Worst Date Ever 

Readers' tales of dating woe.

He Was a She

My worst date was when I discovered he was a trannie. Um, actually happened twice.

That's all the details for you.


No Cerveza Por Favor

His preferred cuisine was Japanese. Mine was Mexican. It was our second date. We chose Juan's Place, at Ninth and Carleton. I was a senior studying electrical engineering at UC Berkeley. Bill was a grad student in the same department. Beset with nervousness, he quickly downed two bottles of Pacifico, followed with a fine Mexican meal. To my surprise, this sequence of events created with physicists call a Rayleigh-Taylor instability: infalling mass on top of meandering bubbles. As we departed, my date rapidly vomited over the curb outside, just across from the animal shelter. (Picking up or delivering?) I scooped him up and draped him across the back seat of his vintage brown '67 VW bus and drove him home. That was 1979. We are happily married. Our teenage son and daughter prefer Japanese food to Mexican. We still dine at Juan's Place occasionally, but the meal comes before the beer. Bill hasn't lost his lunch in such a romantic manner since. And never since that night has he consented to letting me drive his car while he is passed out in the back.

Amelia S. Marshall, Oakland

Appetite for Destruction

My first date with Gab was one out of a fairy tale. We had a picnic in Dolores Park. He brought wine and cheese and when he took out the 97 percent dark chocolate for dessert, I almost came in my pants. After a few glasses of wine, we decided it was a smart idea to go back to my place. He was such a gentleman. When I jerked him off, he even came in a napkin! He left soon after and we agreed to see each other the next weekend. He was going to take me to dinner!Once Saturday came around, I was super pumped for our date. I hadn't eaten anything but vegetables and gum for almost a week, so needless to say, I was looking good. We met at the bar, had a glass of wine, and flirted until our table was ready. Once we sat down, Gab took the liberty of ordering for me. I started with a goat cheese and beet salad, which I immediately spilled all over myself.I was so embarrassed. I apologized profusely and prayed that being a klutz was a major characteristic that he looked for in a woman. Turns out it was. He told me that he was in fact thrilled that I spilled all over myself. He went on to explain that he has a lot of anxiety around eating in public and the fact that I eat like a seven-year-old made him feel at ease. Aww, he's sensitive.  I ate what was left of my salad and then it was on to the main course. I gingerly started eating my five-star meal, but realized that Gab had not touched his at all. I asked him if everything was okay and if he needed me to spill some more before he could eat. He then took a big gulp of wine, looked me in the eyes, and said, "I'm anorexic." I of course thought he was kidding, because everyone knows that manorexics are an urban legend.  But he then described in detail all the issues he had with his family. We are talking deep-rooted stuff that you shouldn't share with anyone until they have a ring on their finger or you are paying them to listen.The rest of dinner dragged on. I of course could not eat my halibut because I felt guilty for eating. So we both sat there pushing our food around and talking about his father's control issues, his sisters' inability to connect with anyone, and his crazy mother. All of which apparently lead him to not eat and to as he described it "self medicate."  It was worse than watching Dr. Phil. Finally, the bill came and I was so excited to go home and eat everything in my fridge.Gab told me he had a great time and asked if I wanted to go back to his place. I declined, insisting that I had early morning plans. He shrugged then gave me a hug and before he pulled away, he leaned in and whispered into my ear, "There is one thing I do eat."


Did She Really Say That?

There may be a tendency for a writer to embellish a "worst date ever" story for gluttonous entertainment. But this tale is achingly true. An Internet date that made me question my very life purpose.

We exchanged the token frivolous Match.com e-mails and decided to meet at the Rooz Cafe in Oakland next to the Parkway Theatre. It would be a cup of coffee and a movie. The length of this date idea is just simply wrong for a first encounter. But, there I was sitting in Rooz on a cold winter night. In she walks, and waves manically, as she crashes toward me. She looked a lot older, unhealthier, and beaten up by life than her work, as a Feng Shui interior designer, would have led me to fantasize. Even though it was near freezing outside, she immediately took off her jacket to reveal a child's size tank top. She looked down at her tattooed arms, and back up at me, with a devilish twinkle, and cackled, "If you are a good boy, I will show you some tattoos later that are in hidden places." I laughed nervously. Did she really just say that?

