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Embarrassing Date Confessions


Ever have one of those dates that you wish you could forget about? You can sympathize with our horror stories, too.

By Dee Anne Stiles

e all have those most embarrassing dating moments where we thought we’d just die at the time. You know, the ones that you’d find on some TV show called Candid Dating Bloopers.

Fortunately, time can tone what we thought were dating catastrophes down into those funny memories upon which we can look back and laugh.
The writing was on the wall. I just stood there stunned and turning red.
To give us a little, much-needed comic dating relief, your fellow singles share some of their most embarrassing date confessions here:

Mothers Just Know””
I really was excited about Sharon. I thought she could possibly be The One. I met her at the bookstore for a coffee. Who should walk by at that exact time and day but my mother! “Oh my, I always wanted my Johnnie to meet someone like you,” she said to Sharon. They then proceeded to have the best time talking about me and the family, while looking at family photos in Mom’s wallet. I eventually ended up marrying Sharon. How eerie! I guess mothers just know.

Cell Phones Do Tell””
With cell phone in hand, I sat at the restaurant table waiting for a first date, while firming up another new date with Cindy. That’s the one I was really looking forward to. Yikes, my date walked in 10 minutes early. I quickly got off the phone and set it on the table. Our meeting only lasted 45 minutes and we parted ways as friends. When I picked up my cell phone, I was shocked to hear Cindy’s voice say, “Hey, you are a nice guy. Thanks for bringing me along on your date.” I desperately tried to rerun everything I had said. Cell phones do tell when you don’t turn them off.

Putting a Damper on a Date””
I met Don through Match.com. Our personalities seemed to mesh OK and we were both Golden Lab lovers and owners. So, we had a few dates. Unfortunately, my 13-year-old Lab went to doggy heaven. My other dog, Missy, was melancholy. So, Don offered to bring his male Lab, Rusty, over to cheer her up. I guess you call it a double date. When they arrived, I had the barbeque smoking outside by the pool. Missy was trying to run away from hyperactive Rusty. I was fighting the new-friend-feeling for Don, as he cleaned the pool and chattered on. Suddenly, I heard, “Help me, I’m falling.” Don had backed right into the pool—clothes and all. Talk about putting a damper on a date. As he sat there embarrassed in my pink terry cloth robe, while his clothes were tumbling in the dryer, I found Missy hiding from Rusty under my desk. I took it as a sign for us both.

The Writing’s on the Wall””
I really do look 10 to 15 years younger. No one ever guesses my age. No one knows my real age except my family and the IRS. After awhile, I even thought I was 42, not 46. One day I finally found what I thought was and turned out to be my soul mate. The first time I had him over to my house, I gave him the grand
Oops! My graduation date revealed my real age.
tour. But this guy really was different. He was the only one sharp and thoughtful enough to really read my college diploma hanging proudly on my office wall. Oops! My graduation date revealed my real age. The writing was on the wall. I just stood there stunned and turning red. Luckily, we were only a few years apart and the small age difference did not matter in the long run. I’m an extremely honest person and it was the only thing I fudged on in my online profile since I really did look that age. It taught us both to be honest, yet open-minded. Had I not cut a few picky little years off, we would have never met our soul mates.

You Can’t Fool Mother Nature””
My hair was just starting to turn gray. Since I didn’t have time yet to learn how to color it, I would just quickly touch it up with my liquid eyeliner. One night, I met the most wonderful guy. We really hit it off. When he walked me to my car, ready to give me a goodbye kiss, it suddenly started to pour down rain. The makeup started running down my forehead in little black waterfalls. I just about died. He proved what a wonderful guy he really was. We both just laughed and he filled me in on hair coloring!

Saved by McDonald’s Drive-Thru””
I was nervous about my first long distance date, as I drove to the airport. We had planned to meet during her stop-over flight in my city. I had her picture, but no one matched coming through the door. Then, oh no! I spotted a vaguely similar looking person. But she was at least a 100-pound larger version of the photo. When we said hello, I felt like everyone was watching my face glowing red. She asked about going to dinner. I was scrambling about just what to do. My red face needed a break. Suddenly, I remembered the good old McDonald’s right across the street. I was never so happy to see a McDonald’s in my life and I took her to the drive-thru. We had a nice talk, she now realized the mismatch, and I had her back in plenty of time for her next flight.


Dee Anne Stiles is a freelance writer who has frequently contributed to Happen magazine.
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