, not realizing that escaping dinner is much more difficult than escaping a quick coffee. Like with Question Guy. On our date, Question Guy asked: ’Do you believe in God?’ ’What do you want to name your kids?’ ’How many surgeries have you had?’ -- all unprompted, and all before the appetizers had arrived.

"I don’t think I’ve ever ordered and eaten tapas so fast in my life, just in hopes to hurry and get the hell out of there. Question Guy was relentless throughout the meal. ’Aren’t those the same pants you wore in one of your profile pics?’ (they were). ’When was the last time you got your hair cut?’ (ummm... ) ’How are you still single?’ (because I keep agreeing to dates with weirdos like you.) When the date ended and we stood up to leave, he of course ended with the classic, disappointed question: ’Oh. How tall are you?’”

-- Landis W., 32, Bucktown

We haven’t done anything bad and yet we still don’t want to see you, dude

“Exactly two years ago, I made my first foray into the rabbit hole that is Tinder. One of my first matches was a 26 year old military guy, who I met for drinks after work. I’d barely had a chance to sit down before he hit me a rapid-fire inquisition about my job, my family, and my hobbies. After answering around a dozen lightening-fast questions, I needed a break, so I decided to turn the tables. I went for the most generic first date question: I asked him what he did for a living. Strangely, I was met with complete silence.

"Finally, he answered, ’I’m trying to think of a response that won’t scare you’.

"’Mafia? Mob? Hit man?!’ I wondered. After a bit more silence, I probed a bit further: ’Can you tell me in summary? Just a few words?’

"’I’M THINKING!!’ he screeched.

"There was another long silence, and then he began his first tirade of the night: ’I don’t want to tell you too much. I don’t know you! Why would I share personal information with someone I just met?!’

"’Um... because we’re on a first date and that’s what you do... share information about ourselves,’ I responded. ’But, you know, whatever, tell me what you want.’

"’Fine,’ he answered. ’Let’s just say that if you ever did anything bad, you wouldn’t want to see me... ’

"Ooookay. In an attempt to make things less awkward, I changed the subject, and thankfully, our conversation started to flow a bit better for a short while. All smiles, I said, ’It’s a good thing I told you to be open at the beginning; we’ve had fun!’ I was met by more silence, and then... outburst number two:

"’Who do you think I was for the last hour? Do you think I was faking it?! I’m genuine! How rude of you to think differently!!!’ He yelled.

"I was cowering, highly embarrassed because he was making such a scene in public. I whispered that he was making me uncomfortable, which only resulted in more ranting. Blessedly, the bill arrived and he demanded that I give him a card to pay half. I happily obliged, glad to just be getting the hell outta there. We signed our receipts in complete silence, and it was incredibly awkward. Then, out of nowhere he looked up (seriously, this was the best part of the whole night... ), looked me straight in the eyes and said, ’What’s your favorite animal?’

"Me: ’Uh... I don’t understand... ’


"When we parted ways, he gave me an awkward handshake. As I was running down the stairs to the train, he yelled after me, ’MILITARY POLICEMAN!!!’”

-- Ashley C., 33, North Center

Who doesn’t love a good revenge profile?

“I matched with this guy on Tinder and was immediately smitten. We hit it off rather well, and eventually ended up meeting. He was gorgeous, a total sweetheart, was very successful (he worked in real estate -- a nugget which will become important later).

"More importantly, we were actually having an amazing conversation! He was completely different than any other guy I’d met on Tinder -- in fact, it had been a long time since I’d actually made that type of connection with a guy. Before we knew it, it was closing time, but it was clear that neither of us were ready to part ways. He hesitated before suggesting we go back to his place and watch a movie. And with that, it was decided: I was going home with Mr. Tinder.

"However, we didn’t have sex; instead, we spent hours and hours spooning, giggling, talking, holding hands, and kissing. By the time morning rolled around, he was very insistent that he see me later that day -- unfortunately, I had other plans that I couldn’t break. He kept trying to pull me back into bed and by the time I left his place (which was a very impressive condo, I should add), it almost seemed as if he might be ’the one.’ Unfortunately, he ghosted me, and I never heard from him again. However, that’s not the weird part.

"A few months later I was browsing Tinder when I happened to stumble upon a different profile for Mr. Tinder: same photos, same basic information... except this profile had been created by a woman to warn other females about him. According to the profile, she and Mr. Tinder dated for a few months -- in fact, they had been dating when I went on my date with him. He charmed her in the exact same way that he had charmed me, going out of his way to push the relationship along quickly, getting very serious, very fast. She explained that there were red flags -- signs he may not be who he said he was, clues that perhaps he was cheating -- but she brushed them aside because he seemed like such a ’perfect’ guy. She remained blissfully ignorant... until he totally flipped on her.