A few minutes later she made a fatal error. In the midst of some incoherent sentence she mumbled, "So if we get married someday ..." I didn't hear the rest of her flirtatious babbling. I internally pondered that if there was a guidebook for what to never say to a man, especially on the first date, she had not read it.

At this time in my life, I was getting my master's in psychology and was becoming a psychotherapist. As I sat across from her, I could not help but internally diagnosis her personality disorder, but, I tried to remain calm and interested. Hell, I had a drama minor in college. I swatted away her flirtatious statements gracefully, in my opinion, but as I was gazing over at the musician playing the harp in the corner of the cafe, I was immediately jolted back into my unfortunate reality. My date violently blurted out, "Do you want me to leave?" I was shocked. I calmly told her that I was just noticing the musician. She seethed and reminded me that I was on a date with her. With fear, I glanced down at my watch and suggested that we go to the movie theater. It gets much worse.

As we walk in silence toward the theater, I notice that I am starting to feel sick. I feel a sore throat coming on and I am feeling vulnerable to the cold outside. I start to shake. I look to my left and see her scowl and know that there is no comfort to be had by her. As we buy tickets, we are told that the heating system in the Parkway is broken and that they have blankets if we are too cold. Here I am shaking and feeling sick and we are heading into a meat locker. As we made our way to the couch, I notice that I can see my breath. I sit on one end of the couch, arms crossed and shivering. She looks at me and deadpans, "You are sitting so far away, why don't you just sit on another coach." Somehow she is missing my "I don't want to cuddle" cues. Again, I nervously laugh and pray for the previews.

I glance around at the other fortunate souls on dates and turn to see my ex-girlfriend's best friend a couple of seats behind us. Let's just say that my ex and me did not end on a good note. Her best friend would most likely tag team with my date and say unkind things to me if I was spotted. I quickly turned toward the backs of heads in front of me and slid myself down on the couch in a fetal-type position. My date was talking to everyone around us, as an obvious defense to my abandonment of her. I could tell that her mania annoyed others too.

Toward the end of the movie, (which sucked by the way), I realized that I was in a triple bind. One, I am feeling colder and sicker by the minute; Two, I need to find a way to avoid contact with my ex's friend; And, three, I have to go to the bathroom so badly that I ache. Not to mention that I have an angry tattooed woman in a tank top sitting next to me.

As the ending credits begin to roll, I tell my date that I need to run to the bathroom. She rolls her eyes at me and tells me that she is going to talk with her new friends (who, by the way, look at me pleadingly to take this woman away). I run past my ex's best friend without her noticing me and get to the bathroom. Apparently the movie in the other theater got out minutes earlier and there is a long line out of the men's bathroom. What is this, a Coldplay concert? I stand and shake from side to side, to keep me warm and to avoid peeing in my pants. I look to my right, and as if in slow motion, I see my ex's best friend walking down the stairs towards me. She has not seen me yet, so I do the unexpected. I run. I literally run out of the theater to my apartment, which is a block away.

After I relieved myself, I text messaged my date and told her that I was home. I turned on the heater, crawled into my warm bed, and thanked the heavens that I got out of my date without any bruises. The next morning, I saw an e-mail in my inbox that I knew could not be too good. It was a 10,000-word e-mail from my date. She told me, in a number of creative ways, how horrible I am going to be as a therapist, because I obviously had no heart, and no humanity. I read her words and literally doubted my new career path for a moment. Was leaving her at the theater so heartless? Does a choice like this reflect my ineptness as a therapist?

No. To this day, I do not regret my decision to run, for SO many reasons. But mostly, I avoided the prospect of seeing the rest of her tattoos against my will. Yes, she was that scary.

