Love Connection……NOT!
There are so many dating shows on TV. From Love Connection, Blind Date, elimiDate, The Bachelor, The Bachelorette, Temptation Island and many others.
Most of us have funny dating stories. Most of us didn’t meet Mr/Mrs right in high school like my sister was lucky enough to do. Therefore we have probably gone on our fair share of dates. It is safe to say that most dates don’t work out. I am not suggesting that they are a disaster, but clearly finding that someone special takes time, effort and unfortunately many dates.
I have a number of single friends who share their dating stories and I must admit some of them are hysterical. Since most–if not all of us–have had bad dates or funny dates, I think it’s time we should share them. Feel free to change the names to protect the innocent.
And of course I will go first:
One of the funniest dates I ever had was way back in 1986 when I was living in Massachusetts. My travel agent (remember when we all had one) had a new employee that was moving in from out of town and asked if I would take her out and show her around. We decided to go out and actually play tennis at the house she was staying at which was located in Sudbury, MA. And yes they had their own tennis court, pool and hot tub – gorgeous house. Anyway after playing tennis we had decided to have a BBQ. But of course I forgot something at the store and needed to run out quickly. As I left the house it started to pour and as I walked to my car I could barely see three feet in front of me. I got in my car and instead of continuing around the circular driveway (like a normal individual) I decided to back up. Not a smart move, since it was pouring and I couldn’t see a thing. The next thing I know I hit a beautiful and expensive light post which came crashing down and shattered in the driveway.
So let’s regroup and see where we are at this point.
- I am with a total stranger
- It is pouring out
- I just left huge marks on their nicely manicured lawn
And I hit and shattered a light post!
Not a great start to a relationship. Anyway the end result was after I returned from the store I apologized and offered to pay for the light post.
No there wasn’t a second date.
I hope you enjoyed my story and I really look forward to hearing yours!
AND WHO KNOWS…THERE MIGHT BE A PRIZE FOR THE FUNNIEST STORY!

August 8th, 2007 at 2:00 pm
What a way to make an impression Merrill!!
My funniest date happened in high school. A guy I met from a different high school asked me to his prom. We went to the dance and he had told me he was a fabulous dancer and that I was in for a treat to be able to dance with him. He knew I loved dancing so he really talked up his skills. Once on the dance floor, he had no concept of his dance space vs. my dance space!! He was dancing spastically and his knees kept bumping into mine. I kept backing up to try to avoid the bruises I was envisioning would appear the next day, but to no avail. He kept moving forward and I kept backing up. We must have rounded the ballroom floor 10 times during one song. After the one dance, I asked to go sit down and get something to drink. It was a very long prom night!!
August 8th, 2007 at 3:59 pm
I was on a double date in high school and the boy of the other date had brought a 6 pack of corona with him on this date without my knowledge. well, after our movie we went to the McDonald’s where everyone who was anyone hung out… we were all talking in the parking lot when a police officer showed up. i wasn’t worried because none of us had been drinking and we were not doing anything wrong. then the officer said, “who drives the white ford escort?”. that was me. Next thing i know i am in the manager’s office of the McDonald’s with the police officer and the store manager and they were threatening to call my parents.
Some how i talked my way out of the situation, immediately went outside, explained to all of the people on the date that they were finding their own way home and never spoke to either boy again.
August 9th, 2007 at 5:23 pm
Well this is a fun blog topic!
When I was in high school, one of my boyfriends ran over our mailbox. My parents have a very long, tree-lined driveway. My dad had made a little turnaround, so we wouldn’t have to reverse all the way out, but for some reason he never ever used it. Well, this one night he was leaving and he took the mailbox with him. Of course, my whole family was watching.
August 10th, 2007 at 10:31 am
I was going on a first date with a guy my junior year in high school and he lived in our neighborhood. When I told my dad I had a date, he said ‘as long as it’s not the guy who drives that little yellow car that speeds through the neighborhood’. Yes, it was the guy who drove the little yellow car but I didn’t tell my dad that. I thought we would be sneaky and when he came to pick me up for our date, I had him park away from our house. Of course, my dad wasn’t fooled and said something about it the next day.
We continued dating and when it came time for prom I told him that my parents wanted to take some pictures before and he reluctantly said ‘just a few pictures and that’s it, no big deal’. Well, my dad just happened to work with a guy whose girlfriend was a professional photographer and on prom day, they came over and set up a backdrop in our front living room for before prom pictures. I knew they were coming to take pictures but not with a backdrop! When my date came to the front door to pick me up, I told him ‘come in for a minute for just a few pictures’. His eyes got really big as he walked through the front door!
August 13th, 2007 at 10:42 am
Why is it that only women have replied to this one? After my divorce from #1 when I was 32, I tried dating many different groups of women. At that age, you find quite a few divorcees. I can’t tell you how many times one of the ladies cried on my shoulder the whole night-why? “Because my husband screwed me!” Then there was another group of divorcees who were so clearly angry with men, that they spent the entire evening telling me what a louse the guy was, and quite angrily I should mention, so when I asked them why they were so angry, the reply was, “Because my husband screwed me!”
But happy times were on the horizon as I met a divorcee who was neither sad nor mad, so counting my lucky stars, I married her. 29 years later, she is neither sad or mad(that I know of), but she was a client, and that is the subject for another blog. Happy hunting.
August 13th, 2007 at 11:56 am
Merrill, I was a single mom for 17 years and had more fun dates than you can count. One of the funniest was a blind date (don’t we all get stuck with them) and the professional clown said I would know him as he would bring me flowers. Well, he showed up with a red clown nose, a pot of soil and a seed packet for me to plant my own flowers. Let’s just say the date was over before it started! I still laugh when I think about it. Thanks for the walk down memory lane!
