One night, a coworker of mine showed up in my office and flirted with me until I was finished with my shift and I ended up agreeing to go on a date with him. A couple days later, he showed up in my office just as I was about to get out of work. He told me he spent the whole day in bed being sick, but came because he “needed” to go on this date with me (which was totally unplanned). I was a little thrown off guard but agreed to go out with him. He had to run up to his office to grab something so I told him I’d just meet him in the lobby after I closed up. As I was waiting, he proceeded to walk past me without even acknowledging my existence, since another coworker happened to be waiting there as well. Although I was a tad pissed, I tried to understand since gossip spreads quickly in a small office. It took 15 minutes worth of cryptic phone calls to find one another.

We went to his place and without consulting me he called up a Chinese place. He got “the usual,” which ended up to be nasty mock duck with onions and noodles, all of which I hate. The whole time we ate, he asked me a lot of serious questions for a first date. For example, he wanted to know if I saw myself living in the state for a really long time because he was not moving any time soon. Right after I answered that I didn’t really know he looked at me and said, “Well, we could always travel a lot.” I was a bit freaked out so I decided to go outside for a smoke to try to think of how to get out of the situation. He followed me out and explained that I should probably quit the habit since it’s been proven to make it harder for women to get pregnant. I smoked another one out of spite.

He brought me a bottle of wine, as I was about to try to get out of this situation and begged me to watch a movie with him while he let his stomach settle. Being the nice person I am I accepted. About five minutes into the previews the sickness came back. He left for 20 minutes and came back with a handful of antacids. Then he proceeded to lay his head on my lap, sleeping through the movie as I drank the bottle myself. When the movie was over he was super upset that he missed it and that I already wanted to smoke again. When I went back in from smoking and cursing the bus system, he had passed out hard. I had no choice but to sleep on the very uncomfortable leather couch.

It was one of the most awkward mornings ever and I still see him almost every day.

I don’t mind eccentric guys, but A was extreme.

I met him at a party, and while I wasn’t extremely attracted to him, after ignoring three emails I felt bad and agreed to lunch. He was an intelligent guy, but as he was 5’4″ and socially awkward, his brains were about all he had going for him. I realized that this was especially when his oddities came out.

He couldn’t sit still in his chair. He told me that the only things he’s willing to eat, ever, are pizza and ice cream. When I mentioned that I liked traditional Russian dance, he immediately got out of his chair and began to do the barynya in the middle of the restaurant. He told me all about his romantic adventures with a “furry,” much past the point of too much information. Also anything I said, he could relate back to the Holocaust. This made things tense throughout the whole conversation. What do you say when someone twists your innocent comment into a Holocaust reference?

The final straw came when he completely out of the blue said, “Did you know that rape is technically defined as penetration of any orifice without permission?” Before I could respond, he reached across the table, stuck his finger up my nose, and said, “I just raped you!”

Eccentricity is one thing, but the gleeful nose-rape is another. I got through the rest of the date and insisted I could get home by myself on the metro. Of course, afterwards, he wouldn’t stop texting me. I finally told him it wasn’t going to work out. He texted back that he understood, which made me think maybe I was not the first girl to feel this way!

I was set up with “John,” a hockey teammate of a friend. All my pal knew was that John was cute and single. What he didn’t know was that John had an obsession with his dog. The first time I went over to John’s the dog ran up and peed on my sandaled feet. Trying to play it cool (and not punt the cocker spaniel across the room) I just said “oopsies” and grabbed a paper towel. I had no idea the dog was sending the message that I was on her turf. I went out with John a couple of times. One night, I arrived at John’s place after work, starving and ready for a relaxing evening. We turned on the TV and basically tucked the dog in for the evening before leaving. As we sat down to dinner he told me he ate a late lunch so he wasn’t going to eat, but I could get something. Awesome! I love being the only person at the table eating. He did offer to take me to the store so I could buy cereal or something. Tempting but I decided to eat there.

