When I was in the military, I met a guy in a port call at a club. We really hit it off that night. When I was back out to sea a few days later, he found my email address in the ship’s database, and started writing me. We talked for about a month via email, and he gave me the impression that he might want to date me. As soon as I mentioned this concept, he changed his tone. The next port call was coming up. I should have listened to my instinct. I agreed to go on a date even tough I could tell he wanted something impersonal.

I checked into my hotel room, got dressed to the nines, and waited on time in front of the club for him to show up. Time was rolling by, and I started to feel like an idiot standing out there by myself. An hour passed, and the guy still had not shown up. I finally gave up and went back to my hotel room deflated. I came out of the elevator, and looked out the long picture window lining the second floor where my room is. I noticed a line of guys walking up the sidewalk. All of them were stone cold drunk and stumbling. They stood in front of the club for two seconds, and just left.

When my ship left port a few days later, the guy wrote me wondering where I had been. Apparently he spent two hours beforehand making sure to get as drunk as possible with his friends, and then said to himself, “Screw it. I’ll bring my boys with me on my date.” What a waste of time. I would have appreciated it if he had just told me that he didn’t care about me.

I met him online.  We talked on the phone for hours, had similar interests and seemed to get along quite nicely.  He lived about an hour away from me in a big city so we finally set up a date to meet for dinner at a restaurant near his apartment and then head downtown for a comedy show.  Usually a two-part first date isn’t my thing, but we got along so well on the phone that I was for it.  He gave me the address to the restaurant so on the night of the date, I plugged it into my GPS and was on my way.

I finally arrived at the restaurant address to find that it was an apartment complex.  When I called him to ask where I was supposed to be, he told me that he had looked up the restaurant online so the address must have been wrong.  He met me in the parking lot that I was sitting in (to my excitement, he was completely gorgeous) and told me there was another restaurant just up the street that we could go to.  The restaurant up the street was actually in a strip mall next to this sketchy biker bar where the men outside were cat-calling any woman that walked by.  The restaurant was scheduled to close in 30 minutes, so I suggested going to another place but my date assured me it was fine and whisked me into the empty restaurant.  Luckily the wait staff was kind enough to keep the buffet up for us to fill our plates and sit down.

During dinner, he somehow managed to get on the topic of how he hated the US government (he was originally from Romania).  He started ranting about how we spend too much money on our defense and somehow knew all this information about a military base close by that had six airplanes just sitting there, and how each propeller on the airplane was $30,000.  It was all a bit odd to me because he didn’t work for the government, so I had no idea how he knew any of this – or why he felt it was a good first-date conversation.  Trying to lure him away from the subject, I started talking about cars (one of our common interests).  It was going fine until…

Him: I love driving fast.  Man, I hate cops.  They’re all jacka**es.  I mean why can they speed on the interstate but I can’t?  It’s so f**king stupid.
Me: .. I mean, if everyone went as fast as they wanted there would probably be more accidents, right?
Him: No, I mean maybe the idiots would get in accidents, but I wouldn’t.  I’m a great driver.  I just think the social contract is stupid.  Just because we live in society doesn’t mean we should have to abide by rules.  It’s so dumb.
Me: I think it’s just how life is.. otherwise there would be chaos…

He started ranting on, and on about the government again, never letting me get two words in edgewise.  It was just a bit infuriating because he continued to bash the USA and try to tell me, an American, how corrupt we all were.  Finally, he demanded the check from the waiter by saying, “Hey, we’re done. Check.”

I hoped his anti-American rant was just his nerves, so I thought going to the comedy show would maybe get him to relax a bit and bring back that connection we had on the phone.  He wanted to ride together to the show so he asked me if he could drive us in my car (a new BMW that I hadn’t ever let anyone else drive).  When I told him that I would drive us if we were taking my car, he huffed, “Fine, whatever” and got in.  On the way to the show, he insulted my driving saying I was going too slow and if he had been driving, he would’ve been going at least 80 miles-per-hour in the 55 miles-per-hour zone.

We got to the show and sat down at the table.  The show had a two drink per person minimum so he asked me what kind of beer I wanted and then ordered four of them to cover the drink minimum.  He downed two of them in the opening act as I sipped on my one. Then he asked me “Are you going to drink that?” about the third beer.  I told him he could have it, but he wanted to share it so he poured a little into my bottle.  The comedian was great, but ironically he told a joke about people hating the “social contract” and how they were all idiots.

