My Very Worst Date was a string of two dates. Safe to say, I don’t learn my lesson easily.

The guy was someone I met online. He was very persistent in his attempt to get me to go on a date with him, despite my better judgement. Nothing about him matched any of the things that I was looking for in a partner and had written about openly on my profile. He had toured with the Grateful Dead for a few years and somehow thought the fact that I had dreads made us the ultimate match. Anyways, back to business.

Our first date was to a Grateful Dead hole in the wall bar about two hours north of where we lived. I’m not much of a drinker and was totally out of my element. I quickly learned that he was quite the drinker and felt right at home, even asking a random lady if we could “crash” at her place that night. Instead, he decided it was good judgment to take his open container with him in the truck and drive back home. Not the worst date ever, but I should have learned my lesson.

The second date was to a restaurant downtown that happened to be my favorite place to eat. We were sitting there and he was smirking at me. He then commented that I wasn’t anything special and that he wasn’t sure why he was there with me. I got up to use the restroom and compose myself and when I came back, he was gone. As in, I had no ride home, was five miles from my house, in new sandals that had worn a blister on my foot, and with a cell phone that was almost dead.

I called a friend and got a ride home only to receive a text from my date about half an hour later asking if he could give me a ride home. He proceeded to harass me for the next few weeks, even bringing over a bicycle one night that he had found at a garage sale.

He sent me a message on Facebook over a year and a half later, telling me that he had “finished himself off” to the image of me four times in one day. Safe to say, I blocked him.

I met this guy through a dating site and in his profile it said he was 35 (at the time I was 25).  I had just moved to the city and was excited to meet people.  He was from Australia and he looked very attractive in his photos.  We emailed each other for about a week before deciding to meet up.  He worked in fashion and it was a busy time for them so we just decided on coffee.

He told me to meet him in front of his job. As I walked up I saw a guy there.  He looked vaguely familiar.  I thought this cannot be him.  This guy had a head FULL of grey hair; the guy online had dark hair.  Ok, whatever, it’s distinguished like Anderson Cooper.  I got closer and, wow, this guy was ABSOLUTELY NOT 35.  His profile photos were at least ten years old if they were a day.  He saw me and smiled -  I then had a flashback and noticed something else: he was not smiling in any of his photos and now I knew why.  Eek.  I thought to myself, well, it’s just coffee and he may be a great guy.  This is  a new me and I’m not going to be shallow about this.

So we got coffee and were having pretty great conversation.  I was thinking, I can look past this, I really can.  Then he reached over, took my hand, and started talking about marriage.  Huh?  He wasn’t specifically talking marriage to me, just marriage in general – but on a first date it’s still a weird subject.  I wanted to get up and leave but, damn my good manners, I stayed.  Thank goodness this was only coffee and he was on a break from work, which he had to get back to.

We talked a few more times on the phone; he still kept bringing up marriage and trying to get me to come to his house.  It slowly started to dawn on me that he probably needed a green card.

I met T on an online dating site where I had previously met a boyfriend and several platonic friends. I live in a big city but don’t have a car. At the time, I relied solely on public transportation. T lived in a totally different city, about 20 miles away. However, he attended the university that was just a few blocks from my apartment, so we agreed to meet there for lunch. The fact that he didn’t offer to pick me up and drive me somewhere was OK, since there was a strip mall type place on campus, and I figured we could get Chinese food or something.

I didn’t know where anything was on the campus, so I wandered around for a while until I found T. And he did not look like his pictures. He was still moderately good looking, though, so I figured I’d continue.

Instead of walking to where the restaurants all were, we went to the student lounge. Which would be OK, except I wasn’t a student there, and the only food place was Subway. I like Subway as much as the next person (except maybe Jared), but not for a first date. But what’s even worse is that he didn’t order any food. He ordered himself a Diet Coke (because he only drinks Diet Coke and water) and didn’t offer to pay for my drink. But I’m a modern woman, I can handle going Dutch (even though I do believe that, traditionally, whomever asks for the first date should pay, especially if it’s only a $1.50 soda).

I was feeling a little hesitant at this point, but I stuck with it because we were compatible in our emails. But the conversation lagged. I asked questions and he gave one-word answers…until he asked me about my feelings on the zombie apocalypse. I told him I didn’t have any, because zombies aren’t real. He launched into a 30-minute diatribe on zombies. It was at this point that I called it quits and left. Luckily, he didn’t try for a kiss or a hug.

He did keep texting me for a few weeks after. It hurts me to say that I completely ignored him, but I just couldn’t handle it anymore.

