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15 Horrible Yet Hilarious Online Dating Stories

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15 Horrible Yet Hilarious Online Dating Stories

If you have been fortunate enough to avoid online dating, consider yourself very lucky. It’s a train-wreck and its odds of success are astronomical yet millions flock to it, leave it, and return to it. Like Shampoo, people rinse and repeat, asking why they keep meeting the same type of person yet they don’t consider the common denominator. Profiles are dubious at best, either with a list of demands so long that the user might as well be in a cave in the desert and reading it off on grainy video, or they surmount to “Just Ask.”  Of course, there are all kinds of personalities, however, you may find yourself hard-pressed to find someone who matches their description.

There are all types of people to waste one’s time with. Bunkers: a potential match that emails and/or texts all the time, yet never wants to meet. Reason: they live in an underground bunker and are scared of the Up Worlders. Ghosts: a potential match that is communicating with you, getting along famously, and then, they just disappear. Up and vanished like a fart in the wind. As if they are a ghost. Charlatan: portrays an image online however when you meet them, you find you have been duped. The old ‘Bait and Switch’. Those are just a few of the personalities one can find in the dating world of Onlineville.

Women, in general, have the hardest time. One female user says on the first day she signed up for a popular free dating site, she received around one hundred messages and continued to average fifty to a hundred messages daily. Finally, she got fed up with all the messages, the angry returns for not answering their email, the ever famous ‘D’ pics, and philosophical postulations like “U hot, wut up, bae?” With an inbox full of stupidities, the messages worth seeing are easily lost in the fold of the fishing or asinine ones and it not only sours the female on the idea of online dating, but, the good guys as well who start to think maybe they’re not so great after all. In actuality, the only problem they may have is that their message is like a needle in a stack of needles.

However, despite all this frustration and angst, there are some hilarious moments one can find solace in, knowing it could be much worse, you could be these people…

15. Why You Manatease Me So Much?

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via wikipedia.org

One male user met a wonderful woman online. She told him all kinds of adventure stories, life experiences and that she was a marine biologist. After they slept together, she proceeded to tell him a story from when she was an intern in college. She had been on an ocean expedition and the group came across some manatees. So overtaken by the event, she jumps in the water, lands on the back of one of the magnificent Walruses of the Sea— that happens to also be dead. The deceased manatee explodes on impact covering the poor woman in manatee innards and gunk. They had to rescue her from the sea and clean her thoroughly, the event was traumatic due to her love of the docile creature. As the male is giving her his condolences, she begins to giggle and tells him she made the story up.

In fact, she told him she had made up every story she had told him. Why? Because she said it was fun to do. He’ll never know how far she would go however, he never spoke to her again after that night.

14. First Date, Third Wheel

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John was excited about his promising first date with a stunning local music D.J. He anticipated an entertaining evening filled with good conversation, interesting stories, and chemistry. The date would be dinner at a local favorite Italian restaurant, candles, mood lighting, romantic languages, and a table set for— three.

Unbeknownst to John, his bad girl club D.J. was also a “nice Jewish girl” who believed in traditional dating values. Including bringing her mother along on their first date dinner. Imperative that John meet her and get approval. It’s unclear if he went on the date or not, however, it’s likely that if he did, there were not too many more after. Mothers can be picky.

13. Hi, I’m Mike and I’m An Online Dater

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Mike was usually dubious about dating in general. However, like most of us, a time comes where the idea sounds better than the alternative. So, he meets Dotty online and they seem to hit it off. He agrees to meet her at a neighborhood cafe. However, what Mike couldn’t have anticipated is what was waiting for him. Besides Dotty, there were several of her friends there as well, at least Mike thought they were Dotty’s friend. He came to find out that Dotty was a recovering alcoholic and these were her friends from the AA meeting she attends regularly.

The meal was awkward to say the least and then Dotty suggested they go check out a local event. Mike agrees if only to try and get some time to talk to her without everyone listening. The event? It was an AA meeting. Now, Mike didn’t drink much and when he did, it was social at best, however, Dotty brought him there to inspire a sober lifestyle. While Mike agrees that if it’s good for her, then good for her, but, it was not for him. There was no second date and now he attends ODA meetings, Online Daters Anonymous.