After picking at my appetizer and suffering through stimulating conversation including how he would make a great husband because he just likes to stay home and smoke pot or how he has to check with his mom before deciding weekend plans, I for some reason asked what adventure was next for the evening. He said he wanted to take me to a movie, but wasn’t sure if he could leave his baby home alone that long. Trying to be sensitive and not say, “IT’S A DOG – IT WILL BE FINE!!!” I suggested we watch a movie at his place. While watching the movie, the dog wedged itself between us on the couch but we somehow ended up making out and decided to move it to the other room. As I entered the bedroom, I turned around and John was completely naked holding a condom. I was completely clothed and frankly, stunned he could move that fast. Luckily, one of my greatest strengths seems to be killing the mood so after I told him we were not “there yet” we ended up just lying on the bed watching TV, me fully clothed, him totally naked. Enter the dog.

The dog jumped up on the bed and started licking John’s junk! The dog went straight for it and John did not move – like that was the most normal thing in the world. I sat there in disbelief and nothing changed until I screamed. His response was “oh yeah” as he scooted the dog away. I decided it was time for me to leave – forever. I got up and hit the road and the last thing I heard from him was “Don’t I get a hug?”

This Very Worst Date is my own damn fault. Being a wide-eyed, incredibly naive 23-year-old lands you in some dumb situations.

It (MVWD) happens after a hard break-up. Internet dating exists but hadn’t really taken off and besides, the profile business is way unromantic, right?  So I post it on Craigslist.  Mistake #1.

There are some crazy people on Craigslist. There are also (at the time) no picture capabilities. And so, it turns out, that attracts a certain type of demographic.

But that’s foreshadowing. Rewind to the emails I start to receive, some of which seem pretty promising! Intelligent and articulate professionals.  One guy is a lawyer at a good firm, and I set up a date to meet him. I don’t think to ask for a picture, or for details, because in my la-la-land head, the person on the other side of this email exchange must look…like me, right?  Normal. Maybe even kinda cute. Mistake #2.

The guy who turns up is built like an Oompa Loompa, with a face to match. He is 5 inches shorter than me and I’m 5’2. It’s like someone has set me up on a cruel gag blind date–except that cruel person is me.

But I am nice. So nice, I go through with the whole dinner date and politely laugh at jokes and then politely thank him when I leave because dang, it’s not his fault he’s only-a-mother-could-love ugly, right? Mistake #3.

My plan, though, is that when he tries to set up a second date I’ll tell him nope, sayonara. Nicely. Mistake #4.

Sure enough he calls, and I say thanks but no thanks. He asks why.  I cannot tell him the reason, so I make up anything. Everything that comes to mind. At some point I remember b.s.ing that our, uh, personalities are too much alike! You know, Type A personalities, and I’m looking for Type B…

I spend an hour on the phone explaining in every possible way I can think of that doesn’t include the words “hideous” or “ugly” that I will not date him. I get off the phone when I think he has finally accepted his fate.

Of course he calls back a few days later. I spend 20 minutes turning him down.

And then he calls again a week later. I am getting mad. But he protests that the date went so well! He’s never had a date that went so well!  That must mean something!

(At this point, ladies, I have to tell you that if you haven’t already done so, please read Gavin de Becker’s The Gift of Fear, especially the chapter on why not to let a guy down nicely.)

Long story short: I dodge periodic phone calls from him for, oh, just under a year. Despite the fact that I’ve learned (when I do accidentally pick up the phone) to cut him off and hang up. Despite the fact that every time he calls, I grow increasingly hostile and irate out of sheer fear. I feel stalked and I have nightmares that he will simply show up at some stalker-like place waiting for me.

But at no point do I say “ugly,” or “short.” Nor do I ever tell him the other thing I’m thinking, which is how embarrassed I am to have been such a dumb-ass, and sorry that I got us both into this mess.

After breaking up with an ass of an ex, my best friend persuaded me to give Match.com a try as she’d had success on it and thought I would too. I met a few really nice people off the site and managed to filter most of the booty call-type messages, but it seems one slipped through the net. His photo was good, his profile was well written and although I wasn’t entirely sure I wanted to go out with someone who was separated with three kids, I thought it wouldn’t be fair to be picky and he may just be right for me. We messaged a couple of times over the site and as I favour meeting up for a drink rather than spending months chatting online only to be disappointed scenario, we swapped numbers and arranged an after work drink and meal in town.