"In the profile, she explained that out of the blue, he asked her if she thought his brother (who was much older) was attractive, to which she replied that he was a good looking man. This caused Mr. Tinder to explode into a bizarre jealous rage so unhinged, she fled the apartment. After a few days, she tried to reach out in hopes of reconciling, but he responded by dumping her. She arranged to stop by his apartment on a certain day and time in order to pick up her belongings. When she arrived at the day/time he had selected, he refused to answer her texts or calls. She could tell he was home and was just playing games, so she jumped over the gate and knocked on his door... and that’s when cops came. He called the cops and claimed she was a stalker. Unfortunately for him, she had saved the conversation in which he agreed to meet her in order to pick up her things and the police sided with her and escorted her inside to get her belongings -- much to his anger.

"Months later, I was on the hunt for a new apartment and happened to stumble upon one I liked. I was just about to call... until I realized that it was HIS listing. Out of curiosity, I looked at his agency’s website, and found ’his’ condo listed. In fact, it appeared that it had been on the market since before we met, meaning that odds are, the impressive, nicely-decorated condo he took me to was actually a client’s, not his. In short, ’Mr. Perfect’ was actually a smooth talker, a liar, a user, jealous, hot-headed and possibly a sociopath.”

-- Eloise P., 33, Rogers Park

"We got a cab and started heading over to her sister's place. At a random red light in the wrong neighborhood, she just opened the door and jumped out. No coat, wearing high heels, and it was maybe 10 degrees out and snow was everywhere."

Date... or babysitter?

“A girl I'd been out with twice called me while sloshed and out at a bar, so I decided to meet up with her and do some bar-hopping. Big mistake. Things were fine at first, until we got to one bar and she found out that the guy sitting next to us was there because he'd gotten fired from his job. She stole his drink, slammed it herself, then yelled, ’You got fired because you're such a pussy!’ and straight-up punched him in the face. This girl was maybe 110 pounds, and the guy was double that. Punched. Him. In. The. Face.

"That was the first time I'd ever seen anyone get punched in a bar, and I was stunned. Honestly, we were all stunned. He looked at me furiously, and did that angry yell-whisper thing and said, ’Is this your fucking girlfriend?!’ to which I replied, ’Oh wow, absolutely not -- and I'd like to take care of your bar tab and leave immediately, please’ which he graciously accepted in lieu of a fight or a police report. So I paid for his drinks and left to get a cab.

"In the cab, I asked where she lived, because I'd never been to her place. Her address was apparently, ’By the fucking... by the fucking... by the whatever,’ because she had just moved and was so sloshed she had forgotten her new address. Then, apparently she decided that she lived somewhere near my genitals, because she grabbed them and then climbed on top of me in the cab and started making out with me. I didn't really know what to do because the whole thing was so weird, and I thought telling her to stop would be even more difficult to deal with (I didn't want to be punch number two) so I just kind of let her do it, which felt... odd.

"Since she didn't know her address and she was in no shape to be out by herself anymore, we went to my place. Upon arriving, she saw my cat, decided it was the dog from Anchorman, and started yelling, ’Baxter!’ while chasing her around the house.

"I told her she could sleep on the couch, and she said no. So I said she could have the bed and I'd take the couch, and she said no to that, too. I told her that we definitely weren't going to be sleeping in the same bed and suggested that she call her sister to get her address, and she finally agreed. However, she couldn't work her phone, so I asked her sister's name and flipped through the directory to find it, and then called the sister to get her address.

"We got a cab and started heading over to her sister's place. At a random red light in the wrong neighborhood, she just opened the door and jumped out. No coat, wearing high heels, and it was maybe 10 degrees out and snow was everywhere. I jumped out and yelled, "We're 20 minutes from your place, get back in!" and ended up having to chase her down. I finally caught up to her and threw my coat around her while we hailed another cab because the first driver just took off. We got another cab and I finally (finally!) got her to her sister’s house.

"When I dropped her off she said, ’I've had a great time tonight!’ and kissed me, then went inside.”

-- Tony C. 27, Lakeview

Did I mention that I’m currently in Tahiti eating filet mignon, Brad?

“While I was warned multiple times by multiple people that Tinder wasn’t quite the ideal spot to find a prospective relationship, I happened to create a profile. After about a week on the site, a guy (for the sake of anonymity, we shall name him Brad) reached out to a mutual friend of mine to ’set him up’ with me after coming across me on Tinder (sorry bro, didn’t swipe right back for you). To be honest, conversation was pretty great initially. He had a good sense of humor through text messages, as we all do because we have ample time to think of something witty to reply with, and the next step was to see if it could progress in person.

