Vote For Your Favorite Worst Date Ever Story!
After 9 years as a dating coach, there are times that I’m tempted to say that I’ve heard it all.
But I’ll be the first to admit, I hadn’t heard anything until I asked you to submit your Worst Date Ever story.
After going through hundreds of entries, I’ve concluded that these are the 10 of the worst dates I’ve ever heard about in my life.
Read them all, then vote for the one you think is The Worst. The 3 entries with the most votes will win a year of FOCUS Coaching with me ($554 retail value).
Share it with your friends and vote!
Here are the Top 1o Finalists for Worst Date Ever
I met a younger guy online and was hesitant about meeting in person because he was 23 and I was 10 years older. He convinced me that because he was a native Kodiak Islander from Alaska that he was more mature than the average 23 year old guy. He’d been on that TV show, Deadliest Catch, while on a fishing boat in the Bering Sea, and he had amazing blue eyes, an old soul and great muscles, a young Sly Stallone, so I agreed to meet him. He drove to Maine to meet me (from NH, where he was living) and we met at a restaurant. We clicked so well I invited him back to my house to watch a movie. We ended up kissing and talking all night long. (Nothing more.)
In the morning, I made him pancakes and he asked me for my schedule, saying that he felt like this was really great and wanted to see me again soon! While I was in the bathroom, he robbed me and fled my house so fast, he forgot his pants on the living room futon. I had to call the police, and when the handsome police detective was standing in my kitchen, I pointed to the plastic bag that held the young man’s pants, and told him the whole embarrassing story.
The police officer said, "First, promise me you will never see that young man again." (I thought, yeah, I’ve got that part figured out.) I was concerned that the guy would come back with his friends while I was at work since he’d asked for my work schedule! I never saw him again, though he sent me several apology emails asking me for a second chance. I didn’t give him one. I realized the whole "Deadliest Catch" thing might have been a warning from the start.
After looking through a few stores, he grabbed my hand and asked if I wanted something to eat and drink. We then went to the food court where he told me to order anything I wanted. I ordered a sandwich and soda. I asked him what he was having and he said “half of yours”.
With that said, we proceeded to share our sandwich. At one point he looked over and me and said “meooooow-meoooww” and winked. Not knowing what that meant, I just ignored it. He meowed at me a total of about 5 times during the date. One time I meowed back and then realized how weird this was. I asked him about it and he said he would explain later.
I then told him it was getting late. He said he would walk me to my car. Once at my car he looked at me, said “meow” again and proceeded to nuzzle against my shoulder like a cat would do. He quickly went from shoulder to chest and looked up and purred and proclaimed “Me want to be your kitty. Kitty likes you”.
My answer to this was “Huh? Are you kidding me?”
“Kitty wants head scratched,” he replied.
Against my better judgment, I scratched his head and he said “Kitty wants to go home with you”.
I replied “Okay, kitten, play time is over”. We then said goodbye.
When I got home he left me a voicemail message asking to see me again. I replied via text that I didn’t think we were a good match.
He replied “Is that because you know I’m better looking than you”? I mean, I’m at least an 8 and if you were thinner you would be an 8 too.”
I replied “Yes, that’s the reason”. I then blocked kitten’s phone, text and email.
Hope he found a nice warm home with a clean litter box and lots of treats!
I have my boating license and am quite comfortable around water and boating. It turns out he was a heavy smoker, so in trying to pull the start he starts to cough and grab his chest and thinks he is having a heart attack. False alarm. And since he does not know how to start a boat I start it for him. Myself, him and the large dog of a friend head out. When we are out in the middle of the lake I notice large thunder clouds gathering and ask that we head back immediately. He refuses as he wants to reminisce. As the storm gathers, I become more insistent but he is a very large man and I am a very petite woman and he will not give up the tiller. Finally the storm hits. Here we are in a tiny 9 horsepower tin boat with thunder and lightning all around, high winds, waves coming over our heads, the boat being tossed like flotsam and the dog making it worse by leaping about so the boat nearly flipped with the large dog and large man were on the same side.