Paul Ginocchio, Oakland

A Painful Experience

Worst date ever? Is that for me, or for the woman?

The worst date ever, for a woman I dated, was our first meeting, which was a paddle, in my tandem kayak, to Angel Island for lunch.

Lots of things went wrong, at least from her point of view. But the biggest mistake I made was the choice or route — around Angel Island. The paddle took five hours, and in returning to Sausalito, we had a big headwind and were also fighting an ebbing current.

She was late for an important meeting, which was upsetting, but also apparently hurt her shoulder as well, from the effort. Last time I contacted her she was going for an MRI, with possible surgery to be scheduled.

Yeah, any date that ends with a visit to hospital, especially a first date, has to be on the list of worst dates ever.

P.S. I had a good time, and actually wanted to see her again, but, I blew it.

Danny Forer, San Rafael

Desperately Seeking Sanity

In the fall of 2003, I found myself standing in line dressed in a stylish business suit with hundreds of other job seekers at an employment fair held at the Centennial Hall in Hayward. I was handing out my résumé left and right. I approached a medical resource booth operated by an attractive man. I inquired into a particular position. He said, "I am watching the booth while the boss is on break."

I said, "Did they hire you just to hang around and look good? Or can you give me information?" He smiled. I chatted about recently moving to the East Bay and handed him my résumé. We joked about a dinner and a movie. I moved on in search of employment.

A day later, I received a telephone call from a stranger. It was the man from the booth. He wanted to know if I was available for a date on the weekend. Puzzled, I asked him how he knew my home telephone number. He said he had copied it off my résumé. I thought nothing of it at the time and agreed to a date with him. We decided to meet at Centennial Hall.

As he exited his car, he was limping with a cane. His clothes were a little shabby. I offered to drive us to the Old Spaghetti Factory at Jack London Square. He seemed pleasant at first. At the restaurant, he said how flattered he was that I had complimented him. As we sat down to begin our meals, the madness began.

He began by asking me what is my religion. With my salad in front of me, I replied that I was Roman Catholic. He informed me that I should know that the Pope is an agent of the devil. That it was well documented that the Roman Catholic was created by Satan as a way to spread his evil deeds throughout the world. Since I am curious by nature and I was famished, I decided to see where this strange date would take me.

I changed the subject to my discovery of the scene at the University of Berkeley. I told him it was wonderful to find street artist and vendors. The people were very interesting. I inquired if he had ever had a tarot reading on Telegraph Avenue. With a look of horror on his face, he said by participating in tarot and reading astrology I was damning my soul to the hell fires forever. I suppressed by laughter as the waitress brought the entrées.

In between bites of pasta, I decided to change the subject to family. I told him I am a mother of a young child. I had two years prior ended a fifteen-year relationship and marriage. I asked him if he ever had been in a long-term commitment. He replied that he was divorced and he had four children. He sputtered that he had received custody of his eldest son and his ex-wife had the three children. When I inquired into their ages, he informed me that he had not seen his three younger children. Surprised, I asked why. The witch, his ex-wife, had obtained a restraining order against him. She had taken their children and returned to Europe. He had no way to contact his kids except through his ex-in-laws whom he badgered to get information. I began to worry as to why a woman would need to get a restraining order against this man.

I searched for the waitress and asked for the check. As we waited for the bill to arrive, I changed the subject to employment. How did he like working for medical company? I asked. He said he was doing a favor for a friend and did not work for the company. He was on disability and recording at a hospital. In turn, he began to quiz me regarding my employment history. Why had I switched from teaching to nursing? How had I liked attending university? Why had I taken time off from work? I searched my mind as to how this man would know so much about my education and work history. Then, it hit me.

He had memorized my résumé. The feeling of nausea spread throughout my stomach with the realization that this strange weird man was privy to the last fifteen years of my life. As he paid for the meal, he informed me that this meal had been expensive for him. We would no longer be going to the movies. He said, "The next date can be at your place. I prefer to stay in and watch a video." Oh.

