A few months after moving to a new city, a friend wanted me to meet her roommate who was newly-single and new to the city as well. Hearing this and knowing how badly “matchmaker” situations have gone for friends, I politely declined.

However, after several more requests and assurances that this girl was “perfect for me,” I finally accepted, but it was agreed that I’d have to see her Facebook page before any plans were made. So I did, and she was cute, active and an old social chair for her sorority. She seemed OK on paper.

We were then introduced at a dinner party for friends, and things went really well. She was, in fact, really cute, into fitness and very conversational. We swapped numbers and off I went feeling pretty good about matchmaking.

That morning, I woke up to my phone vibrating. I reached over and looked only to find that I had three texts and two missed calls. The texts started off asking if I still wanted to make plans? Did I still want to talk? Why was I avoiding her? I didn’t even check the voicemails.

A few hours later, I talked myself into chalking it up to nervousness since she seemed normal in person and so I sent a quick a “let’s get coffee Thursday” message and then went back to work.

Finally the big day came, and since I was coming from the office, I didn’t have time to change and showed up in coat and tie. She seemed to like it though, and made several joking comments about how lucky she was to be my date.

“Cool, I like your wit,” I said and quickly played the comments off.

But they didn’t stop there.

Forty minutes, eighteen or so “I’m so lucky!” comments and two life stories later, she stopped mid-conversation and announced that she had a gift for me. Then, while telling me how she wasn’t sure at first but after getting to know me better, now she was absolutely sure, she handed me a large gift-wrapped box.

When I declined because it was the first date, she said “Oh! Please open it!”

So, not wanting to be rude, I did and surprisingly, inside was a really nice sweater from J. Crew. Very confused, I looked up at her and she almost whispered, “Do…do you like it?”

“Yeah, I love it,” I said.

Then out came the bombshell.

“Good! Because I can’t have my future husband getting cold outside!” she said. “I would have totally preferred the blue on you, but they were out so I picked green instead!”

I politely declined and didn’t stick around to ask her for the matching pants.

I hadn’t been on a date for a while, so I agreed to meet a guy from an online dating site for coffee one afternoon. When he greeted me at the coffee house, I immediately noticed he had thinly plucked eyebrows, which were not apparent in his photos. He was also much shorter than his purported height of 5′9. We had never spoken on the phone, so imagine my surprise when he began talking and had a thick foreign accent. He told me he had only been in this country for two years. Again, this had not been apparent from his emails because he did not write in the same way that he spoke. I started wondering if someone else had been writing his emails for him.

On top of all this, I noticed that he was very metro in his style, right down to his perfectly manicured fingernails. While he was speaking, he was exhibiting very effeminate mannerisms and I started to wonder what I was doing on this date. More so, what HE was doing on a date with a woman. I really knew it was going badly when a homeless guy sat down nearby. We were sitting outside and I had my sunglasses on, so while my date was speaking, I found my eyes wandering over to the homeless man and I completely tuned out my date. I started checking out the homeless man and thinking he was actually super attractive under all that dirt and facial hair. I knew then that the date had to end immediately, so I said I had to go. As I drove off, I don’t think I had ever felt so relieved to end a date.

We asked you to choose an alternative winner for The Very Worst Date in America contest we ran last month. You guys and gals voted this one below the highest. Congratulations to the submitter, who received a gift card as consolation for his MVWD sorrows! And for those who missed our winning entry, it’s right here.

I went out with a girl who I met at a concert. She was a gorgeous college senior and I was working at an entry level job, having graduated earlier that year. We went out on two dates and everything seemed great. Then came the third date. I picked her up from her dorm and she immediately complained about how my car’s heated passenger seat was broken. We stopped at a gas station 7-11 so that she could get some cigarettes. I topped off the car’s fuel and she quizzically asked, “Why did you get the cheap gas?”  I pointed to the “87 Unleaded” sticker on the dashboard. At the restaurant, the waiter told us that they had an excellent (and expensive) local wine on hand so I ordered a bottle. My date flashed me a nasty look and shook her head. I asked if the wine choice was okay and she flatly said, “Yeah, I guess.” We made small talk for a few minutes, but it was clear that something was wrong. When our entrees arrived, she asked if my family owned any businesses. I responded jokingly that we were the wage-seeking types.

After dinner, she told me that we needed to talk.  I was then informed that a) the four-star restaurant we dined at was not up to L.A. standards, b) I graduated from an “unranked college,” c) my family was not “legacy-oriented” because we didn’t own any businesses, and d) my German Shepard was not an “aspirational” breed.  I was told, point-blank, that she couldn’t take a man back to her parents unless he came from substantial wealth. And, really, what would they talk about with someone who ordered an obscure B-list wine? But she would try to make things work if I got a flashier car to impress her parents, although she speculated that I couldn’t afford an Italian make (Daddy loved his Lamborghinis). Then she started to cry. Stunned, I asked what could possibly be making her cry. To which I heard, “You don’t know how hard it is! I start to like a guy and then I realize that we’re at different levels, you know, socioeconomically. America is such a caste-dominated nation.” I promptly told her that this was all very interesting, but I needed to get home so I could wake up early and attend to my unimportant job.