I fight for the tiller and inch by inch by inch we crawl back, my heart in my mouth thinking there is no way we can make it. Once back, it is pitch dark. We get to the cabin where I am shaking with cold. There is no fire and he has no food, only 1 beer in the fridge which he proceeds to drink. The power goes out so no light either. He thinks sex might help the equation! However, I run out sliding and slipping through rivulets of mud in the teeming rain to find my car.
Keep in mind that its August – hot and humid – I open the first box and in it is leather opera gloves. I say "why are you giving these to me?" He asks that I put them on. I said "No, I think not" I could guess the next box is some sort of boots!! Of course, I was right. He tells me that the 3rd gift is a gift he bought his last girlfriend and he didn’t get a chance to give it to her. It might be a bit too big for me but he was sure it would be okay. Since I didn’t want any thing more to do with this, he opened it for me. It was a pleather jump suit with no butt in it!!!! I stood up and said he had stepped way over the line. He tried to explain that he had a leather fetish and that if I cared for him I would want to understand. etc. I said "Please don’t call me again." and left. Did he try and call me!!? Yes. Begging I go out with him again. Unreal.
I had been in contact with Bobby, a personal trainer that worked for a reputable gym in my town numerous times via phone calls and texts and was looking forward to finally meeting up for a drink and light dinner.
First thing that went wrong happened as soon as we got to the pub. They were checking ID’s at the door and wouldn’t you know, Bobby “forgot” his wallet. Okay, fine. No big deal, I have no problem paying for a date. So drinks and appetizers were great and we left the bar.
Next we stop by his Mom’s house. Yes, he still lived there, and yes, he gets money from her. Hmm. We leave and he tells me that we are going to meet up with a few of his friends to hang out. So we go over his friend’s house for a bit and I’m sitting on the sofa, having a beer, when out of nowhere I see his friend hand him something. It turns out, it was a crack pipe! Bobby proceeded to smoke crack in the next room for the next hour while I freaked the hell out trying to figure out how to get out of this situation. I began to mention that it was getting late, but I didn’t want to leave until I was sure he was no longer high. I stayed calm and eventually we left.
On the way back to my place, he asked to “borrow” $100 until the following week. I declined, of course. He attempted to kiss me goodnight, but I turned so he got my cheek and I almost ran into the house.
Funny thing is that he called the next night and asked if I wanted to come over and watch a movie. Are you serious? So I went into a rant about how surreal the whole previous night was and all he said was, “Yeah I guess that wasn’t too cool for a first date, huh?”
A nice Jewish man with a few million decides to take me for champagne tea at an old large estate turned hotel with gorgeous gardens. During the drive, he told me about at least 3 women he had recently been with, about their personalities, what he liked and didn’t like about them, how good they were in bed, and if he was interested in them.
He continued bragging about his two boats, his house on the Thames in Berkshire, England, how he didn’t go to school and became a high paying consultant. All of a sudden he said to me, "I look successful but in truth, all of the money to buy the house, boats, and holidays abroad are from my wife’s inheritance.” He then showed me pictures of this gorgeous English woman with blonde hair and long legs. I asked him, “What are you doing here with me when you have such a beautiful wife at home?”
After laying the whopper on me that he was married, I felt very uncomfortable do I get up and go or stay and find out more.
He then said to me, "I will pay you to have sex with me." I got up looked around and threw my hot Earl Grey in his lap before saying very loudly that I am not that type of woman. I turned around and walked out. Many months later, he is still trying to call me to find out what went wrong!
He was just the way I like them, tall, lanky, really good looking and confidence oozing out of every pore. Later he came up for a chat; he was witty, intelligent and charming as hell. I knew I would fall for him hard and so gently declined him when he asked me out repeatedly for a coffee or lunch after classes. After about a month, he called me on a Saturday afternoon asking if I would like to go for a rock concert in the evening. I had fallen for him in spite of myself and wanted to take a chance hoping that this might be it, and said yes. I picked him up since he didn’t own a car.