As we walked to the car through Jack London Square, I thought about ditching him. He could hail a taxi to Hayward. I was tired of his strangeness. Then, I remembered he had my home address. I drove us to Centennial Hall.

Along the way, he informed me of the numerous peculiar ideas floating through his head. Had I seen Texas Chain Saw Massacre? No. Did I know it was a true story? No. On and on, he continued telling me of his beliefs. Finally, we reached our destination. As he stepped out of the car, I explained I needed to leave and raced away from his car.

Now, in 2009, I am happily committed to my loving family. I can look back at that crazy date as one of the strangest and worst dates in my short dating life.

Nancy Mah

Cows and Courting

About four years ago, I was working as the day manager at a bar in a small town in Minnesota where there were weekly cattle sales. This guy, a rancher from South Dakota, would come in every week after the cattle sales and hang out at the bar. One day, he came in early before the sale and ordered a lemonade. I thought it was a little weird but didn't think much of it. He stared at the bar for a good two hours and finally, without looking up, asked me out to dinner the following week. He was so shy and nervous that I felt I couldn't say no. Plus, he seemed like a nice normal guy.

It was the first real "date" I had ever been on, so I was a little excited. I put on a dress and heels and got all pretty. We decided to meet at the other restaurant in town. He showed up in his cowboy best: Stetson, large belt buckle, new dark Wrangler jeans. But he was really shy, so I did most of the talking. I asked him what he liked to do for fun. He said he basically just works on his ranch with the cows. He didn't like to read, watch movies, watch TV, or do anything besides work with his cows. He said he golfed once the prior year. Then he started telling me about his ranch in South Dakota: how big it was, how he was doing really well, etc. All he needed next in his life, he said, was a wife and babies. This was after about 45 minutes of talking. Needless to say, there were a lot of moments of awkward silence after that. I couldn't believe he was already talking about babies! I couldn't imagine myself in a town smaller than where I lived, thumbing through catalogs and ordering furniture amidst herds of cattle. Not the life for me. After dinner, he asked me if I wanted to go across the street to the bar at his hotel, where some of his rancher friends were. I thought if he started drinking he might loosen up. So I agreed. We got there and he and all his rancher friends sat around talked about — you guessed it — cattle. I got bored so I watched Monday Night Football. At the end of the game, I exclaimed to no one in particular, "Yes! All my football picks were great!" "Pigs?" asked one of the ranchers next to me, excitedly. "Did you say 'pigs?' Are they for sale?" "No!" I blurted back. "Picks! As in, football?" I replied. Clearly, these guys thought about nothing else but livestock. My date then leaned over and asked me, "You don't seem to know very much about cattle, do you." "Um, no, I don't," I said. "We should go see the cattle barn, right now," he said. "Now?" I asked. This was at midnight, mind you. I turned him down several times, but finally agreed to go check it out. We drove to the cattle sale barn in my car. I was hoping to just leave him there. The smell of the place was awful — there were about 55,000 cattle there. We walked over the cows on this metal grate called the "catwalk." I tottered in my heels, trying not to fall through. He led me around, showing me all the different types of cattle. "That there is a 700-pound heifer," he said, pointing to one of the cows in the dark. "Oh, wow," I said, trying to feign enthusiasm. We got to the end of the "catwalk" under the moonlight as thousands of cattle milled about underneath us and I thought this was his moment to try and lay one on me. Sensing this, I quickly turned around. "Well, I'm pretty tired," I said. "We should probably head back." We walked back to my car and I drove him to his hotel. Before he got out, he leaned over to give me a good-night kiss. I closed my eyes and mouth, hoping it'd be as harmless and least intrusive as possible. Not only did he try to pry my mouth open with his tongue, but he then proceeded to LICK MY ENTIRE FACE — big, long licks over my eyes, my cheeks, the whole thing. My face was completely wet. I think my look of horror prompted him to finally stop. I thought that'd be the end of it, but no. The next week, he sent me flowers at my work. I told him that he was nice but I just wanted to remain friends and that I didn't think we had a romantic connection. He seemed a little bummed, but clearly didn't get the message. The next week, he came in with a ticket for two for a Caribbean cruise. Again, I had to let him down gently. He was a nice guy, but I just couldn't see myself as a cattle-rancher's wife. Plus the whole licking incident made me wonder just how close he had gotten to his cows.