He rolled up late, which was fine as I knew he had a 30 minute journey in rush hour, so I’d bought a book loosely relative to the degree I am studying (criminology). He ordered a coffee, asked me if I was okay with him smoking (I smoke too, but usually make a rule of not smoking on a date) and lit up. He noticed the book I was reading and asked the normal, utterly unfunny questions about whether I was studying to be a criminal, etc. After about 40 minutes, with his coffee gone and my wine pretty much on the dredges, he asked me what I was up to that evening. I said that I thought we had arranged to have dinner, to which he remarked that he’d spent most his money today buying an XBox. He said he wasn’t really hungry but could we go back to mine?

I have a general rule that I never ever get into a car with someone on the first date, much less show them where I live, so I declined. He then spent 10 minutes assuring me he wasn’t a murderer like I read in my books, that he just wanted to drop me home. I still declined. Then he came out with an utter bombshell:

“I was hoping to get a blow job and stick my cock up your arse,” he said.

WTF? He started nervously laughing and I laughed so hard I nearly cried. When he realised I wasn’t laughing with him, but at him, he stood up to pay the drinks bill. Me, being polite, felt it was only fair to “thank” him for the date and drink so I waited for him. Five minutes turned into 10, and then into 15, and I figured he’d made a run for it, so I collected my stuff ready to leave when he appeared at the doorway. He said he’d paid for the drinks and asked me once more if I’d like a lift home.

I discovered why he had been gone so long.

“I just had a wank in the toilets, thinking about your tits,” he explained.

I thanked him, then laughed the entire way home. He rang me a few times, and texted me once to ask, “Was I a bit full on?” I never gave him the grace of replying – I’ll let him mull that one over.

I was introduced to a friend’s brother at a party and we hit it off pretty well. We each had a glass of wine and talked for hours. As a swimsuit model, I had been featured in several magazine layouts which I never disclose when I start dating someone — I just say I am a model. Anyway, he asked if he could call me the next day so we could go to dinner and a movie and I agreed. The next day he sent me flowers (he got my address from my friend) and called as he said he would. I was impressed with his consideration, we agreed to go to dinner the following night and he asked if he could pick me up at 8. At the restaurant he ordered wine and asked if he could order my meal for me, as he said he knew what I would like. I said okay, and we went back to having a lovely conversation.

During the meal he asked if he could ask me a “personal” question and when I said yes, he asked if I was a good Christian, which somewhat surprised as he didn’t strike me as religious. I replied that I was a Catholic, but didn’t go to church very often.  He then proceeded to reach into his jacket pocket and pull out a layout that I had done in a bikini bottom and no top, arms across my breasts. He stood up holding the picture and yelled, “Look everyone I’m with a slut! Who wants a piece of her after me?” I was mortified, not about the picture, but his yelling. I stood up slapped him and walked out, but he followed me through the restaurant still yelling, “Wanna see her tits? I’m sure she’ll show them to you.” I was so mad and embarrassed, but then another gentleman stood up  between us, put an arm out to stop my date from following me and allowed me to go.

As I stood outside waiting for a taxi he came out still calling me a slut and a whore. By now a crowd was gathering from both inside and outside the restaurant, with several people trying to push him away from me while he kept waiving the picture and yelling. I got a cab and cried all the way back to my apartment. After being home for about 10 minutes I could hear him outside still ranting, I called the police and while waiting for them to arrive I called my “friend” and told her what happened and let her hear her brother yelling.  The police came, quieted him down and made him leave with no arrest. The following day I received a large bouquet of roses delivered with a card from him saying he was sorry and asking if he could he see me again. Apparently after showing my layout to his friends they told him he was an idiot and was lucky to be going out with a bathing suit model.

He said he reconsidered and if that’s what made me happy he could live with that. I didn’t reply and his sister called to tell me that he called her, not knowing she knew what happened and told her that the date went “very well” and he thought there was chemistry between us. She told him that she spoke to me and I didn’t feel the same chemistry and that he shouldn’t call me again. I never did hear from him again and unfortunately his sister and I don’t talk anymore either, I think she’s a bit embarrassed and I don’t want to risk seeing him with her.

A few years ago I met this guy online, we’ll call him “Mike.” Mike and I had been talking for about two years online and on the phone before we met and he showed no signs of weirdness. We finally decided to meet up at my local mall. The second I saw him walk up I immediately wanted out. He was probably the palest, skinniest person I had ever seen and he was wearing a black trench coat in July and black platform boots. He said he was 6 feet tall, but I’m only 5’8″ and he still wasn’t taller than me, even with those horrid boots. After we walked around for awhile, he walked up to a mirror that was on the wall, took out a 4″ knife and started shaving his face with it.

