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CITY's Worst Date Contest: Winners Announced! 

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Winner: Joe G. I met a girl one night on Bumble. She was cute and seemed like she had a lot going for her. We hit it off and I suggested dinner. We went to an Italian restaurant for our first/last date called Rocco's on Monroe/Marshall St. She brought with her a pumpkin spice latte from starbucks up the road. We sat at the bar and I even remember the bartenders name (Christian). She had her cup sitting on the bar like that was a normal thing. She told the bartender how hungry she was and that all she wanted was spaghetti and meatballs while she casually sipped her drink. He suggested an appetizer and she made it a point to order another meal to go for later. When she got her meal she chewed with her mouth wide open, smacking her lips. This was followed by a litany of ‘Mmmm’s” and “Nom’s” I thought I was dating the fucking cookie monster! When we were done she licked her plate clean of all sauce. Everyone that had to walk past the bar to get into the dining area did double takes and what only lasted about a solid minute felt like an hour. The bartender kept asking her how she liked her meal in an attempt to have her come to her senses, but she had no shame in her feeding frenzy. Embarrassed, I never went back to that restaurant since. I cringe at the thought that there is a fool that had a worst date than me, if so they deserve to win this contest.


2nd Place: Abby P. When i was a freshman in college, a boy on the track team asked me to go on a date. He drove me to a bar where his fake ID was denied and then drove us to another bar where he KNEW his fake would be accepted. He preceded to have 4 drinks in the time it took me to have one glass of water. He then directed me to our next location... a party at the basketball house. He left me to “go get us both a drink” and when he didn’t return for 15 minutes i went to look for him... he was making out with a girl who lived on my floor. On the way home, he puked... all over himself.

3rd Place: Brian P. We went to a local pub. Immediately, she began to voice her distrust of people of color. She then went on to tell me that her beer glass collection was getting low and began filling her purse with Quinness glasses. OK, time to go. Back at her home she was insistent on introducing me to her full-grown mastiff. He was very territorial. She poured a glass of wine and we adjourned to the living room. The dog sat on the floor staring at me. When she went back to the kitchen for more wine, the dog lunged on to me and sliced open my lip that would require sutures. That’s it … I’m out! It can’t get any worse, can it? As I head for the door, she’s questioning me on what I did to the dog. Really??? Holding paper towel to my gushing lip, she asks me why I want to leave? Isn’t this obvious I reply? She continues, I will put the dog outside and was hoping you’d stay so we can make out. Clearly, you don’t have a grasp of the situation. Out the door I go to urgent care to lick my wounds.

There were lots of great stories submitted, but we could only pick 3 winners. You can read the rest of the submissions below:


Christine F. When it comes to dating (actually, in general), I’m unbelievably awkward. I’m also a recently divorced mama. My friends encouraged me to download Bumble, and I painfully obliged. I matched with a cute guy; older, covered in tattoos, hilarious to a fault. Perfect, right? I was cautiously optimistic because we’d hit it off previously at Good Luck, and he remembered me. One downside - he’s a little short, but if I didn’t scare him off when we met, I could let it slide. We spent two months together until the absolute worst date ever happened. On his last day of his job, we got drinks with his coworkers. Cool! Meeting his circle. Good sign, right? Wrong. He spent the entire night talking to anyone but me - including his ex. It’s like he forgot he invited me out. I can hang with the guys, but you shouldn’t feel completely insignificant. With the courage provided by the 3 Gilded Rickies that I left on his tab I said “I’m going to call a Lyft- you clearly don’t want me here”. He said “Sorry, I’m networking”. Cheers to not always having the best luck at Good Luck. On to the next one!


Katie C. About five years ago, I began dating a Professor of mine. Now I know what you are probably thinking, but I was 32 and he was in his early 40'S. He took me out to a wonderful dinner with his sister and we all hit it off really well until I went back to his house and saw tons of pictures of the two of them together- a little too close for siblings. When I questioned him, he told me she was actually his wife! As if that wasnt bad enough, she went along with being his sister and then told me she liked the man he had become since dating him! Needless to say, our relationship did not last.