Comedian:  Have you guys ever met someone against the “social contract”?  Can you imagine what it would be like at Starbucks if there was no social contract?   It’d be f**king chaos in there!  People would be jumping on the counters screaming “Give me my latte!!!”  Those people should go live on their own island and see how having no social contract goes..

After the show, the first thing my date said to me was, “What was that guy’s problem with Starbucks?”

I didn’t have the heart to tell him it was people like him that he had the problem with.  I took him back to his car and didn’t see him again.

Oh B.J., the delightful soul I met through a very toxic friend when I first moved to the city.  He was older, a successful philanthropist, a business owner, and quite handsome.  He took interest in my goals and dreams of moving to NYC and expressed interest in collaborating with me in search of “young and fresh talent.”  We arranged a meeting for just the two of us.  What started as a collaboration turned into a date, which is why this particular experience is one of My Very Worst Dates as of yet.

It started innocently enough; I showed up at his penthouse ready to discuss fashion and my design background.  I will spare you the boring details and fast forward to when things really got interesting.  After about two hours of discussing projects, he decided that he was hungry and wanted to visit one of his restaurants around the corner.  The elevator ride down started with a casual mention of his interest in having not only an assistant, but an assistant with benefits.  I’m not going to lie, I was VERY attracted to this man, and although I would never subject myself to being an anything with benefits, like most women, I actually thought once he got to know me he would see me as possibly more.  Gag- well aware ladies, well aware.

Now it wasn’t the dinner that was so interesting – it was the after dinner party of two that would have made most run for the hills, but not this girl.  We retreated to the lounge of the particular restaurant, and in the blink of an eye he had donned sweatbands in full force.  That’s right, not only a very colourful sweatband on his head, but matching wristbands as well.  I sat on the couch as my colleague-turned-date started gyrating, jumping, and pounding to the musical trance emanating from the speakers.

It was so weird. So what did I do? NATURALLY I followed him back to his home and experienced awkward moment number 3.

B.J. disappeared. I went to find him, and lo and behold, there he was.  The precious little angel was sitting Indian-style in his shower with crack pipe in hand.  Apparently it was his safe place. He expressed his gratitude with me being “cool” about his escape and extracurricular activities.  He then proceeded to put the crack pipe down (ridiculous, well aware) and passionately kiss me on the floor of the bathroom.

“What are you doing on the floor?!?” He abruptly yelled at me as he jumped up to his feet.

“Umm, I’m sorry, what?”

“I have to go meet my friends, come with me.”

Again, should have left by now but people fascinate me, damn curiosity.

We hopped in his Ferrari, sped up 6th Ave, and met up with his friends. I was introduced as his assistant, slapped on the ass, and told to have a good night.

The end – no really, the end, I finally found my voice and never saw him again.

As most MVWD’s go, I met A through a popular dating site.  I was a bright-eyed, bushy-tailed, first-year university student who was relatively sheltered and very naïve as a result.  After a few messages back and forth, I decided to meet A in person and agreed on a meeting spot near his house.  The plan was to meet then decide on an ultimate destination for drinks from there.

When I arrived at the agreed-upon meeting place however, A asked could we simply have drinks at the bar under his condo building.  I couldn’t think of any reason why not, so followed him inside the cozy bar.  Inside we made small talk over the course of a couple drinks.  Though he seemed unimpressive, A seemed a decent and polite guy overall and I was open-minded.  I found it uncomfortable and bizarre though when during the course of conversation he asked if I was a virgin.  Intimidated, I casually lied ‘no,’ to which he replied ‘oh good.’  By this point I was a little tipsy from the drinks so when A later invited me up to his place for a movie, I agreed.

A refused to turn on any lights in his apartment but the hallway light streaming through the open door as we entered revealed a tidy and elegantly-decorated place.  The reason for A’s whispering became immediately clear though when he pointed out the door to his mother’s room down the hall.  Since his mother was sleeping, rather than watch the movie in the living room as I had anticipated, A led me to his own bedroom.

While he launched himself onto the nearest side of his bed, I was faced with the daunting task of either climbing over A to reach the other side of the bed, or scaling the pile of dirty laundry nearly as tall as myself.  Hesitantly, I opted for the former and propped myself up on the other side of A, facing the small tv screen at the side of his bed.  Without inviting any input from me, A slid in ‘his favourite movie,’ a black-and-white martial arts movie.  Whatever, I thought.  I’ll stay a little longer just to be polite, then make the excuse I have to head home for an early morning.

