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

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

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

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

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

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,

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

“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!



Newsletter sign-up

eLert sign-up

clear sky
45 ° F
48 °
42 °
76 %
1 %
59 °
59 °
55 °
53 °
52 °