I was at a bar dancing with a good friend when these two guys came up and started dancing with us. I was pretty drunk and ended up making out with one of them and giving him my number. I didn’t think twice about giving out the number especially as I figured he wouldn’t call anyway. The next day he called and I didn’t answer because I really wasn’t interested. A few hours later he texted me letting me know he called. I texted back and gave some stupid reason as to why I didn’t call him back.

A few days later, he texts me again saying that it’s his birthday and he really wanted to take me out sometime. I told him I wasn’t really wanting to date. He begged for a casual meeting. I knew he lived in the same town that I go to school to, about half an hour from where I live. I had to go to class the next morning to turn in a paper and that was it so I told him I’d meet him for coffee after I finished this errand.

So there I was waiting in Starbucks for this guy and he’s 15 minutes late when I decided to text him to find out where he is. He immediately calls me and says he’s so sorry, he overslept. I told him it was fine, I didn’t really care. He then asks me if I can come and pick him up. Realizing that he doesn’t have a car, I tell him no, I’m not going to pick him up. He then asks if we can reschedule. I told him I wasn’t interested and left to go back home.

Once I return home, I saw that I had four text messages from him saying things like:

“Oh, I’m punishing myself by walking in the cold to Starbucks. Please come meet me!”

“Shit, I fell on ice and now my elbow really hurts!”

To each text, I replied: “I’m sorry. I’m at home and not interested in a date.”

He then called me and I didn’t answer. I got several more texts that day telling me how amazing I was and that he really wanted to get to know me better. After not getting any further replies, he finally got the hint.

In high school, I was set up on a blind date by my friend. She always chose good looking, flashy guys who broke her heart, so I still wonder why I allowed her to set me up.

We double dated, going to dinner first, then to a house party. My date S. was true to form, a good-looking and flashy guy. I thought things were going pretty well, and he seemed to be into me during dinner. Then, halfway through the house party, he went to get me another drink and disappeared. I looked for him for a little while, before encountering one of his friends who filled me in on what happened. S.’s ex-girlfriend had shown up at the party, and they had gone into a bedroom to have sex. I left immediately, and S. and I never spoke to him again.

The worst part was, the next day I realized that my very expensive sunglasses were left at the house.

I went on a date last summer with a girl from an online site. It started out awkwardly like blind dates do, then as she warmed up, she talked about herself incessantly. About an hour in, she started to realize that she was talking way too much so she asked me some questions. But not normal questions, like how I spent my evenings. She asked personal questions, like how my relationship was like with my mom. When I hesitated on that, she asked me if I was abused as a child. For some reason I was willing to chalk the behavior up to awkwardness and Sudafed, as she had an ear infection and all of our prior emails had seemed so normal. When we finally parted ways, she dashed across the street without saying goodbye and then called me a few minutes later to apologize, explaining that she had to catch her bus.

Then she sent me this follow-up email:

Hey!

How’s your day been? The “Car Free Portland” event was right near my house, so I rocked that for a while-felt good to be on my bike and moving again. However I think I used up all my energy in 2 hours and find myself back on the couch. I feel eternally bonded with Van Gogh because I could totally see the appeal of cutting off my ear….however, I think he cut off his ear as a gift to an ex lover. I would definitely keep my ear for myself; add some piercings-the kind I would never get while the ear was actually attached to my head-,and frame the sucker on the wall, next to the welded leg hanging across from me. Or, you know, I can wait for the antibiotics to kick in. It’s just good to weigh all my options.

This is likely the least tactful way I have ever asked someone if they want to hang out again. I just thought you being a biology major, and all,  that you may appreciate my hot talk of severed appendages. Rrrrrawww.

Get in touch?

My freshman year in high school and a junior had asked me out and I was out of this world excited. I begged my mom to allow me to go. After many promises and a week worth of house work I was given the go ahead with several conditions: he must pick me up at home and get out of the car and come to the door to retrieve me, we must tell her the movie theater and time and I had to carry my cell phone at all times. Friday rolled around and I was in my best mini-skirt outfit with nice hair and make up. He called to say he was held over at work and would be 30 minutes late. He finally showed up (I could hear his car literally squeak all the way up my hill) and came to the door in rolled up jeans and a plain white t-shirt  to my horror. I guess he was trying to look like James Dean But he was way off!

We got in the car to leave after what seemed like the longest grilling my mother has ever given and then he asked me not to roll down the window of his ‘69 Camaro because it wont go back up if I do so. At the movies he insisted I wait by the benches while he paid for our tickets. On his way back to me he pointed out loudly that they raised the prices. We proceed to the door of the theater and the ticket taker asked him for our tickets and then proceeded to laugh and state rather loudly after looking at the tickets, “Dude, taking your little sister to the movie on a Friday night is not cool.” I am on the shorter side, but hardly looked like his little sister. I asked the ticket person why he would assume I am  his little sister. He then informed me that my date had  paid for a child’s ticket for me!