I was a junior in college and fed up with the lack of suitable guys on campus, so I turned to online dating. I started talking to M about a week after I joined the website. He seemed really nice, funny, and pretty attractive. After a couple weeks of e-mailing and texting, he asked me out for coffee, and I accepted.

I was a little late because the Metro was backed up, so I texted him when I got there about 30 minutes after I had planned. He hadn’t shown up yet. So I got myself a cup of coffee, and started to read a book while I waited. He showed up, sat down, and drummed on the table to announce his arrival. I looked up, and immediately knew that this would not work out. He had obviously very carefully selected the pictures on the website- this kid was nothing like what I had remembered. Who walks around with headphones around their neck? Seriously. On a date. He was also carrying a bucket of chicken, knowing full well that I am vegetarian. He was apparently one of those guys who thinks meat jokes are hilarious. He didn’t order anything.

We started talking, I was trying to be polite while trying to hint that I was not into the date. Then he asked if I wanted to hear a jazz band play. I love music, so I figured that there was no way I wouldn’t enjoy that. Wrong.

We got into a cab to go to the venue, and he kept trying to find excuses to touch me. When we finally arrived, he said “Oh…I don’t have any cash on me…” So I paid the driver, but he insisted on me giving him the money, and him handing it up. Ok…

So we walked to the venue, and he asked the guy at the door how we get in.

“You buy tickets.”
“Oh..you have to buy tickets? How much are they?”
“$15.”
“Never mind.”

So he turned to me and said “Well, I guess that didn’t work out”. Then he took my hand and linked it in the most awkward way possible with his arm, and said “You know, in France, this is how they walk. They’re also known for their kissing.” Um, no.

I tried to play it off, but he asked me to his apartment. I said that I had a terrible headache and needed to go home. He said that I just need a few drinks. I kept insisting that I needed to go to the metro, and that if he wouldn’t take me, I’d just walk myself. So he took me, the whole time trying to hold my hand. When we got there, he leaned in for a kiss; and I gave him the awkward cheek turn and literally RAN down the stairs to the trains.

Later that weekend, he texted me: “Uh oh…I think I might be pregnant! What should we do!?”

I never responded. He tried to text me a few more times after that. I still don’t understand how he thought that any of my actions that night told him that I was even remotely interested.

MVWD  happened when I was 23, and because both of us were idiots (mostly him). I had just recently moved to town, and thought posting a “strictly platonic” ad on Craigslist might result in meeting potential friends. This guy was my age and had also just moved into the area, so I emailed him back and we chatted online. I was flattered when he said he was interested in a date. I figured he’d end up a friend, which is what I was hoping for all along, but I was game.

We exchanged numbers and talked a couple times before we met. Things started going badly even before meeting this guy. Before making plans, I made it clear that I would only meet in our city’s downtown area, and he agreed. The day of the date, he told me what he was planning. I was expecting him to tell me to meet him downtown, but he was talking about coming to my apartment and taking me to a miniature golf course about 45 minutes away  in some town I’d never been to. I told him that I had no interest in that, and that I didn’t care if he was Jesus Christ himself – he’s not knowing where I live, and I wouldn’t get into his car and drive out of town with him. Turns out that was a rude thing to a deeply religious Catholic guy. He then admitted that he never had any intention of going downtown because before he moved, he had gotten into a pretty bad car wreck and he was nervous about driving in heavy traffic. My response was, “So, you lied? Isn’t lying a sin to Catholics? And, if you’re that nervous about driving in traffic, why did you move to one of those biggest metro areas in the country? The only way I’m meeting up with you is if you meet me downtown like you promised.” He relented and agreed to my demands.

I felt bad so I tried to smooth things over by changing the subject. I don’t remember how he segued to this topic, but he told me that he had neurofibromatosis (somewhat similar to what the elephant man had). He also mentioned that he once had a tumor that affected a nerve that caused him a lot of pain. I was sympathetic until he matter-of-factly stated that what he experienced was even more painful than childbirth, and he’s sick of women complaining and making such a big deal about it. He tells me he inherited it from his dad, who “has a tumor the size of a watermelon hanging off his ass”. He said he told me all of this because he wanted children one day and thought his potential wife should know. I’m very understanding of medical problems and physical handicaps, but he sounded like such an ass and was so crass about it all, I was unimpressed and turned off. I agreed to still meet him because I didn’t want to look like a jerk and I was kind of curious about how this would all go down.