"First date was nothing to rave about, but it was a good time. A few beers and an order of fried pickles over country music, that we both mutually hated, at Bub City seemed to seal the deal for a second date. However, after a few dates things started to get weird. It became pretty clear that Brad was a compulsive liar. The reasoning behind why Brad felt the need to lie to me, over and over again, remains unclear. Not to praise myself too much here, but I do think I’m a pretty laid back girl. I truthfully don’t get pissed off easily, or at all, and I do trust the person I’m dating; until they give me reason not to. I started to truthfully think that he was a compulsive liar and maybe he just couldn’t help it.

"For example, one night, Brad cancelled a date last minute and told me that his boss decided to take his employees out for dinner. My response? ’JACKPOT! Go enjoy!’. I of course wasn’t angry; this was a work event. However, throughout dinner he was sending me pictures of oysters that his boss supposedly ordered, and a chocolate lava cake that they decided to cap off the fabulous work dinner with. Both photos were quite obviously Google images. Not sure what part I was more pissed off about: the fact that he lied, or the fact that he must have thought I was unintelligent enough to not notice the differing backdrops and tablecloths in each photo. Don’t even get me started on the lighting of the pictures. I never confronted him about it, partially because it was too fucking funny that he took the time to scroll through Google images to find these pictures. Props to him for choosing the best looking lava cake, though.

"It’s not over yet: Brad stated he was going to join my friends and I for a little Sunday brunch action. One hour later, no show. Two hours later, still no show. No text. No call. Me, on the other hand? Downing mimosas faster than I thought humanly possible. One whole day and some odd amount of hours later, and I got a text.

"He was in Colorado. Resolving his warrant for his arrest. I don’t think anything else needs to be said here.”

-- Nicole N., 25, Lincoln Park

"Aggravated, I responded, ’And you would have done what? Fought him outside in the street?! It’s not worth going to jail over!’"

This date will literally force you to drink

“I met up with this woman at an outdoor patio in Lakeview. She was terrific, but ten minutes into the date, I noticed she kept using the word ’literally’ every other sentence... and often incorrectly. At that point, I decided the date wasn't going anywhere because as a writer, I couldn't possibly see myself being with someone who didn't have a fairly basic grasp of the English language. Since there was no chance for a second date, I decided I was going to take a drink every single time she used that word. We were on the date for about two hours and I wound up having six beers in that time. Not surprisingly, there was no second date.”

-- Mark M., 33, Lakeview

Note to self: save that line for the next time I piss someone off

“I met a girl on Tinder and for our second date, we agreed to meet at my local watering hole. There was a huge line out the door and as we stood there, it became pretty apparent that she was totally wasted. She started groping me in full view of everyone else and while that might be exciting for some, I wasn’t into it. I wanted to leave, but I didn't want to leave her there alone for some other sap, so I resolved to stick it out for a bit and make sure she got home, then never speak to her again. When we got into the bar, we ordered some food and sat at the bar watching a group of completely inebriated guys make pathetic attempts to hit on the female bartender. They even came over and interrupted my date, asking if they could have some fries. I gave them some just so they would leave us alone. Mind you, the entire time, these guys were under the watchful eye of the bouncer, who appeared to be a few minutes away from throwing them out.

"Unfortunately, my date decided at some point that she'd had enough. She stood up and yelled over to them, ’SHUT THE FUCK UP!!!!’. Needless to say, one of the guys decided to get in her face. Alarm bells go off: I didn’t want to get in trouble for any of this. I moved quickly and asked the bar owner (who knew me) to transfer our tab and drinks over to a table at the other side of the bar.

"I thought my date would be grateful that I resolved the situation non-violently, but instead, she proceeded to chastise me for not standing up for the bartender, claiming that’s why she decided to get in this guys face. Aggravated, I responded, ’And you would have done what? Fought him outside in the street?! It’s not worth going to jail over!’

"I realized at a certain point I was just ranting and she wasn't responding. After a moment of silence, she creepily asked me, ’Who do I remind you of in your past? Because this anger isn't about me.’ At that point, I realized that I wasn't dealing with a full deck, and so I paid the bill and proceeded to leave the bar and walk home. Needless to say, I never spoke to her again.”

-- Will E., 36, Logan Square

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Lisa Chatroop has never boiled anyone’s bunny. Say hi on Twitter: @LisaChatroop or read more bad date online dating stories on