Worst Dating Story Winners

I had so much fun reading (and wincing and squirming) your worst dating stories that I decided to share the winning stories here with you. These three were pretty terrible, but luckily turned out for the better. Many thanks to everyone who submitted their tales and misadventures. I applaud you and your willingness to share. Now as they say, read 'em and weep. (Tears of laughter, that is.) From Kasondra:
When I was 19 I went on a date with my highschool sweetheart (who is now my husband). He decided to take me out to eat, and then do a little shopping. Well, our shopping experience was QUITE THE EXPERIENCE. My husband is a huge hunter and loves anything that is camouflage. He asked if it would be ok if he would do a little shopping in Sportsman’s Wearhouse. I kindly said yes, that it was fine. We went into the store. Everything was fine; he was looking around at all of the good things he wanted to buy. But then out of no where he saw something for me…. any guesses? Yes, a camouflage two piece swimsuit for--you got it--ME! So, trying to be a good sport I told him I would try it on. I went in the fitting room and tried it on (surprisingly, I didn’t actually think I looked too bad). I came out and he LOVED it, so he said he wanted to get it for me! So I went back into the fitting room started to get my street clothes back on and out of no where the lights shut off in the entire store! I got the rest of my clothes on quick and my boyfriend and I start to look around as to what is going on. We could not find a single person in the store. The store had closed down with US IN IT! Some might say this could have made for a fun night. Well, it could have been. We could have gone to the camping section build a tent, ect., but my husband heads to the front of the store and the ALARMS GO OFF! I thought, Oh boy, now we are in trouble! All I had wanted to do was have a nice evening and now we are going to get in trouble. My husband was still walking around with the swimsuit he wanted to get for me and I told him to put it down, that they were going to think we were trying to steal something. But he wanted to buy it still! Someone finally showed up, got us out, and he was even able to buy the swimsuit. All for trying to make him happy in my camoflauge two piece!
From Carol:
This is a bad date story with a happy ending. I had met someone through a mutual friend and he asked me to lunch on a Saturday. I said yes and he said he would pick me up at noon. He picked me up and said we just had to make a stop along the way. We ended up at the airport, and who was waiting at the curb but his mother! She introduced herself and said she had heard a lot about me and said she was looking forward to lunch?!?! Apparently he invited his mother along to our lunch date. Well, we all did have a great time, mother or no mother, and we are now happily married for 10 years!
From Robin:
My worst date ever happened on New Years Eve 2006. My date and I were supposed to meet at a lounge. However, I mistakenly gave her the wrong address. An hour later she arrived and we grabbed a table and started drinking. Just before midnight I needed to use the restroom. Then I realized that I had had too much to drink and vomited all over myself (shirt, pants, shoes). I cleaned the shoes and pants as much as possible. Luckily, I had on an undershirt that didn’t have holes in it. I got back to the table now after midnight and she immediately noticed the smell. I have no clue why but she hung around. After the lounge we decided to get coffee at the doughnut shop next door. We got our coffee and sat at a table. What appeared to be a homeless man entered the shop and sat next to us and started a conservation. There were two problems: he was obviously crazy and he smelled worse than I did! I tried moving, but he followed us. Finally, we decided to go for a walk on the lake front, but by that time it was 6:00 a.m. That wasn’t the best idea, since we were in Chicago and the air temperature was -2. We were both freezing and could barely talk. At that point we called it a night. I walked back to my car and had a blissful end to my horrendous night….a parking ticket! I still don’t know how, but that woman is now my wife.
You can read all of the other entries in the comments section of the original post. Congratulations again to our winners, who have received delicious gourmet gifts from Mrs. Fields Gifts. Have a happy holiday weekend, everybody, and may all your stories end up sweet! {Image via Pinterest.}
Back to blog