12. But I Need Somebody Too!

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via cbsnews.com

Ronald had it all lined up. A walk through downtown, dinner in a trendy restaurant and afterwards, cocktails at his favorite bar. All the same, when he went to meet Jessica he noticed something that she had failed to mention, while beautiful and, so far, charming, she was also seven and a half months pregnant. Ronald’s very first words to her on their date were, “Pardon me, but, are you pregnant?”

Jessica told him that a gay friend of hers had inseminated her with his sperm via a turkey baster. Ronald had to use all his strength to prevent the reflective eye roll. When he inquired why, being so pregnant, would she agree to go on a date, not to mention, fail to say that she was in such a state on her profile. She answered that she knew being pregnant would put her at a disadvantage and she stated that while her baby had her, she needed someone too. Instant Family Kit; just add Ronald.

11. Poetic Justice

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Cynthia had to admit she was smitten. She met Aaron on a popular site that some of her friends had found success on. He was whimsical, charming, and he was a professional poet. Which, anyone familiar with the industry knows, he was most likely broke. Nevertheless, this was not known to Cynthia and the romantic notion of dating a man so brooding and deep sent shivers down her spine. Aaron had planned dinner and movie, a little unoriginal especially for a writer with their finger on romance’s pulse, however she assumed he was flustered or nervous and opted for the old standby.

The date happened, however, there was nothing poetic about it. Dinner was at the fabulous IKEA food bar and the entrée was the five dollar plate of Swedish Meatballs, he even splurged enough so they could each get their own platter as well. Then it was off to the movie, not the latest blockbuster, or even a tired Romantic Comedy either. No, instead it was a movie shown in the local park, for free. Yes, that’s pretty romantic for those who can get passed the fact that it’s free. But it wasn’t just any movie. It was Spongebob Squarepants, and the park was full of children. When Aaron brought out the small blanket and looked at her and asked, “Why didn’t you bring your own blanket?” Cynthia was speechless. Maybe, Aaron, it’s because she thought it wouldn’t be necessary at the cinema, being indoors and all. It’s possible that the poet was inspired after the date. Perhaps in the realm of heartbreak since Cynthia never returned his calls. Poetic justice at its finest.

10. Yeah, Well, You’re Ugly

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via nymag.com

Michelle was a single mother, she put her son first and foremost, all the same, this didn’t help on the lonely nights where more than a friendly embrace was needed. She swallowed her pride and signed up with one of the dating sites online. She met Matthew after the first week of sorting through countless emails. He was level-headed, career-minded, and he loved children. After exchanging emails the two decide to meet for a drink the following Friday. Upon meeting, Michelle picks up on a strange vibe. He seemed to be infantilizing her, speaking to her as a child almost. Matthew told her how great it was that she was a “mommy” and when Michelle attempted to explain that she was more than just a parent and share her philosophy on the task of balancing life and child, he stops her and says, “You’ll always be a mommy, that’s the gift you get for having your son.”

He continued to belittle her and for the most part, simply wasn’t listening to anything Michelle was saying. When she attempted to point this out and let Matthew know how much she didn’t appreciate it, that she worked very hard and earned her place in life. All in a friendly tone gently nudging Matthew to understand that she was a strong, independent woman who needed no coddling. He gave her a disgusted look and, while shaking his head, said that he was glad to find out how ugly she was on the inside so early in the relationship. Suffice it to say, Michelle found that her son was the only man she needed in her life after all.

9. I Don’t Know If You’ve Heard…

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Jennifer was optimistic. She had never dated an artist before and the idea that he would enlighten her or show her a new perspective was very appealing. After spending a meticulous amount of time getting ready, Jennifer headed out to meet her Van Gogh. Upon meeting Bryan, she noticed he had a bad habit, he never shut up. Not just that, he spent the better part of the “date” talking about his current art project that was an interpretation of an event his father experienced over forty years prior. Bryan even dropped the old Hipster line of “I don’t know if you’ve heard of ___ , but, I am really into it.” Unlike hipsters, however, Bryan named off mainstream subjects that just about anybody has heard of, like, Miles Davis and Wes Craven.

Finally, needing a breath one could imagine, Bryan stops talking long enough to ask Jennifer if she did anything creative, what was her outlet? She responded that she enjoyed documenting things, writing down events and describing them with verbal art; a writer. She did so in a succinctly prim manner, being somewhat turned off by the obviously ego-laden artist. Bryan snorted at her answer and replied, “That’s a little self-absorbed.” He then continued on his humbling story of his life and perceived accomplishments. I don’t know if you’ve heard of a second date, but, it’s way too mainstream for these two, and Jennifer never saw Bryan again.

