Computer love

Your best and worst online dating stories

By - Feb 11th, 2011 04:00 am
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In the 80s, there was video dating (as hilariously evidenced above). After that came singles chat lines (on real land line phones!) and then the proliferation of online dating sites and Craigslist personals. We’ve all heard of and eHarmony, but there are plenty more where that came from: OkCupid, PlentyofFish, Zoosk, and JDate, to name a few. Millions of people are currently signed up on one or more of these sites, and surprisingly, 1 in 5 married couples met online according to recent stats.

There are plenty of success stories when it comes to e-dates, but anyone who’s been on a blind date knows that it’s not always a pleasurable experience.

With that in mind, TCD polled our readers and eNews subscribers for their best, worst and most hilarious experiences with online dating, and boy did they deliver. Their stories ran the gamut from touching to terrifying, with tales of public urination, one man’s personal mission from God, and even a few marriage proposals. Read them all, and then vote for your favorite in the comments section. The top two vote-getters will receive these amazing prizes:

#1:A high tea for 8 at Anaba Tea Room

#2: Two tickets to the Florentine’s Italian Girl in Algiers, running March 18-20, and $25 to spend at Via Downer

Votes will be collected through Sunday, Feb. 13, and winners will be announced on Monday, Feb. 14.

And now, without further ado:

The Worst

Entry 1: Sweatpants, earwax and ex-wives
Submitted by EJP

When my online date got out of work too late to make our planned yoga class, we decided to meet for the first time at Pizza Man for a drink instead. The pictures he had shared had to have been from at least 10 years ago and he had obviously lied about his age, making him probably 15 years older than me. Apparently having already changed for yoga, he was wearing sweatpant-fabric athletic shorts with his white button-down work shirt.

He spent the first 10 minutes on his phone (I kick myself for not just leaving then) and then proceeded to blather on about how much money he made (yet he tipped the bartender like 5%) and how he wished his ex-wife would get hit by lightening because she was such a “f&*%ing c&*t,” (yep, he said the C-word… several times), all while digging around in his ear with his finger, periodically taking it out to look at what he had found in there and flicking it away. If there had been a back door at Pizza Man I would have used it. Later he texted what a great time he had and that wanted to hang out again.

As sexy as his black socks and ear wax were, I never saw him again.

Entry 2: Saved!
Submitted by Iambabachu

At one point I decided to put my hat in the ring of online dating services. I was looking for an artistic person, with joie de vivre. I did find a legally blind film maker and a nearly deaf folk singer. But the best/worst was this fellow, a musician who seemed interested in many of the things I had mentioned in my ad:  art, music, community, poetry and spirituality.

We arranged a meeting at a local coffee house. As it turned out, he was not a musician, he was a janitor. He did sing in a rock group at his born-again Church. After trying to convince me that I would go to hell if I did not accept Jesus as my personal Lord and Savior, he gave me a compliment that sealed the “no” deal.

He said, “If you were a man and you had blonde hair, I would swear you were Barry Manilow.”

At that point I excused myself. As he followed me out to the car, he asked “Does this mean you don’t want to go out with me again?” A resounding yes was my response. The only yes of the evening.

Entry 3: Bathroom Break
Submitted by Mark R

I traded emails for a couple weeks with a woman on She lived in Kenosha and I lived west of Waukesha, so when we agreed to meet finally, we met at a Texas Roadhouse near Kenosha for dinner. She picked the date, and it turned out it was her birthday (which she didn’t tell me ahead of time).

After her spending an inordinate amount of time ordering and sending back her first order because she didn’t like it, we finally got our food. Conversation was pretty normal while we had cocktails before dinner, so it seemed to be going well. Otherwise we each shared the normal first date info about ourselves and families. After dinner, we sat at the bar for a drink. She talked of getting together again. As soon as she finished her after-dinner drink, she said she had to go to the restroom.

Then she grabbed her coat, put it on, and reached for her purse. She informed me that she never uses public restrooms and had to go home in order to go to the bathroom! We exchanged phone numbers and she clearly “had to go” so the end of our date was pretty sudden.

A couple days later, I got an email that said she liked me and wanted to get together again sometime, BUT she was going on vacation for a week, with her parents (we’re both in our 40s!) and would be in touch when she returned. I never got a call, didn’t pursue it, and wasn’t really interested when I reflected upon her somewhat weird behavior at dinner.