He was about half a foot shorter than he said he was, and he had a large tumor on the side of his head that he cleverly hid in his photos with trick angles. I tried to be talkative, but it was hard to do because he’d barely respond. I was miserable. He planned dinner and a movie, but he screwed up the movie times. He suggested another movie that was starting right then, saying he heard it was good. Turned out it was “My Brother’s Wife”, a movie full of sex and nakedness. It was awkward. We got out of the movie theater, and he said that he remembered he had to do laundry and couldn’t do dinner. It was music to my ears. I said goodbye and thought that was that, but he ending up IMing me later – just chatting as if we didn’t have a terrible date. He asked me out of nowhere if I was a virgin and what my “number” was. After I dodged his question, he said his “number” was 7 or 8, which seemed like a lot for a 23-year-old religious guy who told me he was a virgin until he was 20. When he immediately started in after that revelation about how he volunteered at a Catholic summer camp for teenagers, I freaked out and I blocked his screenname.

MVWD stems from one of the many times I had tried online dating – and serves as one of the reasons that I now refrain from partaking in it. L contacted me and she seemed like the perfect girl. Attractive, intelligent, and from the Northeast, where I had moved from several years ago and admittedly miss quite a bit. After I responded to her e-mail, she gave me her phone number and we set up a date.

Within the first twenty minutes of our date, she began to tell me about her battle with ovarian cancer. Not exactly a deal breaker, but not first date conversation material. I chalked it up to nerves, but her honesty was unnerving. After hearing about her previous marriage (“We got married so that they wouldn’t take his stuff when he went overseas, but don’t worry, the divorce is nearly finalized”), her hookup with a co-worker (“I felt bad for him, he was a virgin”) and her daddy issues (“My last boyfriend was abusive, but I like a man who is authoritative”) I honestly thought she was trying to get rid of me.

She then relayed a story about her sugar daddy – who she went to Amsterdam with a few weeks before – and showed me the pictures from when she went to the sex museum. Even for a polite man like myself, I felt it was time to leave. She then ran into some guy she knew, hugged him, and ignored me. As I got up to leave, she hugged me and told me to call her so she could make me dinner that week…when her roomate/old boyfriend/soon to be ex-husband was not going to be there. I broke my “everyone deserves two chances to make a first impression” rule for her and swore off online dating for another year.

My Very Worst Date was when I was sweet, naive 16. I had met what seemed like a cute and charming 19-year-old guy online on a comic book forum and, after talking for a few months, discovered that we lived near each other (about a 25 minute drive). We decided to meet and see a movie, then go out for ice cream.

First, he showed up over 45 minutes late, which meant I had nearly given up on him even coming. We had missed the showing of the movie we meant to catch, which wasn’t such a big deal. What was a big deal was what I saw when I opened the door…and discovered the pictures he’d sent me were entirely misleading. As in, they were taken 75 pounds and a faceful of acne ago. (He was also two years older than he told me he was, which I didn’t find out until much later).

I’m not completely shallow and I didn’t want to hurt his feelings, so I bought his shady excuse for being so late and we left. We drove another 30 minutes in the opposite direction from his town and decided to have coffee while we waited for the next showing of the movie. He proceeded to buy five shots of espresso. Then he drank them all and grimaced in between each one like he was doing shots of tequila. I bought my own small frappucino and sat there awkwardly sipping it while he yammered on about how he has insomnia and didn’t get any sleep at all the night before, so he needed the espresso to stay awake. He also admitted that the reason why he was so late was because he had stopped at his friend’s house to buy some weed and had stayed to smoke a joint with him. At that point I was guessing the charming guy I had talked to online had actually been devoured by this boring behemoth.

After what felt like hours we finally went to the theater. I paid for my own ticket and refreshments; he bought a box of candy he claimed was for us to share but he literally upended the entire box into his mouth during the first preview. The movie was good; his behavior was not. His left arm immediately took up residence around my shoulders. I am a very petite girl and his arm was very large and heavy, so I was terribly uncomfortable the whole time. He tried to kiss me several times, but his breath reeked of espresso and what smelled like Doritos. He settled with nuzzling his face in my neck and hair and telling me I smelled “delicious.” I finally excused myself to the bathroom, where I called my best friend and told her if I didn’t text her that I was home within the hour to please call me and make up an emergency so I could leave. When I came back from the ladies’ room I sat as far away from him as possible while still being in the next seat, so he grabbed my right hand with his sweaty paw and clung to it until the credits ended and I insisted he take me home.