The evening turned out to be great, we had a couple of beers and cheered for the bands plus he made me laugh all the time. Later while we were leaving, we ran into another art class member. She was in the same under grad course as him, was very drunk at the time and had supposedly broken up with her boyfriend moments ago that same evening. She decided to join us and we let her since she was upset. She wanted to drink some more, so we bought more beer and had it while sitting in my car in the parking lot while we chatted. I was in the driver’s seat, while my date sat in the passenger seat and this girl was in the seat right behind him. He held my hand in his and while we sat there laughing at his funny stories, this girl started feeling him up from behind. Her hands were out of control and were all over his neck, and chest. He repeatedly asked her to keep her hands to herself and shoved her away but she came back every time.
This was a bit too much for me but I didn’t say anything, for she was his friend and was very drunk. After a while, I excused myself to go to the washroom and came back to find his seat pushed back and his head between her legs. Imagine my state of mind as I sat through the last twenty minutes of the show. I couldn’t have walked off since the car belonged to me, and I am just too nice to throw drunken people out on the street in an unknown area. I dropped them off at their respective dorms and went home.
The plan was to meet at Mr. Date’s downtown high-rise to watch the sunset and then dinner at Brasserie du Vin, my favorite restaurant and only 3 blocks away.
I savored the magnificent view of the city as the sun set. Mr. Date joined me on the balcony for a moment then started wandering around his apartment yammering on out of hearing range. Was he angry? He admitted to being so nervous that he had to either take a Valium or smoke some pot. I requested he not smoke pot as I don’t want second-hand smoke. He took the Valium, and then pronounced I was just what he was looking for. I guess he assumed I would feel the same and want to spend the night with him because he hung his head and admitted, “I haven’t had sex in 6 years! I don’t even know if I could do it.” I assured him that only having known him less than an hour, I would not make any demands in that regard.
On the brief walk to dinner we stopped at a flower shop as he wanted to buy me a lei. I picked out the most yummy, fragrant white ginger lei! I asked him to take a picture of me wearing it. He steadied his arm on a wire shelf to take the photo. The shelf turned out NOT to be a shelf after all, but a large gray cage holding a large gray parrot that quickly chased away the intruding arm with a silent nip. The parrot’s aim was impeccable. He nicked the ropy vein on Mr. Date’s inside forearm and caused quite a gush of blood. The flower girl offered a Band-Aid but my friend called for antibiotics and a tetanus shot. I reassured him with a single chilly glance that he would be fine. Bleeding staunched, we continued our walk and made it to the restaurant without further incident.
The table was in the courtyard blooming with stephanotis vines and lush planters of succulents and tropicals. The food was divine, the waiter cute, the wine welcome. The conversation, however, left much to be desired. The cathartic effect of the Valium and wine loosened my date’s wrinkled lips and he talked non-stop about himself throughout the meal. Some of what he said was interesting. I would have loved to join in, but Mr. “Windbag” kept cutting me off whenever I tried to say something. He was very complimentary though– my beauty, intelligence and well-written profile set me apart from all the others and I was just what he was looking for. He REALLY wanted me…….
And he DID want me: he wanted me to pick him up from his colonoscopy on Friday! I demurred, he persisted, I resisted. He laid on the guilt. “So you expect me to just take a taxi in that condition and be alone all night?” I stood my ground. “Mr. Date, I have only known you three hours. I need time to get to know someone before I’m comfortable with that level of intimacy.” He acquiesced. We left the restaurant and he walked me to my car.
I gave him a hug goodbye. He was not receptive to it and stiffened.
The next day Mr. Date called me, as any gentleman does after a good date. Instead of thanking me for the nice evening, he apologized for being unresponsive when I hugged him, saying, “You see, I have gas and was afraid that you could smell it when you hugged me. That is why I’m having the colonoscopy and I need you to pick me up!” He asked me to come over to watch a movie and go for a swim. I declined.
I have been taking Evan’s advice and being more open to men based on compatibility rather than age, looks, height or body type. But I’m going to think twice about going out with an old fart again.
