10 F*cked Up Online Dating Stories

Sure, plenty of people have found love on the Internet. Some find promiscuous flings. Some even end up getting married. This article isn't about those types of online dating stories. This is about those once in a life time circumstances, when the person you meet online turns out to be a compete disaster of an experience, you know, once that "real life" thing kicks in.

Without further ado, I present the 10 most F-ed up online dating stories you've ever heard.

1. Quasimodo Needs Lovin' Too

Bobby Finstock from the Pointless Banter blog has had plenty of adventures in the online dating realm and fortunately for us readers, they almost always end up in disaster.

In one of ole Bobby's finest intimate encounters, he provides us with his hilarious night with a girl/it that he dug up from the Adult Friend Finder site.

"When we got to the restaurant my “date” got of the car and walked liked Quasimodo half bent over. One of her legs was severely longer than the other, giving her a very interesting gait. We went into the restaurant and ate, while the conversation was good all I could think about was that she was freaking me out a little bit."

Read the Full Story

2. Your 7th Grade Teacher

So, there you are filtering through a bunch of skeevy emails from a bunch of skeevy dudes all thanks to a prank. This is what happens when your best friend decides to post a casual encounters ad for you on CraigsList. Well this exact story happened to one girl and what she found was pictures of her 7th grade middle school teacher in her inbox. Yea it was awkward when she called him out on it, but after he offered to send her MORE pictures, then it just turned out-right F'ed up!

3. So... What's Your Sign Again?

While perusing the Plenty of Fish forums (always interesting) I found this little gem of an online dating story:

"The saddest (therefore, worst since I find all women nice in some twisted way) was a woman who showed me her X-rays on the first date. And I offered to take her to the hospital the next day, and then to a doctor's office not far from the hospital. She had terminal cancer. I doubt if she is still alive. I suppose I was the last guy who treated her to Chinese take-out."

Yikes! Talk about a weird situation. Not that I'm making light of Cancer or anything, but man that's one hell of a first date to deal with.

4. Missed Connection or Just Missed?

This little tidbit I found on the You Suck at Craigslist blog, which is hilarious by the way. It's not exactly an Internet dating story, really more of an Internet dating fantasy. Because really, what's worse than a creepy guy sending messages on an online dating site than a creepy guy who fantasizes about dating then posts it online?

Read the blog post here.

5. The Handicapped Hater

E from Geek's Dream Girl shares one of her weirdest online dating stories. The guy is pretty normal at first but then he drops a prejudicial bomb on her. Nope, he's not racist, not homophobic, he's anti-handicapped.

"Now, I can understand hating racists, rude people, the willingly ignorant… but the handicapped have no choice in the matter. You choose to be racist. You choose to be willingly ignorant. You don’t choose to be an amputee."

Read the Full Story.

6. You Want Me to Drink What?!

Like the previous story, this guy turned out to be pretty normal at first, even offered to buy the gal a plane ticket to come visit him. Every thing went great on their dinner date, which eventually lead to kissing, and then to the bedroom. Unfortunately this is where things started to go downhill. Apparently the guy turned out to be a self-righteous douche-bag and the night ended with the following:

"Then he says, 'you know what, if you can do this little thing for me we will work out and you can have all the credit cards you want. DRINK MY PEE, baby.'"

Read the Full Story.

7. The Shark Attack Girl

The video speaks for itself.

8. Well, We're Not Blood Related...

So you meet a real nice girl online, you have great chats, she has a sparkling personality and for some weird reason you get along like you were family. Oh yea, did I mention neither of the two parties had pictures on their profiles... so you can imagine the awkward moment when you go out on your first date to meet your sister!

Now granted she was only his step sister but that's still a little weird, right? Well apparently she was into it!

Read the Full Story.

9. Would You Like Some HIV in Your Coffee?

This one is just truly scary. Imagine that you've found the love of your life through an online dating site. You are really sure she's THE one. You finally fly across the Atlantic to meet her when upon your arrival, you find out that the love of your life is really a level 9 psychotic bitch. Here's what this poor sap had to deal with:

"I found a note on the kitchen table saying that she wanted me out of her house and if I didn't get out by midday she was going to call the cops. This is even though I had been cleaning her dust infested apartment and looking after her daughter. Next to this note she had also left another note which horrified me. She claimed she was HIV positive and that she'd been putting her blood in my milk and food."

Read the Full Story.

10. You Got the Right Stuff, Baby...

Jami from Date Wrecks has tons of ridiculous online dating stories but this one really takes the cake. Again, this guy starts out to be a completely normal nice guy in the beginning but by the end of the story you can't help but feel bad for how pathetic the guy is. Here is one text message she got from him after their third date:

“I want to turn into a metal monster and pierce you with a drill penis killing you and having to assimilate with me so we can be one.”

Wow, just wow!

As you might imagine, this sends up a major red flag. The worse part is that trying to get rid of the schmuck just makes things worse, to the point where he sings New Kids on the Block into her voice mail. The actual sound recording is in her post.

My summary isn't doing this any justice, just go read the full shit show right now.

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If anyone can beat these 10 stories then please post your messed up online date in the comments or shoot me a link to the article.

My Cougar Dating Story

One year ago...

She's sitting down the bar twirling a tiny straw around in high ball glass of what I presume is a gin and tonic. She's got a tight body and is all prettied up with make-up, hair and a sexy outfit, a bit overkill if you ask me, well at least for being in a small dive bar on a Tuesday night. She's definitely older than me, probably in her early forties, about ten to twelve more years than myself. She keeps making eyes at me; those extra long stares, some people might call it the "fuck me eyes," but whatever it is I know there is definitely some attraction.