When we got in the car, the first thing he said was “So you want to make out and smoke a little weed before I take you home?” I politely declined and told him I had to get home, and he started the car. It promptly died. He tried several more times to start it before cursing, getting out of the car, and kicking it repeatedly. He then popped the hood and tinkered around a bit before getting back in. It started, and we made it around the corner before it died again.

He called a tow truck, then actually asked me to get out and help him push. Oh I got out all right… and called my dad to come get me. After all that I still didn’t want to leave the guy there alone to wait for a tow truck in a strange town with a dead car, so I agreed to sit in the car with him until my dad came. Mistake. The first thing he did was throw his arm back over my shoulders and pull me in, so my face ended up frighteningly close to his armpit. He then droned on about some inane thing or other while I simultaneously tried not to suffocate and keep him from trying to suck my face again. When my dad finally showed up I didn’t even say goodbye; I just grabbed my purse and fled to my dad’s truck as fast as my legs could carry me.

He called and emailed me for weeks after that, apologizing for his crappy car and saying that he had had a great time and telling me how “delicious” I was. Finally I gave up on being polite to the guy and told him that my dad and four brothers were going to kick the shit out of him if he ever came near my house again. To this day the word “delicious” still makes me feel a little nauseous.

My Very Worst Date was the result of my trying to “branch out” and try online dating during my senior year in college. I attended a very small liberal arts school where the dating pool was very, very limited. At the time, I had only ever been in relationships with guys I had met through school so I felt weird about meeting people in bars and going online seemed like a good alternative to what I percieved as my only other option.

Within a week of creating my profile, I received a very articulate and interesting message from “Mark” a PhD student at a much larger neighboring university. We messaged back and forth for several weeks until I finally felt comfortable enough to meet. He didn’t have a car so I agreed to drive the 20 minutes to his school instead of asking him to take the train to meet me. He was somewhat of an environmental activist and he seemed put off that I wasn’t going to use public transportation to get to our date but I explained that I needed to pick a friend up at the airport later and therefore, preferred to drive. That seemed to settle the matter… or so I thought.

I met him about two blocks away from the cafe where we had decided to go. When he first approached me, I mistook him for a homeless person asking for some cash. I’m sure I was visibly shocked as I realized he was actually my date. He was wearing a hoodie that was quite literally falling apart and some jeans that looked as though they had been washed in a mud bath. He hadn’t necessarily been dishonest about his appearance… just his cleanliness I suppose. I decided to persevere.

He briefly said hello and then began walking very quickly toward the cafe. I was practically running to keep up with him. When we arrived at the cafe he walked in ahead of me and pushed the heavy swinging door so hard that it hit me on the knee as I approached it. I don’t have any expectations about doors being held open for me but getting nailed by a door because someone doesn’t even have the courtesy to extend the handle to you is another matter entirely. I awkwardly limped into the cafe and set down at the table he had selected where he promptly told me that I “wasn’t very athletic”. I glared at him and pointed out that I was wearing heels which made it difficult to keep up to which he replied, “Oh, so you enjoy being part of the sexual second class?” I was beyond annoyed at this point but before I could retort, a waitress came by to take our order. He ordered a quiche and a sugary coffee drink. I decided to stick with black coffee and get out as quickly as possible.

As soon as the waitress left, he launched into a diatribe about his research and began a very technical analysis of an experiment he was currently working on. I listened intently as I could but became a bit despondent around the half hour mark. At that point he had allowed me all of ten words in the conversation. Even worse, he was sporting a giant whipped cream mustache for his entire speech. As the whipped cream wobbled around on his upper lip all I could think was, “asshole, asshole, asshole, ASSHOLE”. He finally stopped his rambling to inform me that I was “a worse listener than his grad students” and “not very smart”. I replied angrily that I was under the impression that this was a date and not a lecture, put down some cash on the table for my coffee and got up to leave. My chair was back up against the wall and his was out toward the restaurant so as I began to walk away he put his foot out to block me and told me he wasn’t finished talking yet and that I was being rude. I said that we didn’t have anything in common, I wanted to leave AND I needed to pee. He became more aggressive and I eventually sat back down out of fear.