We continue our stroll and he decided it was appropriate to grab me by the shoulders and lick my cheek. I have no idea what was going on in his head that made him think it was okay to do that. Then he said he was hungry, so he got a pretzel and we sat down at a table. While he was eating he grabbed my hands and got butter and pretzel salt all over them. Finally, I suggested a movie. It was a definite “boy” movie, with lots of action and guns and I figured I could slip out during it and get the hell out of there.  While we were watching the previews I felt something on my chest. I looked down and he was grabbing my left boob. It’s not like we were making out or something, we were just sitting there! I pushed him away and excused myself to the restroom and never went back. I’m just glad I made it out alive.

I was stuck in a long line at a drugstore that had just opened up after a hurricane had grazed the town. The guy behind me started making small talk, asking if we had damage and if our power was back on. I found out he was new in town, had just graduated college and started a new job. When he asked gave me his number and asked me out, I said yes. At dinner he made me guess what his new job was. I couldn’t so he told me he was a mortician at a local crematorium. I was grossed out at first, but after a run of crappy boyfriends, I decided that I should give him a chance. We all need funeral directors and it would be shallow of me to ditch him for that even if I was a bit creeped out.

The next day, he called me from the car and said he was working. I really didn’t want to know more, but he crassly proceeded to tell me about the bodies he was driving around and was horrible about them. He talked about how they died, what happened, the families and just completely violated privacy rules and human decency. When he started to explain in graphic terms what the next steps were I hung up the phone. He kept calling for a week and invited me to the crematorium. When anyone dies in our large extended family, we make sure to call the other crematorium across town.

My Very Worst Date was a guy I met on an online dating site. Right off, I had some reservations. His response to my ad sounded cut-and-pasted because he didn’t address his email to my screen name or mention anything specific about my ad. Also, he had only one picture in which he was holding a coffee cup near his head. However, he sounded normal and looked potentially cute though it was difficult to tell.

We met at a neighborhood bar in the afternoon. As soon as I saw him, I realized that the strategically-positioned coffee cup in the picture was to hide a very receding hairline. He said hello, asked me if I had biked there, then launched into a story about how he had been hit on his bike by a “rich couple” who had gotten out of paying his medical bills by taking the case to court. He then told me that he found the couple’s home address and, wielding a large wrench, asked, “What’s for dinner? You owe me.” He then intimidated the man into writing him a check for $5,000.

At this point I asked him if he had been wearing a helmet during this accident, thinking maybe a head injury was affecting him. Apparently this wasn’t the case. I considered getting up and leaving. I’ve handled my share of bad dates and was somewhat curious how much worse this one could get so I decided to stay and finish my one drink.

During the next twenty minutes, he proceeded to try to feel my leg several times, stood in the bar and lifted his shirt to show me his tattoos, told me about his last date who “throat-f**ked” him in her car and asked if I would do that. When he realized that he wasn’t getting anywhere, he got up and left without saying goodbye.

So I had just gone through a horrible breakup and with the urging of friends I joined an online dating community. This one guy stood out and my friends were there to encourage me so I agreed to meet him for drinks at a bar near my house. Everything was going okay until he started telling me how he’d turned his life around after he had been shot 10 times. I jokingly responded, “You and 50 Cent,” to which he responded very seriously with, “I know.”  I suffered through the date and its stilted conversation, coping with alcohol. Then the date came to an end and I headed outside while he took care of the tab. He then complained about the bar tab and how now he couldn’t take me to the fair because he had no more money (he worked for his parents at their family owned nursery, which was the biggest in the state). He invited me back to his house, but I said no.

Unbeknownst to me he followed me to my apartment “to make sure I made it home okay” then when I took my dog out 10 minutes later he was still there in the parking lot. I got my male neighbor to come outside with me, to which creeper responded with calling my phone quoting the Bible and telling me that committing adultery is the worst sin imaginable. I continue to get these calls every two to three months to this day.  They now vacillate between telling me I’m going to hell, him mentioning his gunshot wounds and asking me out on another date.  This date was over two years ago.