Today I'm having one of my best friends tell us a story...

A story about a date she went on that I think tops them all.
Serious, folks.

You can't make this stuff up.
Without further ado, here is Lindsay's most awkward date ever.

The Most Awkward Date of My Existence

His name wasn’t Richard, but we’ll call him Richard.

Richard and I were casually introduced through a mutual friend at school and, as is the case with most acquaintances these days, he found me on Facebook.

We chatted fairly regularly. Richard seemed genuinely interested in getting to know me and thus created surveys for me to answer which included questions like, “What’s your favorite place to visit?” or “What’s was your favorite childhood activity?” I didn’t think much of this behavior and returned the surveys for him to answer as well.

Time went by and Richard asked me on a date. When the day came he picked me up at 5:30pm and we went to dinner. In the surveys Richard came to find out my inexpressible love for Italy, so he took me to Johnny Carino’s. I’d never been there before, but the food was delicious and conversation, though awkwardly deep at times, wasn’t completely uncomfortable.

After dinner Richard took me ice skating, having learned from one of his surveys that I enjoyed skating lessons in my youth. It was, again, fun and only slightly awkward at times. After we were done, I thought to myself, “That’s a good date. Dinner and an activity,” but when we got in the car Richard informed me that we were now going to his apartment to make dessert and watch a movie. I secretly groaned inside at the thought of a prolonged and mildly awkward date.

When we pulled into the driveway, Richard exclaimed, “Alright, this is the fun part. Now I have to blindfold you.”

“Uh…no,” I responded with a laugh.

“Yeah, it’ll be fun. Trust me.”

And, for some bewildering reason that I still don’t quite understand, I did. I let him blindfold me. He guided me to his doorstep and while doing so, introduced me to a whole new level of awkward. It was just plain uncomfortable, so I made sure that I could at least see out the bottom of blindfold.

I was then guided into Richard’s entryway where he told me to wait as he “got things ready”. Oh boy! Suddenly, an Italian melody began to play through his small apartment accompanied by a sinking feeling in my stomach. “What have I gotten myself into,” I thought. I shuffled and tripped awkwardly as Richard guided me into his family room.

“Alright, I have to pick you up for this part,” he announced.

“Um…what? No,” was my immediate response, to which he laughed and quickly ignored. He put his arms around me, my elbows bent and arms at my sides, and lifted me onto, what I thought was a LoveSac. One more moment of waiting and I was given the command to remove my blindfold. “Oh here goes nothing…” I thought.

I looked down and found that the LoveSac I thought I had been sitting on was actually a large inflatable raft in the middle of the family room floor. Richard stood at the front of the raft wearing an Italian straw hat and “rowing” us along with a plastic yellow ore. In front of us was a huge projection screen playing a video of gondolas riding through the canals of Venice. . . . . .

Speechless, mind-boggled and laughing uncomfortably I sat in that inflatable raft not knowing what to do. And then, without even a moment to catch my breath or orient myself, Richard pulled out his guitar and proudly announced,

“This is a song I wrote, inspired by you.”

“You wrote a song for me?!” I asked surprised

“No, inspired by you,” was the response.

I do not remember the words or the title or the melody of the song. I just sat there, mind and heart racing, wanting it to end. Wanting to wake up.

When he was done singing, I applauded politely and thanked him for all the work he had put into this…whatever “this” was. I was half expecting him to pull out a black velvet box and propose right then and there…but to my relief, he did not.

We then proceeded to the kitchen to bake a cake. When it was completed we took our servings to the family room. I instinctively went to the couch to have a seat, “Wait! Let’s sit here,” Richard said, ushering me to the inflatable raft in the middle of the floor. I reluctantly got up from the couch and sat next to him in the raft as we watched “A Goofy Movie” on the large projection screen.

When the movie ended, it was 12:30am. Richard took me home and gave me a hug. As I closed the door behind me I let out a long and relieved sigh…it was over. 7.5 hours later, it was over. Absolutely and unequivocally the most awkward date of my entire life.

I have to give Richard some credit for his outstanding creativity…but no, I never did accept another date invitation from him. Once was enough for me.

Thanks for the great story, Richard.

Thanks, Linds.

Anyone else have an awkward date story?
Please do share.


Sasha said...

highlight of my day.
this really made me laugh.

good story.

Chess said...

Holy crap! First dates should NEVER be that long. Like, maybe 3 hours at the most. Good story though, I have never cringed so much in the two minutes it took me to read that! Hahahaha! :)

Cat said...

and i thought my last date was awkward.
that's hilarious! (:
at least he really put a lot of thought into it!

Whitney said...

I can't believe that I've never heard this story!! Oh. my. awkward. He's sure creative...

Leon said...

I don't have any stories, but I bet if you asked the girls I've gone out with, you'd get some good ones.


Fashionably Kate said...

Oh my goodness.

That's SOOO awkward.creepy.nice.CREEPY. weird.

Thanks for having her share that here!

and GORGEOUS new header of you! ;)

CAPow said...

wow. i've got nothing that tops that! awk---waaaaaaaardd.....

Adorably Distracted... said...

omg! If i were her I probably would have RAN at some point! lol I can't stop laughing though

Nicole Smith said...

Wow. so funny! Thanks to your friend for sharing.

amourissima said...

I didn't think it could be done but this does top the "worlds most awkward date EVER"

Too much waaaaaaaaaaaay to soon.

Michelle said...

Oh my goodness!! That is like 3 dates jammed pack in one. Dates, I might add that *could* be cute, say, Oh I don't know, NOT on the first date!!

Poor girl, 7.5 hours!!

Sounds like the best thing she got from this date was the story about it.

Shayna said...

Oh my goodness, talk about long. So terrible when they are long. The majority of my group dates in high school were at least eight hours but at least I was in a group. I do have an awkward date story though.

First one on one date (if it could be called that) I lived about an hours drive away from any events, movie theaters, shopping etc.

The kid that asked me I had known since elementary school but didn't really talk to much. We were going to a rodeo. That's not a bad idea, but the rodeo was an hours drive away. That's two hours to and from where we were just going to be sitting doing nothing in potentially awkward conversation. We left at 6:00

There were a few quiet spots and awkward pauses and his hidden meanings of what we were (friends, friends with potential{oh boy} boyfriend girlfriend{please help}) First date, not even close friends, I only went over to his house a couple times when we were little because I couldn't be left at home alone. Luckily that conversation was quickly swatted out

Then I found out that we were meeting his MOM in the town right before going to the rodeo. We got into her car, while he sat in the front seat with me in the back talked to her. It was a good thing I knew his mom before otherwise it could have been way more awkward.

The rodeo was nice and we went to dinner at a 24 hour truckers cafe, his mom paid and we were taken back to his car. However we didn't go home, it was 11:30 and we weren't heading back home yet which if we left then we would have gotten home at 12:30. We went to Walmart where he insisted on buying a book that I was going to buy myself.Then we went to his coworkers family's house and spoke to them as they doted about me to him while I was standing on their porch in front of them. They never complimented me personally, but they complimented me through him, as though I wasn't really there. Extremely awkward hour, yes an hour of this so you can imagine I didn't get home until 2:00.

When I compare it to other stories I have heard it isn't quite so bad but it was long enough and awkward enough to be on the top of MY awkward date list.

And he did ask me out two times after this. I only said yes when it was for a dance and would be an actual group date, but we still drove that hour drive by ourselves.