One night I met friends to have a nice, quiet cocktail and some good conversation. Instead we had too many cocktails, danced and flirted with all the cute boys we met. I made a game time decision at the end of the night to say goodnight to the ladies and left with the guy I was dancing with all night. Turns out Mr. Wonderful was an unemployed struggling musician who just got fired from his bartending job at a douchey night club. You’d think that would be enough for me to rethink this little venture, but no, I was a real glutton for punishment that night.

We got to his house, which was just a short walk from my favorite coffee shop (which happened to be around the corner from my office). Making small talk I noticed a few pictures of him holding a baby and I remarked on the baby’s cuteness, to which he replies that it is his, and he’s a month old. He then told me that his baby momma lives in Wisconsin, which is too bad because babies are great for picking up chicks. I was rendered speechless and then I noticed he was pulling out the futon in the living room. Taken aback I asked what he was doing. Turns out he sleeps in the living room here because he just moved in with his dad and he doesn’t have a bedroom. WTF? Who brings a girl home to the couch in their dad’s house? The look on my face no doubt betrayed my horror because he said, “No worries, my dad’s cool.” Then he gestured to his gigantic bong that was sitting on the coffee table.

In the morning Mr. Wonderful told me a hilarious story about how he was planning on going over to his ex-girlfriend’s place, but then he met me and I’m “way hotter than her” so he changed his game plan. I’m thinking this whole scenario can’t get any worse. And then it did. I asked for him to give me a lift home, but he said he couldn’t because he and his dad share a minivan and his dad took it to work very early this morning. He’d be home at 11am at which time Mr. Wonderful could drive me home. I didn’t really like this plan. For one thing, Mr. Wonderful’s dad had already seen me asleep on the couch, when he left for work. I didn’t want to have to make awkward and polite chit-chat with the dad when he got home from work. While I rethought my exit strategy, I asked what his dad does to work such odd hours.

Turns out that his dad is my favorite coffee shop guy. Serves me right.

MVWD  happened in my second week of university.  I’d met a girl through our LGBT (lesbian, gay, bisexual and transgender) organization who seemed nice enough and was quite pretty.  We were in the same halls of residence and one evening she asked me to come up and watch a film with her. When I got up there she had some music on and asked me what I’d like to listen to. I was neutral and suggested something I figured she’d like based on what was already playing, to which she promptly ignored the idea and put on something else.

Then she asked me which film I would like to watch. Being a bit of a film snob (apart from my love of Mean Girls) I wasn’t impressed with the DVDs she had in her room, but it was fine, and we settled down to watch the least gross-out comedy-type of the bunch: White Chicks. That was when she started talking about “lovely” girl she’d met and slept with the other night, but this other woman had gone onto reject a relationship with her. This went on for a while with me nodding and trying to stay awake until she ended the diatribe with “but I think you’re really pretty.” Bored, looking for some action, and not wanting her to pile issues on me again, I kissed her.

So we were making out for a while and it was fine. She took off her top, but then when I went to actually touch her down there she jumped off me and burst into tears. It was then I found out she was in love with an American girl who she’d never met or heard the voice of on the internet. This is where the “date” should have ended. Unfortunately, I listened to her woes and tried to help her out, gave advice and all that for what felt like five-plus hours. She asked if I would stay over (bear in mind she was still topless here) so we spooned and went to sleep, but not before she made a jibe about how my fingers smelt of cigarettes.

The next morning as we left her block she saw someone she’d befriended and convinced me to kiss her right there. And I did. And then went back to my room feeling pretty used and pretty confused.

As a junior in high school, I worked at a local fast food chain and they hired a new student to work the grill. I was one of the few girls to work the grill and we became friendly. I thought he was very cute–tall, blond hair, blues eyes and he drove a sports car that he fixed up himself. He went to a different high school than I did so I thought nothing of it when he asked if he could pick me up from school one day. I just figured that he had half day.

When he picked me up, he looked great but his car sounded terrible. It was so embarrassing that I actually waited until all of the buses left and most of the students were gone so no one would see me. He then proceeded to use the word, “dude” about a thousand times! Hello! I am a girl.

To make conversation, I decided to tell him about a great debate we had in my history class. When I finished, he looked at me like I was talking another language, switched the subject and proceeded to tell me how he skipped school that day, like he often did.