The credits were still rolling when A made his intentions clear.  Feeling pressured and a little looser from the alcohol, I played along for a few moments but panicked as he continued to escalate his advances.  Mumbling some excuse, I abruptly sat up and made my way across the bed towards the door.  A blocked my exit, but I bolted past him, over his dirty laundry, and out his bedroom.  He was right on my heels, pants down, begging me to stay, me stumbling over excuses as to my sudden departure as I tried to outrun him down the stairwell and outside the building.  Finally I burst through the main floor door to outside, leaving A behind – still with his pants down, fully exposed.

After taking a few moments to compose myself in my (locked) car, I took off.  My naïve brain was slow to process but I finally put the pieces of the puzzle together and realised this man, at nearly 30, had not yet left home, had no car and no license, no ambitious career, and no post-secondary education.

The icing on the cake is when a year later I mistakenly dialed A’s number when I intended to call a friend by the same name.  When he answered I did not immediately recognize his voice and indicated I must have the wrong number.  He asked who I was so I politely provided my first name.  It finally dawned on me who he was when his dopey-voiced response was ‘oh, well do you want to hook up?’  It was clear he had no idea who I was.  I immediately hung up and deleted his number.  I still laugh at how this momma’s boy set me up and how naïve and dumb I was to fall for it all.

After a rather long stint of being single and sexless in my early-mid 20’s, I decided to go on a string of dates via Myspace profiling (this was before Myspace became the afterthought you ignored for months before you realized the end of that era). One particular gentleman seemed to fit the “type” I was currently on the market for: mature, employed, good looking, good build, etc.

Somehow, the first date, with a lot of wine, seemed to go well and ended up in the bedroom (not something I am particularly proud of). In the heat of the moment, he said “can you feel me against your leg?” to which I inwardly thought, “no, strange, what am supposed to feel beyond your 200lb physique?” It turned out that he had a little tiny member, and that my inexperience didn’t know how to stop where this was leading. After committing, “the act” that I truly never felt, as he was inexplicably small, I was happy to end the date.

Whatever drove me to allow him to come over a few days later for a second date I can never explain, but how I got out of it goes down in history, thanks to my fabulous female neighbor/lifelong friend.

After he showed up I knocked on her door (our front doors were facing each other) and explained I needed her help out of this date. She proceeded to rush to the bathroom, smear her mascara all over her face, and grab a bottle of tequila and her pot pipe. In the meantime, I told Small Member that my neighbor was having major man issues, and she needed to talk to someone immediately. The three of us sat together on the bench on the front porch, my neighbor in the middle, as she explained, drank, and smoked her way through the most incredible tale of lies. Keeping in mind that I had to appear affected by what she was saying, I played the role of concerned friend, dying of laughter on the inside, and explained to Small Member it just wasn’t a good night for us to continue out date.

The next day I emailed him to explain I wouldn’t be interested in another date, but thanked him for being so nice to my friend in her time of need. He replied in kind, with the added response, “ya, I think you and I would have sat at different lunch tables in school.” I give him credit for taking it like a man, small member and all.

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.

Eight years ago, a good friend, “Natasha,” set me up with an acquaintance, “Colin.” She was married at the time, so it was agreed that she, her husband “Ralph,” “Colin,” and I would go on a double date.

Natasha, Ralph, and I went to meet Colin at the pizza parlor…but he never showed. Ralph tried to call Colin, but Colin’s cell phone was turned off.

N and R were newlyweds and rarely got to spend time together (he was in the Marines, she was a busy full-time student), so you can imagine how lovey-dovey they were at the time. I normally don’t mind, but when your own date doesn’t show, it’s really awkward and embarrassing.

I’d driven Natasha there (she didn’t have a car) and wasn’t about to strand her 45 minutes away from campus, so I stuck around – saying nothing about the baby talk, the kissing, the groping, making me feel like a third wheel, etc. For extra fun, the lovebirds didn’t manage to pry themselves apart for a good five hours.

The next day, Ralph called…he’d finally heard back from Colin. Colin had been arrested for “borrowing” (read: stealing) his best friend’s car! But wait, it gets worse…it turned out that Colin was a few years older than he’d said he was, had already been married twice, and had a kid with each ex-wife. I realize that’s not unusual in this day and age, but I was only 20 at the time and it was way too much for me to handle.