I flash her a few smiles and acknowledge her flirtation. At this, she rises from her bar stool and walks directly over and sits next to me. Her legs crossed in a way that exposes her upper thigh and her cleavage stretching tight against a thin black blouse. She immediately opens up to conversation, introducing herself and exclaiming how she never approaches guys at bars like this...yeaaa right! It's at this moment that it dawns on me. She is on the prowl. Oh my god, it's a cougar!!

I had often heard many great cougar dating stories from some of my more sexually active college friends, stories that seemed beyond the realm of possibility to me, but tonight it looked like the cougar was finally attacking my scrawny nerdy boyishly handsome self... alright maybe I'm embellishing a bit but hey, I look young!

By the way, for those that don't know, a "cougar" is a slang term for an older woman who pursues and dates much younger men, with the age disparity usually having a gap of at least ten years or more.

The cougar dating scene has really only become in vogue recently, within the past decade, as previously this type of behavior was taboo or socially unacceptable for older women at the time. However, now cougar dating is almost catching on as a fad. It seems to evolved to the point where it's a sign of power and individuality for those older women. Some of them are divorcees simply looking to have fun, not ready to settle down again. Some are high powered executives who are more dominant and looking for a boy toy. I can't really say where the term cougar came from but it seems to fit well as a metaphor for this type of womanly behavior.

Ok, lets get back to my story...

Finally, after she buys me multiple rounds of drinks and we have a lengthy yet flirtatious conversation, we end up back at my place...yadda yadda yadda... I now have my own cougar. Well actually she has me.

The next couple months go great. Basically she calls me on random nights when she's feeling energetic, it's always on her terms, but the best part is she always buys when we go out, or brings me beer or wine when she comes over. It's almost like have a sugarmama I suppose.

Whatever type of relationship we have, it's certainly not a serious one and it can't last. And as with most cougar dating stories this one ends up with an unemotional and mutual ending. I can't say that it was one of the most meaningful relationship I've had, it wasn't at all, but holy shit, the sex was fantastic!

Present day...

So that little gem of a story occurred well over a year ago now. I'm not really looking for anything like that now. I really want more of a committed relationship a little closer to my age range, which is why I am still scouring the online dating scene. The experience was certainly nice though for a little fling and I learned a lot in the bedroom as well, which really helped me out. So in that respect, for you single younger guys out there looking for a little more experience I actually recommend finding yourself, or at least being prey, to lovely older woman.

There are even niche online dating sites popping up these days devoted particularly to cougar dating to help make the process more efficient. Hell you could probably even find plenty of them on free dating sites like Plenty of Fish if you look hard enough.

The Unsatisfied Women of Plenty of Fish

I've been searching around various different blogs lately trying to find different people's experiences in using PlentyofFish. Lately, I've been stumbling across some blog posts by some women who are out in the dating scene looking for potential male suitors. Unfortunately, it seems like a lot of disappointment in the men on the site. And for the most part, these men are making a lot of the common mistakes that I've mentioned repeatedly on this very blog. Lets take a further look at two of these examples, shall we?


The Saving Diva

Saving Diva setup a Plenty of Fish profile and has commented that she receives many short lame messages containing such subject lines as Hi, cute pic, etc. as I've discussed in my post about sucky subject lines.

"One guy actually referred to me as "sweetpea." I haven't been responding to the majority of the messages, and I haven't received a decent message yet. Is this how all online dating sites are? If so, count me out! I need a little effort put into a message."

So far though, she has actually gone out on a number of dates with some guys she met on Plenty of Fish. However, it was apparent that not all went well; below are a few of the men's dating faux pas:

• A couple of guys ended up lying about their height and were shorter than described in their profiles
• One of these had questionable manners
• One guy lied about his age
• Another didn't look like his pictures
• and a couple of them were quite boring

So, as we can see, the selection of decent guys on the site are few and far between, though her POF date#3 seemed to be a winner despite owning a Porshe Boxster S (apparently that's a turn-off?)


Romi from The Year of the Chick

Romi had an excursion on Plenty of Fish back in October which resulted in some humorous blog posts, but she basically concluded at the end that all she found were duds. Along with Dating Diva, she also received a lot of crappy email messages:

"I find that every time I enter the site and cruise around, there are five emails waiting after only a couple of minutes. What this means of course is sifting through a lot of crap, such as: ”Hey baby”—crap, “Can I see more pictures?”—crap, “I want to make you my everything”—crap, etc, etc, etc."

I don't think she ever went on a date with anyone, but it's clear in her making fun of the ridiculous messages she got why she wouldn't or couldn't find a decent date on the site.

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So, it seems that these two women, who seem like great catches, just aren't getting the kind of quality game fish that you'd find on paid dating sites or in real life for that matter. This just goes to prove my theory that the competition between men on PlentyofFish.com is quite weak despite the incredible large quantity.

This is both good for those of us able to display interesting attractive personalities through the site but also bad because it makes it more difficult to stick out amongst the rest of the mackerels.

Also, it appears that both Saving Diva and Romi experienced the same thing I had when I set up the fake profile and received tons and tons of garbage messages with ridiculous short sited subject lines like; hi, hey, hello, etc.

Another problem that is pretty apparent to me is the lying. Now, that is something I just don't understand. When you setup a Plenty of Fish profile you have to realize that the intent is to eventually meet other people in real life. And when your first impression to that person is of being a liar then you are off to a really bad start. Chances are that there isn't going to be a second date and you basically wasted your time.

All in all, I am beginning to understand the frustrations of women on plentyoffish. It's like the guys aren't even trying. Seriously, these guys really need to start reading my blog...