8. Window Shopping

via loweredexpectations.com

Samantha was not enjoying herself. After meeting Alex online, she thought what harm could one date be? However, she instantly knew she was not attracted to him. They were too different and she could tell by the way Alex mansplained everything, they would clash before too long. Nonetheless, the two had planned to shop some unique international grocery stores in Alex’s neighborhood. Samantha discovered you could like someone even less than not at all. He went about pointing out everything and telling her what it was, “That’s a baby eggplant!” or “Over there, is Farmer’s Cheese.” This was nothing new to Samantha, after all, she was a food writer. Samantha distanced herself as Alex continued to suggest he knew everything, at least, more than Sam knew.

After the grocery store tour, the plan had been to head out for a couple of beers, however, a storm moved in and forced the two under a small bus shelter. No matter the signs that Samantha had placed out, such as No, Stop, and Not Gonna Happen, Alex was blind to these glaringly obvious signals. He leaned in for the kiss, and without enough room to stop him, Samantha was forced to allow it. However, once the rain stopped, she made her escape to the subway. Samantha was sure she had not met a more pertinacious, egotistical man in her entire life and the next day the message she got from Alex sealed the deal, “I thought after meeting you I would never have to use this [dating] site again.” Suffice it to say, it merited no response.

7. It Happened Last Night, So I’m Calling Today

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via marjinalizm.com

Not all online matches lead to dates. Some don’t even leave the draft board. Gerald was close, however, still far off from the goal. He had made plans to take a match out to a night of dinner, dancing, and libations, the quintessential first date. He had spent the week meticulously planning the event down to the very tiniest detail. Even the walk through the eclectic street fair from the eatery to the club was a detail planned by Gerald. He could hardly wait for Friday night to come.

All for not, Gerald’s date would have a situation that forced her to cancel their plans. She told him that her family pet, the cat, had been viciously attacked by a wild dog the night before, resulting in the end of the poor kitty’s life. While he didn’t want to be insensitive, three circumstances gave him a tongue-in-cheek attitude. First, she told him this by text message. Secondly, although it happened the night before, she texted him this cancellation an hour before their date, and finally. The third caveat, she was still dating an ex-boyfriend and to please not contact her again. Gerald was happy to oblige all the same, a little downtrodden. However, controlling himself was not the problem.

She continued to send Gerald emails, mixtapes, emotional rants, and other messages. Well, she did say for him not to contact her again.

6. You’ll Regret Not Changing For Me

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Rosa was in a slump. Odd for any woman, she had not gotten a message in some time. Granted, it was a welcomed reprieve since the normal messages amounted to propositions and pictures of things you shouldn’t see of another until you’ve at least spoken for a minute. No matter, one day she sees that a new message has arrived in her dating site inbox. Expecting the worst, she actually finds a polite message simply asking, “Hey, I think you are cute and was wondering if you wanted to chat sometime?” Rosa always did her research, so she checked the suitor’s profile to see if there was some commonality. Everything looked kosher, however, he had a kid and, for Rosa, children were not her cup of tea. Generally, she would delete the message and move on to the next, all the same, being in a dry spell, she chose to respond with a let-him-down-easy kind of message. She thanked the man for the nice words and while normally she would enjoy at least chatting, the fact that he was a single father, having a kid, was not something she was interested in. Rosa closed the letter wishing him luck and thought it the end.

The next day, Rosa sees that she has another message from the same gentleman. Opening it, expecting a standard “you too” response to her gentle rejection letter, she is taken aback by what she reads. The male user proceeds to go on an angry tirade. Citing that his profile made no mention of looking for a replacement mother and that the real mom was still on good terms with him, he was stronger for being a single father, and that Rosa was just a horrible person for being so judgmental. Rosa can only surmise what he expected to achieve out of such a rant. If it was to inspire her to see the err of her ways, it did. She never responded to anyone she wasn’t interested in again.