He then began talking about me… more specifically, everything that was wrong with me. He started out by saying that my skin was darker than he had expected it to be and said that he thought that tanning was disgusting. I explained that my skin tone wasn’t the result of tanning but of my mother being American Indian. He rolled his eyes and chuckled at this for some reason. Then he began to dig into my clothes. He mentioned the heels again and said that they made me look slutty. He said that if I was wearing a dress for “easy access” that I was out of luck because he wasn’t going to have sex on the first date. No need to worry about that! He then brought up the whole train vs. car issue again and said that it was clear to him that I wasn’t very politically aware. This was especially annoying because I happened to be working for a local campaign at the time. Then he began to dig into his quiche… without a fork. He picked out the eggy part in the middle and managed to get it all over the front of his shirt, in his hair and on the table in the process.

I flagged down the waitress for the check. By now I had to pee so badly that I felt like I was about to burst. I again tried to excuse myself to the restroom and he again became aggressive and blocked me with his foot. A few minutes later the waitress returned with his credit card which had (surprise!) been declined. I handed her a twenty and began to plot my escape. He got up and insisted on walking me back to my car. I declined and told him that I was going to the restroom and that afterward I would walk to my car ALONE. He grabbed my wrist and proceeded to attempt to drag me out of the restaurant. Thankfully, the hostess intervened and told him that she would call the police if he didn’t leave immediately. He smirked and then left abruptly. I ended up staying at the restaurant for a bit longer to make sure he wasn’t lurking outside. Our waitress offered to drive me to my car to ensure that he wouldn’t follow me on foot and I accepted. Later that evening while I was out with friends I received a text from him letting me know that I wasn’t his type and that I shouldn’t call him. Talk about delusional…

This happened three years ago. I’ve checked the dating site again recently and he’s still on it! Beware. He’s still out there.

Three years ago I found myself single after a very long time so I decided to try online dating. I started corresponding with Eric. He told me owned a furniture store which had burned down, a great condo, a couple of cars, etc. After numerous emails and phone calls we decided to meet for an ice cream and walk around a local park. It was a warm day and he shows up wearing a heavy coat and sweating profusely. While we waited in line, he starts to comment about the tattoos on my inner wrist saying how ridiculous they looked (he knew I had tattoos and didn’t have an issue with it until now.) I blew the statement off and we go order our cones. He then tells me he didn’t have time to go to the bank and has no money. I pay the $4 and we go sit on a bench. He then starts to ask me how long I would wait to move in with someone. I was already done with the date so I told him two years.

He then tells me his ex has a restraining order against him, but “the bitch deserved it”. I could not wait to finish my cone and get the heck out of there. I made some excuse and told him I had to go. I was barely out of the park when he calls. He tells me that he thinks he loves me and can’t wait until I become his wife. I quickly get him off the phone and decide not to answer anymore calls. He blew up my phone all night. The messages ranged from asking to borrow $100 so he won’t go to jail to hoping I die because I am such a fucking whore. I saved the messages just in case and forgot about him. Fast forward four months. I accidentally answered a private phone call while getting ready for a cookout. It was Eric. He begged him to go to dinner with him. I got him off the phone telling him I would call later although I had no intention. He called me all day long. Again saying how much he loved me then moving to the die bitch routine. The last message was him masturbating while moaning my name. I took a long break from online dating.

I decided to give the online dating thing a try. The men I met fell into one of two categories: a) Nice guy, but no spark or b) Creepy disappointment. One man, however, takes the cake for the latter category. B had a profile that really appealed to me. He was seemed open-minded, articulate, and was in the entertainment business (much like myself). He said he was 5’11 and 28 years-old. After a few days of chatting, we decided to cut to the chase and meet. Having no set plans, we agreed to meet outside of the subway station which was a block away from where I lived in downtown Toronto.

He emerged from the dark wearing a ski mask… something rather daunting to most girls meeting a stranger. When he came up to me and took it off I hardly recognized him. He looked a lot different than his pictures. The first thing that struck me in that regard was that he must have been 10+ years older than he said he was, and the second thing was that he was much shorter… shorter than me, and I’m 5’6. Then he started speaking, and not only did he have a lisp, but he was missing some teeth. I’m talking prominent front teeth here. I knew right away that I wasn’t attracted to him and that there was no hope of any sort of romance between us, and I was annoyed that he had blatantly lied in his profile, but I’m a nice girl and I felt bad just turning him away at first glance.

B suggested we go hang out at my place, but there was no way that was going to happen. We ended up at a local coffee shop and began to chat. It came out that he was living out of a motel, had been kicked out by his meth addicted stripper ex girlfriend, had spent some time in jail for felonies and was a drug dealer. Dealing was his idea of working in the entertainment business!
Let’s just say that I got out of there at the first opportunity, and deleted my online dating profile immediately on my return to my apartment!