I was so embarrassed at this point, but went along with this charade anyway. During the what seemed like longest movie ever made at which he tried about 30 times to kiss and/or fondle me. I got up to call my mom and get the heck out of there. Luckily, I saw my cousin in the lobby of the theater and he agreed to take me home. I left with my cousin and went dinner with he and his friends. We ended up at Denny’s sitting in a tall backed booth. Who sits behind us, but my date and two of his friends. He  was telling them in a loud voice how great his date was and how he got to second base and can’t wait to take me out again. Upon hearing this my cousin stood up and got in his face, telling his buddies what a loser he is and  how he was lying. Going back to school Monday I was dreading seeing this jerk. It turns out he had gone out on a date the afternoon before ours and had gotten mono from that girl. He was in the hospital and out of school for over three months.

Things were on the rocks with my boyfriend of over a year, so he decided to surprise me with an evening on the town. We lived in different cities that summer, so it was indeed a surprise when he showed up at my door decked out in a brand new suit. Dinner, a carriage ride, shakes and a movie were the plan. He handed me a brand new outfit he had bought for me and said to get dressed. The skirt was a size 4 (I’m a size 9), but luckily it was long enough to grin and bear at the waist without ruining his magical evening. He didn’t have a car, so we were going to walk. As soon as we stepped outside it poured buckets. He was incredibly angry, but I kept a positive attitude and said we could share an umbrella. We arrived at dinner soaked to the bone anyway, had to wolf it down to be in time for a carriage ride only to search for half an hour and find none. He had never actually checked for a schedule or location. The shake shop was closed.

Frustrated, we headed to the movies, where the indie theater was playing The Wind that Shakes the Barley, a movie about the ravages of war during anti-Brit rebellions in Ireland. Not a great date movie, but he knew I loved Cillian Murphy. Afterwards, he did nothing but rant angrily for the entire walk about how he didn’t understand the movie, the pointlessness of war or humanity’s sorry state. With my roommate mysteriously gone when we returned, I tried to calm him down with a makeout session to redeem the evening, but he was unable to get into it, raving for the next five hours about how upsetting the movie was and how sorry he was he had to sit through it. I later found out a friend of his had come while we were gone expressly to sexile my (very angry) roommate so we could have alone time afterwards, time which he spent on a political and philosophical tirade. What a waste of his own plans!

About 10 years ago, a man started pursuing me very insistently. He kept asking me over for dinner so I decided to keep it early and ride the city bus as an excuse to flee at 9pm. Dinner was plain hamburger patties, mashed potatoes and cold pork and beans. After a couple glasses of wine, he took off his hat for the first time ever and I was horrified to see he very closely resembled the actor Divine without his makeup. I kept making excuses to leave to catch the bus home, but was rather intoxicated and he somehow managed to delay me (while pawing at me and me pushing him off a couple times) until the bus no longer ran after 9pm. What happened next scarred me for life. He called his friend to give me a ride, who turned up in the local coroner’s van. Turns out they both worked for the county coroner.  Then I had to watch in disbelief while they did a prank phone call on my friend pretending to be the Jerry Springer Show, after which they told me how to embalm a body. I was trying not to panic, asking to go home repeatedly, so they told me to get in the van. He and his friend took the front seats and told me to sit on one of two empty morgue stretchers in the back. I finally made it home, but I avoided him like the black death from then on.

I moved back home to take care of my sick father, so any free time I had was very limited and precious to me. I met a girl on a dating site, talked on the phone for a few days and Mars and Jupiter aligned so I was able to be free for a Friday night. We decided I would pick her up at her place which was about a 45 min drive away. When I was about five minutes away she revealed that the pics she sent me were two years old and she had gained 140lbs since they were taken. Meaning she was about 280 pounds now. I was annoyed, but had come this far and was starving so I decided to at least have dinner and do something away from work and taking care of dad for a change.

When I drove up she was waiting outside in her driveway, wearing a pair of old sweat pants with stains, her white t-shirt was very old and virtually see through now, her hair was a rats nest and her hygiene obviously needed some work. Now I was more annoyed with this “entrapment.” I asked her if she needed to get ready and she said, “Nah, I am comfortable dressed casually.” I couldn’t have made the hints more clear and at this point, I decided, fine I’ll eat some dinner and I’m gone. She found her way into my car and we just went to a sub shop. I was prepared for a nice date, but I wasn’t about to indulge her. After we ate I said, “Well look this isn’t going to work out so I am going to head out, which way back to your place?”

I drove her home and while she tried to convince me to come inside since no one was home. I finally managed to get her out and was phone stalked by her for about two weeks until I finally had to just be totally mean (I hate doing that). She reminded me of what a great date that was and would love to do it again. I don’t think we were on the same date, or the same page or universe for that matter.