August 13th, 2007 at 12:01 pm
I have about 4 insane dates. The best is when I was about 25, living in NY - I went on a date that a friend set up. Why do our friends who supposedly know you set you up on the worst dates? OK - not always - but sometimes - boy do they miss the mark. We went to a lovely restaurant. He ordered Opus 1 - a fave of mine at the time. Opus is a red wine. After the first glass - the waiter poured us another. My date proceeded to pick up his glass, which were apparently wet from his water glass and the wine glass went orbiting into the air - missing the outstretched hand of a passing waiter and up-ending all over a beautifully dressed young girl at the next table - who began to cry with red wine runny down her face and chest and pooling in her coq-au-vin. My date apologized profusely and after a few minutes the girl sopped crying - but they left shortly after. Next - oh yes - next! - He ordered the soup - and it came a tad too hot for him - so he bolted upward with a force that knocked the tray out of that same waiter’s hand and the tray with 4 meals slid forward, hitting the wall - while the waiter tripped and landed completely sprawled and spread-eagled over the table of patrons’ dinners. No criers this time. Ready? Yes - we continued on. He ordered the Veal Florentine - and spent the rest of the meal with spinach on two teeth - and no there was no second date.
August 13th, 2007 at 12:21 pm
My worst date was right after my 16th birthday party. My parents are a bit old-fashioned and had some pretty rigid views of the type of person who would make an appropriate mate for me, and so did many of their friends. For my 16th birthday party, after I had opened my gifts, my parents announced a surprise gift from them. In walked a boy I hardly knew (and didn’t much care for) with a big red bow on his head. My parents had decided to allow me to date by fixing me up with someone they felt was appropriate - the son of one of their friends.
Needless to say, I was horrified and completely embarrassed. To make matters worse, when we went on the date, this boy was the most “handsy” person I’d ever met. My parents never tried to help me decide who to date after that!
August 13th, 2007 at 12:48 pm
This is too good to pass up.
I met a man on the first day of my first job out of college. His office was the next cube over and I really wanted to date him. He was cute, smart, and a snappy dresser. And, he had a ‘policy’ of not dating women from work, so that really clinched it. He was going to be mine. I launched a ruthless campaign of flirting, tossing paperclips over the wall and generally being a pain in the behind. When none of this worked, I told him that I was considering getting a kitten and since he had talked so much about his cat, I was going to come over and see how the cat was working out in an apartment. And, I said I’d bring some steaks and we’d make dinner. He sort of said ‘okay’, but didn’t make a strong commitment. Of course, I assumed we were on.
About an hour later, he poked his head over the cube wall and said that I could come over, but that if I brought anything, he wouldn’t let me in. He was going to make dinner for me. Now, I had him — I thought.
I arrived with a bottle of wine and he still let me in. His apartment was virtually unfurnished except for a telephone cable spool which he used as a table and milk crates which he used as chairs. Other than that, there was a bed, a bunch of free weights, and a plaster doberman. No cat in sight.
I asked about the cat and he went to the balcony, where the plaster doberman was perched, surveying the parking lot, and started to yell “Pork Salad!” at the top of his lungs. After a few yells, a grungy street cat leapt through the sliding door and began to rub against the corner of the kitchen wall, at which point I noticed a really gross grey smudge that went up about three feet. I bent down to pet the cat and it bit me, at which point he admitted it was a stray tomcat that he fed sporadically. Not his cat.
We sat on the crates at the spool table, ate the meal (chicken and eggplant parm — a notable effort), drank the wine and laughed all night. One year later I married him. We’ve been laughing together for 22 years. Neither of our children are named Pork Salad.
August 13th, 2007 at 7:21 pm
My story is also a funny high school story. This happened in Indianapolis, another girl and I had dates and went to a house that had a lot of stories, it was called the House of Blue Lights. We were told that one of the guys had permission to go to the house, why we did not question that we had to climb over a fence to get into the property, I don’t know, but to make a long story short, there was a swimming pool and it had a trapeze that you could swing out over the pool and then drop in. We were having a great time and then all of the sudden we heard a man say, what are you kids doing here and he fired a gun of some kind and said that he was going to call the police. We begged him not to and somehow we got out of there without the police being called.
August 13th, 2007 at 10:34 pm
I went on a first date with a guy in my criminal justice class. It was Christmas time, so he took me to a drive-through Christmas light park that was in the middle of no where. On the way, he started telling me how he liked to put on his mom’s makeup and personal garments. Keep in mind - I was in the middle of no where and had no way to get home (there wasn’t even a phone handy to call for a rescue). I just sat plastered to the passenger’s side door until we got home and I could do a jump and roll technique any air-borne military member would have been proud of.
August 14th, 2007 at 10:34 am
I used to run at an indoor track at the YMCA that overlooked the basketball court where men played pickup games for hours on end. As I ran round and round I spotted a very cute guy and he spotted me as well. He was there every day at the same time I was, and we started waving, and eventually he asked me out for dinner. Now he looked very hot in his basketball shorts, but when he appeared at my door to pick me up he was dressed in an outfit that can only be described as really out of date, and I was way overdressed to say the least. He then told me we had two choices. He didn’t have much cash so we could go to Bonanza (very inexpensive cafeteria style restaurant) or I could pay and we could go somewhere nice. I chose Bonanza where our conversation revolved around his fascination with guns and his subscription to Soldiers of Fortune magazine. It was a very short evening and after that I chose to run the roads rather than on the track. No second date.