A couple months later, I got a message from her on She said she liked my profile and acted like she had never met me before! Can anyone say “outer space?”

Entry 4: Dating Under the Influence
Submitted by D. Wankowski

I met this girl on a dating site and we decided to meet at her house near Kenosha. Our date was for 7 p.m. and we were going to a haunted house. I arrived on time and called her from my cell.  She said she was at a friend’s house. Twenty minutes later she calls me and says “Hey can you pick me up a few houses down? I don’t want my Dad to know I was driving.” I asked “How come?” and she said, “Well I got two DUI’s in the last 6 months and I don’t have a license.”

Good thing I was driving.

Well, on the way she was drinking an energy drink with vodka, which I thought was all energy drink. By time we get to the haunted house she is half in the bag. We park the car and she asks if I mind if she takes a pee outside. She squats down, puts her butt on the bumper and pees. We get in line for the haunted house and she repeatedly says to me (and everyone in line) she’s so scared she’s going to poop her pants. She also decides it would be funny to make fun of people in line by asking them “if they think they’re cool.”

After the haunted house we’re driving home and she asks if I wanted to stop for a drink or two. All I could do was laugh and say, “No thanks, I have a long drive.” At this point she was obnoxious-drunk and furious that I didn’t want to go to the bar with her. I pull up to her house, she asks me again if I want a drink, I say no. So she gets out of the car, slams my door, hops in her car and drives off.

Entry 5: Meet Me at the Food Court
Submitted by Sarah from the ‘sha

This is a story of a man that hid behind his computer. I chatted with this gentleman on the dating site for a few weeks, getting to know him and exchanging friendly questions. The conversation was excellent so I asked to meet at a coffee shop in Waukesha. He suggested the food court at Brookfield Square “‘cuz coffee wasn’t his thing.” When I got there, he already had himself a soda, didn’t offer me one or give me time to get one and we sat down to chat. Unfortunately the conversation (I’ll use that word lightly) was one-sided with the occasional intercessions of “yep,” “nah,” and “mmhmm” from him —  I never got a response greater than that and never was asked a question.

He drank his soda and stared at me with a contented look on his face. I stared at the Cinnabon clock hoping for time to go by faster, and when I couldn’t handle it anymore I politely told him I had errands to run. He then said it was fun and would love to meet again. (?!?!?!) I booked it from the table. I had better interactions with the people walking by our table than my date. Needless to say there was never a second date.

The Best

Entry 6: What Happens in Vegas
Submitted by S. Crocker

I hate filling out profiles, so I fill them in with smartass replies, maybe in an attempt to make myself seem clever and nonchalant. So, when updating my OkCupid profile after the end of my first marriage, I finished the profile section: “I spend a lot of time thinking about…” with the reply, “Monkeys on roller skates.” Amazingly enough, it was the door my future love would later need to send a message. He appreciated my monkey comment, and ended with “at least it’s not an evil monkey in your closet.”

After perving his profile, I thought, “Hot, and a Family Guy nod? Score!” We started chatting, and spent many nights having virtual pajama parties, staying up far too late. We finally met face-to-face, and have been inseparable since. We are getting married March 12 of this year (in Las Vegas, a vampire-themed wedding!)–3 years since we first met face to face. We both thank the monkeys every day for helping two dorky souls find each other online.

Entry 7: $79.95 well spent
Submitted by Susan

Here’s what a 6 month membership with got me:

-18 messages from creepy and unattractive males living more than 300 miles away who wanted to know “how I liked it”

-12 awkward coffee dates which gave me great relief once over

-1 date who was already sloppy drunk when I showed up to meet him… at 6p.m. on a Tuesday

-2 guys who would text me non-stop as long as it was after 12 a.m.

-1 date with a married man (which I wasn’t aware of prior to the date)

-30+ searches on CCAP to weed out the “legally challenged”

-4 hilarious tales of caution for any of my friends who have considered online dating

-2 phone numbers in my phone that I won’t delete so I know when NOT to answer

-2 2nd dates that I thought could “really go somewhere”

-1 fiance who I will be marrying on Sept 17, 2011

Best $79.95 I’ve ever spent.