Vacation from Hell

It was 1961 — I was 21 and quite naive — I was in Puerto Rico on vacation and met a very big, handsome Puerto Rican man who took me to his job site at a hotel. While we were in his cabin, he tried to rape me. I screamed and miraculously the house detective just happened to be walking through that isolated area at that moment with all the keys.

In 1961 people weren't known for carrying knives and guns. Thank goodness I will never forget that!!

Anne, Oakland

A Date at Church

My worst date was when I met a man from ad of your newpaper about this dating service located San Rafeal city area They printed my name and phone number And I got a call from a man I told him I cant find a sitter for my son He said fine no problem. He took me and my son to our neighborhood fast food restaurant church fried chicken, we talk little ate drunk and 45 minutes later my son said he wanted to go home. As me and son walked the man to the West Oakland Bart Station he all of the suddenly sput out "my God man this date have been a diseaster. You bought your son along. We ate drank and I've spend 45 minutes with you" As he went on and on I had a tight scare smile on my face. He look at his watch and said "Yeah only 45 with you." As he was about to go to the Bart Station he said to me "Sold thank you for taking you out" "Thank you and I really had a nice time" I said then added He walked away with a disgusted look on his and as I walked home I said to my son "I don't do this again. I seem to meet losers, jerks" then the next 2nd man that called me and my son had 1 year of wonderful time with him then he dump me Now I got a next door neigbor male friend who use to be close to me and me and son are happy that way


Hint of Mint

It was my junior year at Michigan State University, my dorm mate Ostrowski approached me and said, "how wouldja like to go out with a Philly from Philly on a double date with me and my honey?" As he said this he pulled out of his wallet a picture of his girl Michelle who was standing with her girlfriend Vanessa from Philly. "There she is Doug ... ya just can't say no to this one ... I mean Michelle told me she's into artistic types ... you know those assthethes" ha! ha! he chortled at his own pun. As I scanned the photograph I could see she had marvellous auburn hair and beautiful blue eyes that looked like a tranquil sky without any clouds ... eternal translucent blue which stirred my artistic senses not to mention my gonads. The spittin image of Grace Kelly ... she was. I couldn't say no. I was ready to head out the door and go anywhere with Ostrowski and his girl so long as Vanessa was there.

We agreed to meet the girls at a fancy Italian restaurant off campus called La Cenerentola and like Cinderella I felt the night of the big ball had come. I was nervous with anticipation and I started popping one green Cert in my mouth after another. I told Ostrowski I had better go to the bathroom one more time and also check out my suit and tie to see that I looked okay. Ostrowski thought that was a good idea too. After I did my thing I went over to check myself in the mirror. I looked straight on, left and right, saw that my hair was in place, etc.

Everything looked fine and then I smiled to check out my pearly whites.

"Oh shit, Ostrowski, look at this!" My whole mouth, tongue, and teeth were solid green! I looked like an Irish Chow. "Say that's cool Doug ... I am going to call you Danny boy —you look like a leprechaun turned inside out ... ha! ha! "What am I going to do?" Order the Halibut Florentine — it's got lots of spinach in it-maybe it will cover it up-ho!

ho! I tried rinsing my mouth out, but it didn't help. "What am I going to do, Ostrowski?" "Keep your mouth shut as much as possible. I'll take care of the rest."

We went out to meet the girls and I didn't say boo! Ostrowski introduced me to Vanessa and I just spoke with clinched teeth. "Nice to meet you." Ostrowski told her I had recently had some wisdom teeth removed and couldn't talk too much. She bought into it and we nodded yes and no most of the evening. Finally, the evening was over and we parted ways.