We were supposed to go bowling but I had a better idea. I knew that this was going nowhere fast so I suggested that he come into my house while I changed and speak to my mom. They spoke while I was changing. My mom and I then talked a bit about my class debate.

He looked at me, I looked at him and he told me that he was not feeling well and asked if he could take a raincheck. I told him that was fine and that was the last that I heard of them. My mom helped me to get out of a tight spot.

Sad thing is that he dropped out of high school.

My Very Worst Date happened at the beginning of my dating career. I thought I was a goth kid and therefore saw no issue in dating a dirty 17 year-old kid with washed-out blue hair and a bad unibrow. We’ll call him K. We hung out at his house before going out (of course, his room was in the basement) and my first alarm should have gone off when I saw the scantily clad anime girl poster covering an ENTIRE wall. He readily admitted that he watched hentai (cartoon porn), but me being in total denial of that being weird, I said nothing. We ended up going to a movie and wandering around the downtown area afterward. We were sitting in the grass and the date was actually going quite well. We were laughing and joking and I playfully smacked his arm for some reason. He moaned and admitted that he was a masochist and asked me to hit him again. I did not. For some reason, I dated this kid for about three months, which ended in a fight where he left 20 something crying messages on my cell phone when I went to take a 15 minute shower. I told him to grow some balls and call me back when it happened. I haven’t heard from him since.

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.

When I was in the Army, I was stationed in Arizona for a few years. I met a girl, Sally, at the local bookstore, and wound up having a conversation with her every time I wanted to buy a new book. I got the nerve up one day to ask her out, and, knowing that she was a horse enthusiast, decided that it would be a good date idea if we went to the fort and rode horses (there was a corral where you could rent horses for the day).

I should point out that I am a born and raised city boy. I hadn’t even seen a horse until I was sent to Arizona at 19. Sally got onto her horse with practiced ease. It took me almost ten minutes to get onto the “U” shaped glue factory candidate the rancher called a horse. About five minutes out, my horse decided he had enough and started trotting back to the corral, at which point I tried every idea I had to stop the thing. Nothing worked. As I mentioned, I am a city boy. I had figured a horse was like a big dog.

I panicked, because the horse was moving at (to me) a pretty good speed. As the horse entered the corral, I yelled to the rancher, “Is there any way to stop this thing?” To which the rancher replied, “Well, if he hasn’t stopped yet, he will when he gets to some water.” The horse went inside, I climbed/fell off of it, and then came Sally, riding the horse without any difficulties, having witnessed my terror at riding a horse. I attempted to salvage the date by making a few jokes about it, but evidently I was not manly enough for her.

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.

This is not quite a MVWD story but the Very Worst result of a date that happened a while back.

I was at a charity event with my best friend. There was music, cocktails, and lots of people mingling. She was talking to a guy and I went over and joined the discussion. It was really loud in the room, so I introduced myself to the guy. He kept looking at me and then said something, which I couldn’t understand. I asked him again for his name, when finally my girlfriend yelled in my ear, “You dated him, dumbass!” I was mortified.

Twelve years later, no joke, I met a guy friend of mine at a bar with one of his buddies. He introduced me, I said hello and chatted for a minute. As we were talking I said, “You look sooo familiar to me…” The guy responded, “Yeah, we dated.” It was the same guy I had forgotten at the charity event all those years before. How embarrassing.

During college, I dated this very cute boy one summer and was sad that he was going to Japan for the school year. He asked me if he could write me and I said yes. He started writing me about once or twice a week throughout the school year and I was totally excited about his return. He asked me to meet him at the airport, but I told him I couldn’t because of my work schedule. At the last minute, I was able to reschedule and surprise him. He seemed oddly distant at our reunion, but I explained it away because of the jet lag. We went out once after that, but he spent the whole time talking to some friends he saw and the next table over.

In the meantime, I went to a party of a friend who lived in a nearby town. Her younger sister was an aspiring model and I was an aspiring photographer so we agreed to to meet up for coffee. At the coffee shop she started telling me about this great guy she knew who had gone to Japan, but had written her nearly every week. She said that she was supposed to meet him at the airport, but couldn’t do it because something had come up at the last minute.  Yes, it was the same guy and we had both dated him around the same time the previous summer. When I confronted him, he said that he didn’t want to break it off with either of us and hoped that things would work themselves out naturally.  They did and now and the other girl and I are Facebook friends, but not with him.