awkward.

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.