5. Ending Is Bittersweet

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Carla had found what many online daters find when she thought that finally a decent catch had landed. He was tall, handsome, intelligent, and an artist (notice a pattern?). His first message was laden with shared interests with in-depth details, asked the right questions, and provided key insights into who he was. Carla was smitten and quickly emailed back. This began what was thought a romance, Gmail style. The two were swapping messages five to six times per day for weeks. He sent her images of his artwork which, according to Carla, is very good and that she still has the pictures. In Carla’s mind they were a couple, although they had yet to meet. Finally, one night Carla suggests that they speak over the phone, grudgingly he agrees and what follows is an awkward conversation very different than what she was used to. Chalking it up to him being shy, Carla suggests that it’s time to meet and they should get dinner at the end of the week. He agrees and says to send him the details via email.

She writes an email instructing him to meet her at a favorite diner around six on Friday. Carla sent the email with high hopes only to have them shattered. The artist that captivated her, never responded nor did she ever hear from him again. This happened to her with a few more men and it gave her a complex, as if she was doing something wrong. What Carla didn’t realize was that she had encountered Bunkers. Those who cannot go on physical dates because they lead a sheltered life with room for one. It’s the typical BS of online dating users, lead on and drop off. Nevertheless, Carla knew she had something to offer, kept at it, and eventually met a great man. The two have been married for four years.

4. Well, At Least You’re In The Book

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Amber was a chronic dater. It’s exceptionally difficult to meet someone, even now that we are connected more than ever. The fact that there are choices not present before have made some hold out for something that doesn’t exist anywhere but in the minds of people; perfection. On a popular dating site she meets Dave, a budding writer who maintained a site to display his works, the two messaged and, oddly enough, Dave adds Amber to his website mailing list immediately following the conversation. After talking for a bit, the two go on an awkward first date where Dave seemed to not have manners, patience, or trust. He got up to use the restroom and took the arm-load of library books, his bag, and all his other possessions with him. As if Amber was not to be trusted with his few material items. Suffice it to say, she was not enjoying herself, so, she made an excuse and left. Later that week, Dave sends an email asking for feedback from the date and why she wasn’t interested. Strange again, all the same, she responds that she just wasn’t interested in him and that he experience good luck in the future.

A few days later, Amber gets an email from Dave’s site announcing a new story for view. Strange continues since the title of the story was coincidentally the same as the obscure saying she had worn on a button on their date. The story is written in first person (bad Dave!) and is paramount to a horrible display of a woman whom is referred to as a lesbian because of the way she dresses and how she constantly corrects people by shouting, “No, I just dress this way to repel men!” the story ends with this narrator character being beaten to death with a cricket bat. Amber knew what one would surmise, she was the lead character in this charming tale.

3. Always Google

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Sarah met an unusually interesting man. He had an unusual name and an unusual job. However, he was easy enough to find littered about the Internet. Amazon Wish Lists of stuff she couldn’t care less for and posts on Sci-fi nerd forums that made her cringe. So it goes, who is perfect? She decides to keep reading and give the guy a chance. She notices a Vanity Fair article link about the Menendez Brothers. She was perplexed that this link would appear in the search results of this man. What could one possibly have to do with the other? Sarah was fortunate that she showed keen sense and researched this deceptively charming man.

Sarah’s potential match had plotted to murder his father and concocted an elaborate plot involving mysterious foreign assassins. After a serious investigation that gained worldwide attention, the police found that the suitor had indeed been the murderer and he was arrested and placed on trial. His defence attorney was the same one that represented the Menendez brothers, hence the link. Although he was charged with involuntary manslaughter and served no prison time, his mother and sister had testified that the father was abusive, Sarah was still not interested. Curious though, she wondered what brought a murderer to eHarmony and then to her. What were the odds?

3. Information Overload

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Molly had a strong desire that plagues all women from time to time, she desired a sentimental, sweet, caring man that would tell her she was beautiful constantly, buy her flowers and shower her with affection. Prince Charming Syndrome. One day she gets what she wants. Meeting Eric is like a dream. He’s charming and sweet, sends her poetry and comments on her photos with empathy and gusto. After exchanging messages for some time, the two agree to go out and see what happens. Molly picks Eric up on a street corner downtown, he gets in and hands her a lovely bouquet of irises. She notices something creepy not long after. He is staring at her constantly and telling how she is much more beautiful than her pictures. Where some women might enjoy this, Molly was not comfortable.