His real age was 34, mine is 48. He put 49 as his age on the site. The picture he posted was altered. He admits all this upon meeting and explains he’s only attracted to older women. He wanted a drink before dinner, he had a couple of martinis, I had a glass of wine. We moved on to dinner. Two more martinis for him, water for me.
Conversation traveled when I asked him why he’s interested in older women – answer: it goes back to adolescence – he was a peeping Tom – looking into the windows of friend’s houses with hot moms – did it for years and still has the urge sometimes. I steer the conversation back to not so intimate topics. He begins to eat his food with his fingers sucking things into his mouth slowly. I’m waiting for something to happen – a noodle slap to his nose – something – all the while he stares at me intensely. Sucking noises escape from his young, barely lined face as he eats. I request that he use his utensils. He complies winking at me knowingly.
We wrap up dinner and I’m relieved to head home. He walks me to my car, and gropes my rear. Grope isn’t accurate: he probed, he squeezed my butt, he touched my crotch with fingers that wiggled and explored. I jumped back, shocked. He apologized and blamed the alcohol and my age. If only I were younger. he wouldn’t feel tempted this way. We get to my car and he asks me to wait there, he wants to pay my parking and he’ll be right back after he gets his car.
He reappears driving an upscale red sports car with the personalized front plate “Shagadelic.” He pulls up and tells me he has a present for me and that I have to accept it. He says it’s an apology for grabbing me. He hands me a gift-wrapped box. I reluctantly take it through my car window. He’s happy I’ve taken the box. He leaves and pays my parking. I’m home. I don’t open the box. Phone rings. Mr. Shagadelic wants to make sure I got home alright. “Did you open the present?” he asks.
I go and get the box and open it. It’s an 8 inch purple dildo with a package of batteries. He says in a low voice “I want you to know I’d never give anyone something that is bigger then me.” I kindly tell him to lose my number because he’s just too much of a bad boy for me. As I’m hanging up the phone I hear his voice “Yes, I’m a bad boy, a very bad—“
This was my first date after 17 years of marriage and 2 years divorced.
We met online – shocking! And we spoke on the phone 1 or 2 times before we met. Now one of the recurring themes was that he was a superb athlete and that he played cricket almost at a professional level and that he played squash very competitively and that he played every day. Now I didn’t think too much of this, though I was a bit annoyed at the fact that he mentioned it that much. But I liked him well enough to set up a lunch date with him.
There I was waiting for him, when I saw him walking towards me in the street. He was limping a lot – it looked rather painful. Now of course he had played squash that morning because he’s a squash ‘pro’, so I say ‘wow, looks like you got hurt playing squash today. What happened?’. Now I forget lots of things, but I can’t forget that he looked me at me so perplexed as if he had no idea what I was talking about. I just dropped it – it looked like maybe he had a disability – so now here I am thinking ‘wow insulting the disabled is always the way to start a date."
We head down the block to the restaurant. He has more than a limp. I am no medical expert, but it looks like maybe he had a stroke and has trouble with the right side of his body. Not that big a deal, but really there is no way this man is throwing himself around a squash court on a daily basis.
He proceeds to order a steak – this is just painful to watch because he cannot grasp the cutlery well enough to hold down the steak and cut it at the same time. I am being cook, talking, being lively, sharing about me, trying hard to earn that Oscar and pretend that hey nothing is wrong here.
Halfway through lunch, he falls out of his chair and is sprawled out on the floor of the restaurant. This is the point at which I am regretting that he suggested a nice place. Now the chairs were wooden (funny what you remember) so when his chair crashed in one direction and he tumbled in the other, it was loud. So loud indeed! I wanted to die. People were staring and one man jumped up and ran over to my date to help pick him up off the floor.
Once he was back at the table and I ask ‘Are you okay?’, he says ‘I am fine but the ego is a bit bruised.’
Remember, you only get ONE vote, so choose carefully.
Make sure you vote before midnight Sunday May 13th, and then share this with your friends so they can get a good laugh!
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Let me know what you think about the stories below!