0 thoughts on “Computer love: Your best and worst online dating stories”

  1. Anonymous says:

    I vote for #3

  2. Anonymous says:

    Voting for – Entry 6: What Happens in Vegas 😀

  3. Anonymous says:

    I vote for #3

  4. Anonymous says:

    I vote for #1!

  5. Anonymous says:


  6. Anonymous says:

    I vote #1

  7. Anonymous says:

    Best story here! Outer space is right…I would have taken her out again to see how long it would take her to remember your first date!

  8. Anonymous says:

    #3! Poor bathroom skills and TMI – everything a bad date needs!

  9. Anonymous says:

    Earwax is tough to beat, but leaning on the bumper and peeing outside a haunted house… really, she should have waited for the second date for that. I vote No. 4.

  10. Anonymous says:

    #1 wow. just, wow.

  11. Anonymous says:

    Outter space 4 sure. Do you still have her # or do you call the County jail?

  12. Anonymous says:

    Number 3 for me. What a trip!

  13. Anonymous says:

    Wax on, wax off. I vote for #1!

  14. Anonymous says:

    I vote for #3

  15. Anonymous says:

    Number four for the drunk bimbo.

  16. Anonymous says:

    I also think number four is the winner. Good Lord I agree with Strini, what the hell?!?!?

  17. Anonymous says:

    I kinda respect a woman who doesn’t use public rest rooms.

  18. Anonymous says:

    Earwax and black socks with shorts – every girl’s dream date! I vote for #1!

  19. Anonymous says:

    Some good stories, but the best one is #3. Curious what she ordered for dinner – what is it that they like to eat on “V”?

  20. Anonymous says:

    OMG!! These are funny, but my fave is #3!

  21. Anonymous says:

    I’ve seen one very burly, imposing, agressive woman in her early 70’s who connects online with men by the hundreds. She meets them one after another, sometimes from out of state and is quite giddy about each “new one”, but every single time shortly thereafter she says that she sends them away. She is a tall woman, and her cup size is enormous, like two cannons proudly encased in an iron bra, and she says that her bedroom is very well kept.

  22. Anonymous says:

    Awwww, #7! Yay for happy endings!

  23. Anonymous says:

    I love #7 that’s my vote! True, Hilarious, and Heart Warming!

  24. Anonymous says:

    #7 for sure. Cute and hilarious.

  25. Anonymous says:

    #7….that’s exactly what online dating is like! But it’s so great when it works out = )

  26. Anonymous says:

    I vote for #7 because of the realism, balanced simplicity and informativeness.

  27. Anonymous says:

    #7 hands down is the best…lol

  28. Anonymous says:

    #7 gets my vote…for perseverance alone! I love a happy ending. 🙂

  29. Anonymous says:

    Gotta love #7.

  30. Anonymous says:


  31. Anonymous says:

    #7 rocks!

  32. Anonymous says:

    I vote for # 7.

  33. Anonymous says:

    #7 for sure!

  34. Anonymous says:

    I’m the lucky fiance in 7, so I guess that’s my favorite!

  35. Anonymous says:

    #1 for c-bomb usage!

  36. Anonymous says:

    I vote for #7!! Tyin’ the knot!!

  37. Anonymous says:

    Love #7 The sheer agony of it all, then, perfectly-a Happy Ending.

  38. Anonymous says:

    I vote for #7. It’s valentines day and I love a happy ending!

  39. Anonymous says:

    Hands up…..#7.

  40. Anonymous says:

    #7 all the way

  41. Anonymous says:

    I vote for #3. At least it wasn’t in Waterford!

  42. Anonymous says:

    i would like to vote for number 7. thats a good number

  43. Anonymous says:

    #7 She is tenacious.

  44. Anonymous says:

    Vote for #3. One of two possibilities. At our age, an untimely leak in her colostomy bag or, she knows she can’t stay awake much past dinner, you’re going to have to pee three or four times an hour anyway, so she’s just trying to get you back to her crib by killing two birds with one stone. She’s a keeper either way. Always keep a spare bag in the car MR…

  45. Anonymous says:

    #7 is DA BOMB!!!!

  46. Anonymous says:


  47. Anonymous says:

    Vote for #1. What a DB!

  48. Anonymous says:

    Voting for #3—all I can say is OY VEY!

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