Ralph told Colin never to call me again. Even though Ralph later developed a bad habit of flirting with me in front of Natasha, I’ll always appreciate that.

And yes, I’m still good friends with Natasha.

When I was 17, I met this guy while working on a theatre production. He was 22, attractive, funny, charming, and flirted with me at every opportunity. However, I found out he had a long-term girlfriend. We stayed friends, and proceeded to talk over Myspace for a few months. After a while, it drifted off. About a year later, shortly after I turned 18, I got another message from him. We made plans to go out for lunch.

He picked me up from my house and we headed to a Thai restaurant. I looked at the menu, and said “I think I’ll just get ***”. He responded with, “No, I’ll order,” and proceeded to disregard my choice altogether. After we ate, we were walking back to his car when he decided to go into a Chili’s to pee (even though we had just left the restaurant). We then went to a local park, where he pulled out a guitar and played songs he wrote (poorly written and filled with swear words—which I wouldn’t have minded if the park hadn’t been filled with small children and parents). I was bored and uninterested, so I cleaned out my purse while he played. Then I mentioned I had to get home.

He drove me home and mentioned he had fun, hinting we should do it again. I laughed politely and said goodbye. He called later that week; I ignored the call and deleted his voicemail.

Two years later, I signed onto Myspace (after a long hiatus) and noticed a message from him asking to hang out since he was around for the holidays. I did not respond.

MVWD was actually with my boyfriend, “Jasper,” of 3 months. It was my 22nd birthday and Jasper’s birthday gift to me was to take me on his father’s sailboat to an island off the coast. We were going to spend the night and have a romantic time. I was very excited. Since I was the only one working (he was poor), I bought the food and drinks for the night and even splurged on a new bathing suit.

Before I go on, I must add that I realize my own stupidity in all this. Even though I was 22 I was in that puppy-dog-love stage and I thought it would be soooo romantic. The sucky part was that my best friend had plans for us but I told her I was going with Jasper instead. So stupid!

Anyways, we had to take my car since his was crappy. We drove one and a half hours to the gulf. Along the way he got an angry call from his brother demanding to know where he was. See, Jasper was in a funk band with his brother and they were supposed to play a gig that day. The funny thing was they were only going to get paid $100 for the gig- that’s between five guys. Jasper forgot to mention to his brother that it was my birthday. Even while his brother was screaming and cussing at him he never mentioned it was my birthday. When I asked him why he never said anything about it, he claimed that his brother would not care because he hated all women.

We got to the sailboat, just to get another call from Jasper’s father asking why Jasper was taking the sailboat without his permission. Luckily his father understood and wished me a happy birthday, so off we went. I was so excited and was daydreaming about how much fun and romantic this would all be. My daydreams were ruined when Jasper suddenly asked me if I would mind turning back around so he could go to the gig. Instead of telling him he was an idiot, I was too hurt and shocked to even say anything. I just turned my head as he told me that it was going to be so much fun sailing on our way back. So I sat there with tears in my eyes and $60 worth of food and drinks wasted on this wuss who couldn’t stand up to his brother.

The drive to the gig was even worse; it was my car, but Jasper drove it because he knew the way. He was speeding and driving my car like a maniac. I screamed at him to stop it, that it was my car, and he would pay if he damaged it. He apologized and told me he had to get there on time. I screamed at him that it was MY birthday and his brother and him could go f*ck themselves.

We arrived at a HOUSE, a house, not a bar, and the gig was for a family. I was  more than livid and I grabbed my keys and left. But then I got lost in the maze of houses for 30 minutes, so I called him to ask for directions. He gave me directions. Lo and behold, they were directions BACK to the house so I could pick him up because his brother did not want to drive all the way to his apartment. Stupidly, I agreed.

The only good part was that I got to scream at him the whole way there and dropped him off at the edge of the street of his apartment complex so he had to walk.  After that, I called my friends and was able to salvage a half-way decent birthday. Naturally, Jasper was enough of an idiot to assume we were still together after all of this. While I was out the next night finally celebrating with my best friend, Jasper called me and asked me why I was doing this to him- as in why did I break up with him. My friend grabbed the phone, and I don’t recall what she said to him, but he stopped calling.