They arrive at the restaurant where Eric proceeds to tell her his entire life story. Literally. Beginning with his birth in Mississippi, being Jewish, his family had experienced intolerable cruelty. Locals had burned crosses on his lawn, gave him and his family a hard time in town and eventually drove Eric’s mother to alcoholism. Life continued to be hard for him and by the time dessert came, he had reached the latest narrative of his life. College was just as hard on him, being haunted by his family’s past and caring for a mentally ill mother. He postulated that the world was full of hate and suffering and that it was best they go get a drink so he can relax. After hearing such a heartstring-pulling tale, although awkward, Molly just couldn’t say no. Consequently, at the bar, Eric proceeds to guide the conversation and ends on a Palestine vs. Israel topic that spirals out of control. Molly attempted to be diplomatic and said she didn’t know much about it but maybe both sides had a point. Eric exploded and began screaming at her and poking Molly in the chest with his finger. She asked him to stop and after a group of patrons intervened, Eric stopped. The two spent a blissfully silent half hour driving back home.

Eric got out of her car and they met at the trunk so he could retrieve his briefcase. They stood in awkward silence and while Molly just wanted the date to be over, Eric obviously interpreted the night differently. He actually leaned in for a kiss. Molly quickly pushed him away, got in her car, and drove off never to see Eric again. Consequently, while not her fault by any means, she drove that route feeling like a horrible person.

2. The Nerve Of Some People

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via wikipedia.org

Tim was out on a promising first date. She was wonderful and there never seemed to be a gap in the conversation. Everything is going great and Tim starts to think that online dating has finally paid off. Suddenly, Tim looks up and sees his good friend and his girlfriend walk into the restaurant. He waves them over to the table and they proceed to talk for about five minutes. The friend seems to notice Tim is on a date and makes excuses to leave the two in peace. Tim is happy that his date got to see him interact with others in a more natural way. However, when Tim looked over at his date, he noticed that her face was turned into a grimace.

She told Tim that she couldn’t believe the nerve of some people! How they could do such a thing! Slightly embarrassed, he begins to apologize for his friend and that it was only a few moments of quick conversation, the two were close— before he could finish his sentence, his date interjects with a comment that puts Tim in the rears as far as future dates go. His online match says she couldn’t believe how two people could date out of their own race. Tim’s friend was a black male and his girlfriend an Asian female. Tim’s date was a racist. Check please!

1. Walking Distance

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Rachelle had arranged to meet her online date not far from her workplace, where they would continue to walk to the restaurant for dinner. Grudgingly, she agreed, but on the day of the first encounter, she absentmindedly wears high-heeled boots. Stylish, sure, but, not very comfortable to walk in. Arriving at the prearranged corner, she meets Jack. There is some first-meet awkwardness and Jack suggests that they take the subway. More walking however, Rachelle is hopeful and agrees. He leads her off the train two stops before the one nearest to the eatery, claiming the walk will give them time to talk, mostly him. Rachelle is barely hearing what he’s saying. Her feet are throbbing from the boots and she is to the point of biting his head off not for being annoying, for being so damn hungry. Finally, they arrive at the restaurant and right before walking in, Jack declares that he is actually not all that hungry due to a late lunch. Rachelle is on the verge of snapping from screaming pain in her feet and ‘hangry’ mood swings. Then it dawns on her that she has an out. She gets ready to offer him a good night when suddenly Jack, again, interjects.

He suggests they go a few blocks more to a gelato shop he just adores. With a heavy heart, Rachelle agrees if only to bring this nightmare to an end. Walking into the shop she notices that it’s dark, quiet, and there are only two stools in the place. Close together and at the corner of the counter. Jack b-lines for the pair of seats and Rachelle lets out an audible sigh. When not violating her personal bubble, Jack is sampling literally every flavour of gelato the shop has to offer causing even more embarrassment for Rachelle and evil glares from the shop attendant. Rachelle turns her head and when she reflexively turns back— BOOM— Jack had planned the ambush kiss. In shock, she allows it to proceed for a few seconds before ending it. Then he casually turns to the counter server and orders one mango gelato, telling Rachelle they can just share. Flabbergasted by his forward actions she is stunned once again when the shared order arrives with one spoon which he begins to feed her with. Actually forcing the spoon through her lips.

Rachelle avoided the feeding by drinking her water at the rate of a long distance runner. Finally a friend happened to call and she feigned an emergency and without waiting for his response, flees as if for her life. Arriving at her friends apartment, she finally gets the boots off, eats real food, laughs, cries, and laughs some more. One more casualty of Onlineville’s dating scene. An example of why you might not get a return email and, on the other hand, maybe lucky to not get one.

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