Never again did I use those green pellets — I made sure they were the white mints that don't leave a stain!

Doug Burgess, El Cerrito

The Worst Non-Date

In my senior year of college, I had been dating this one girl for a few months before Valentine's Day, but things were a little rocky. I had planned this nice Valentine's Day dinner in Berkeley and was looking forward to it. Whaddya know, she ended up breaking it off the day before — February 13. On the morning of Valentine's Day I was milling about the house, doing yardwork and such, and while adjusting our finnicky sliding-glass door, I managed to drop it square on my big toe — with bare feet. It was extremely painful, to say the least. Trying to keep my mind off my recent breakup and increasingly swollen toe, I adjusted my date plans for the evening. In the end, I went out to Cold Stone Creamery with a male roommate after spending dinner at home alone, then tagged along with a few other singles to a French indie flick about incest or something, barely able to concentrate due to the pain in my toe. I ended up losing the nail and never patching things up with the ex. My most memorable Valentine's Day ever, without a doubt.


No Happy Endings

This was the third date with a girl from college. She told she wanted to take me out on my birthday, and give me a special day! Boy was I excited, she even said she was going to pick me up from my house, and that we were only going to do things she knew I liked.How could this go wrong? I was gonna get to see a cool band and at least get a BJ for sure. Wrong! She picked me up from my house and took me to lunch, and slid me the check ... and then took me to a movie (I hate the movies ...) and then ... hip bumped me closer to the box office teller ... to pay.I suppose the real deal breaker was when after the movie — I asked for a BJ, she ... "doesn't do that," she said. Needless to say it was a tacky evening with zero BJs for me. Side note: I don't care who pays ... But every one in the whole world should get a BJ on their birthdays.

Ryan, Livermore

Who's the Jerk?

It was my first online dating experience where I actually met up with the guy that I had been talking to for over a month. He was great on paper — attractive, outgoing, cool profession, adventurous, the works. We got along great in our conversations online, so we thought it would be a great idea to meet up and see if it worked. We met at a bar where ten of my best guy friends just happened to be there, with no ladies attached. I got there first, got a beer, sat down to wait for my date, and didn't realize that my friends were there. When my date arrived I knew instantly that this wasn't going to work out. All of the sudden, the guy on paper turned into a completely different person. Turns out he didn't voluntarily leave his job, he was fired. He was shorter and more stout than he projected in his profile, and it was as though the biography I had once read was turning into a tall tale.  I knew I had made a mistake. Everything was fine and I was pushing through it, until my group of ten guy friends came over to where we were sitting and the poor guy was completely pushed out of the conversation and table. None of my friends knew that I was on a date, and I wasn't making any effort to seek a more private venue for us to talk, so things became progressively awkward. My guy friends are aggressive, flirtatious, and have dirty minds and senses of humor to go along with it. At one point, one of my friends picked me up, swung me around and then planted one on my lips just to mess with me because he thought it was funny. Another decided that he was going to tell every stranger he met (including my date) that he sold crack ... and he never broke character. I was becoming increasingly embarrassed as it appeared this guy wasn't getting the sort of sense of humor my friends provide, and I just wanted to get out of the situation. He suggested that maybe it was time to go home and end the evening, and I quickly agreed. I didn't even say goodbye to my friends, headed right out the door and out onto the street. We walked up the street a bit, and he offered me a ride home ... which always means a chance to make out in the car ... so I quickly declined and told him that I would just grab a cab, no big deal, he lived close to the bar, don't want to trouble him. I gave him a hug, and yelled out, "we should do this again sometime!" as I ducked into the nearest cab and quickly shut the door. I watched him walk up the street, toward his house, away from the bar, turned to the cab driver and said, "I just need to go down to the end of the block." I paid the cab driver $5 to drive me one block at which point I hopped out, ran back into the bar and continued to party with my friends until last call. So I guess I'm the evil person here, but it was excruciating to stick around with the guy any longer than necessary. Watch out for online dating!



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