What are some of your most awkward dating encounters or weird former relationships?

My mother used to date a local blues musician who also gave guitar lessons on the side. A girl my mother worked with wanted lessons, so she would come over from time to time for about an hour and made horrible attempts at playing Bon Jovi on an acoustic guitar. I would always make a point to "drop by" to chat to her as I found her attractive and funny.

One night we all agreed to go out to a local jam session in Lockport. While there, I get up to order a pitcher of beer for our table from the bar. Walking back to the table, I trip on the leg of a chair and dump the entire pitcher onto the lap of the poor young lady.

We've been together 15 years, married 8.

When is the divorce?

_________________
You do not talk to me like that! I work too hard to deal with this stuff! I work too hard! I'm an important member of the CSFMB! I drive a Dodge Stratus!

When she sobers up.

This isn't a relationship but it was plenty awkward. My friend was dating this girl and I was out with the two of them and the girl's best friend who was this cute little blonde. Of course I was trying to get up on the friend. She was wearing a necklace with a oddly stylized initial of her first name. It was pretty cool so I mentioned it like, "That's a very interesting thing you've got around your neck." She suddenly got all weird and walked away from me. I was like, what's up with that?

Later on, I was asking my friend about her. He said, "Yeah, she's pretty hot, but she has that crazy birthmark on her neck." I hadn't noticed, but I was absolutely mortified that she actually thought I would be so rude. I still feel bad about it thirty years later.

_________________
Freedom is our Strength.

Similar. While a college freshman, I got this chick to go on a date with me one Friday night. By the time we went out (7 pm), I was already wasted. Knocked a pitcher of beer onto her (white) coat. Later, in an attempt to be funny, I broke the screen on one of R & R's (the local bar) tvs. We kind of had to sneak out of there. Six years later, I got a second date, and several years after that, we done got hitched.

Look, I can't ignore everything.

When I was 20, I started dating my bosses ex behind his back. They had a kid together too. She was hot and it was fun, but it a total dick move on my part.

_________________

+

_________________
There are only two examples of infinity: The universe and human stupidity and I'm not sure about the universe.

Now this one has potential.

_________________
Power is always in the hands of the masses of men. What oppresses the masses is their own ignorance, their own short-sighted selfishness.
- Henry George

Go check Spaulding's "All Me" thread cuz I told my story there not noticing this thread.

_________________

Yep. Like Punch said, that's the way to do it!

_________________
Freedom is our Strength.

I wasn't looking at his neck, man.

_________________
Good people drink good beer - Hunter S. Thompson

<º)))><

Waiting for the time when I can finally say
That this has all been wonderful, but now I'm on my way

So back in the days of ICQ I used to do naive things like search for chicks within a 50 mile radius who listed aphex twin or drum and bass as an interest. Once I found a 14 year old jungle/drum-n-bass DJ chick who introduced me to Tim who introduced me to his friend Chicago underground rapper robust, but that's another story for another day.

One night I found an ex/raver chick named Katie who went by Bubbles (from the Powerpuff girls I think?) and even tho she was from naperville or sonething she was down at UIUC. We got along extraordinarily well and she'd be up all night studying and I'd stay up all night cuz I'm convenient like 7-11 and we talked for weeks at least, maybe months, it's been awhile.

Anyways my old friend Justin (he's the guy who grabbed the dope.org DNS years ago) was down at UIUC with his then-girlfriend CJ and he was like "dude you gotta come down and meet this chick... Hell our guy Tet is having a birthday party and harvesting two pounds of blueberry (weed) for his birthday party that I'm DJing... Come on down!" --- how can you turn down a properly cheeched night soundtracked by DJ SCSI? down.

So I get down there and meet ol girl and when I first meet her IRL she checks me out head to toe and immediately tells me she's a born again ex-raver who doesn't believe in sex b4 marriage anymore. Undeterred I still had a picnic with this chick, baked cookies with her,and you know what my thanks was? When the party was starting up she tells me we have to leave cuz she's having raver flashbacks, so she drags me to a couple of other more alcohol-centric parties (???) and then we ultimately sitting in a desolate house with her friends.... Spun out tweakers coming down from a night of coke/meth/whatever.

Seriously it was fucking depressing to realize my original plans had us high as hell listening to awesome techyes with quality people.... And here I am sitting in a quiet desolate room full of miserable druggies. At least be happy/fun druggies, you know?

Ol girl fucked off the next day and basically never talked to me again. I was able to catch theaftermath of the party I missed the next day, with Justin busting my balls like "dude that pussy better have been good... You missed out" still, I made up for lost time by eating 2-3 pot brownies smoking a couple hitters of keef (weed/THC crystals shook off of the long leaves of the pot plants) and smoking some shit. I got so thoroughly stoned I was still stoned when I got home to elk Grove having driven back from Champaign (I didn't have/smoke anything in the car on the way back) thank you pot brownies!

As for ol girl, well, I could and would do much better so hey at least I got a story out of it huh?

_________________

Pretty much.

_________________
Freedom is our Strength.

I see absolutely nothing wrong with this. But don't go by what I said, my awkward dating story is dating my wife's roommate before her.

_________________

Ah, the Switch. In the Middle Ages you coild get locked up for even talking about it.

_________________

They didn't have roommates in the Middle Ages.

You slay one, and then you go after her friends. You are a true swordsman.

_________________
Good people drink good beer - Hunter S. Thompson

<º)))><

Waiting for the time when I can finally say
That this has all been wonderful, but now I'm on my way

Jennifer Nelson was my first kiss in 7th grade. Her father murdered her and her five siblings later that year.

_________________
Sex isn't dirty, sex isn't a crime. It's a loving act between two or more consenting adults.

-Hank Kingsley

I’m glad someone spiked that set up.

_________________

To be fair I did wait two years and dated their suitemate before asking her out...and pawned the original girl off on my roommate (they got married).

_________________