Jeanie B. There was this good-looking guy who worked in my complex as a maintenance man and when the opportunity arose I said, “We should go out sometime.” He accepted my offer and we planned our 1st date. I was excited to get things in motion #literally! I met him at a restaurant where he was waiting at the bar and hadn’t been serviced yet. As soon as I walked in the bartender offered me a drink, still ignoring my date which enraged him. We went next door to another restaurant where he tried to complain about the food to reduce the check and then left a dollar tip! (knowing I’m a waitress #Smh) Our final stop was a local dance spot. About 10 minutes into getting my groove on he starts yelling at some girl for apparently giving me a dirty look. I was so embarrassed and couldn’t even finish my drink before he said we’re leaving. On the way home he seemed intoxicated and right as I pulled up to drop him off he pukes up chicken wings in my recently detailed car. Offering me $20 and we never spoke again!


Sarah H. I was meeting up with this guy for the first time and we were going to my favorite restaurant near my college.Family owned, have the best brick oven pizza around. He showed up 30 minutes late, insisted we drive separately to the restaurant (understandable, we have a different commute) criticized me for drinking out of a straw, when I finished my meal commented and said "wow, you ate that fast!" and when we ordered dessert, told the waitress who made the cheesecake that it was too dry to her face. I saw the tears in her eyes. Needless to say, we didn’t make a second date.

Joey M. When I was in college, I went on a date with a guy from a neighboring school. We had a good time walking around his campus as we chatted about theater and Harry Potter (we are both die-hard fans). At the end of the date, he leaned and kissed, but he stopped after a few seconds. When I asked what was wrong, he said, "I'm thinking of somebody else." I immediately said goodbye and I walked to my car totally embarrassed. To make matters worse, he insisted on following me to my car, apologizing profusely. In a truly dramatic gesture, I rolled down my window and said, "That was really mean!" before I sped away. If that wasn’t bad enough, I found out later that the guy he had a crush on went to my school…was in the same theater program with me…and was also named Joey. I eventually told "the other Joey" the story and we laugh about it sometimes. At least I gained a friend out of it.


Nia G. Last year i went on a date with this guy. He seemed like a nice guy. We went to the movies to see the Accountant. I thought it was a good movie. He bought me food and candy. He kept getting up the smoke and use the bathroom. Towards the middle of the movie he said that he had to handle a situation. He said that he would come back for me. I said what why would you leave me i dont have my car. He said he will be back to pick me up. I told him i would go with him he said he would rather i stay and finish the movie. So i said ok and finished watching the movie. After the movie i called him and he never answered his phone. So i left him a really mean message on his phone. Im glad i had some money so i called a cab home My worst date ever


Kathy S. Met him at an art opening; not my type. He followed me form piece to piece, talked my ear off, gave me his number saying, “I bet you won’t call.” I should have proved him right, but I called just to prove myself wrong—maybe he’s not so bad, I thought. I drove to pick him up, finding out he had no car, only a bicycle. Before our hike, he stopped at his aunt’s place and stole a bottle of wine. In the woods, he began to tip over trees that were dying. It was strange. When we ate lunch later, I paid…he had no money—none! He ordered seconds on the fries. He had free tickets to a concert, I paid for parking--crappy band. Later, back at his place, he showed me photos he’d taken in Israel while living on a Kibbutz. They featured crotch shots of girls on a beach; they were unaware he was taking these photos, eye-level, between their legs as they sunbathed. I said, “good-bye.” Months later, he saw me and said, “hope you enjoyed that wine I left in your car,” as if I should have returned it to him.


Isaiah C. In 2008 I was at Wegmans and saw a beautiful brunette while waiting at checkout. I struck up a conversation and to my delight, things went well. I got her number and we agreed to meet up again. A week later, I met up with her at Spot Coffee and everything went great. Then she said she loved sensual, and nude art. She said she has a lot of this very kind of art at her place on Park Ave and I was welcome to go over and take a look. Intrigued, I agreed. In her nude art filled apartment, we decided to watch a movie. Only 10 minutes into the movie, we suddenly hear a loud pounding and yelling at the door. I hear a man yell “I know you have a guy in there!” Embarrassed, the girl said, “That’s just my ex.” Not wanting to go any further down this rabbit hole, I started to excuse myself. I opened the door and told the ex-boyfriend, I wasn’t even that interested in this girl and that I’d only just met her. The girl got pissed at me and tells me to get the “F” out.


Laura T. Around the time Miley Cyrus chopped her locks and sported the short blonde look, I opted to do the same in an act of stretching my newly found freedom and rebelling against my family - just like many other girls mimicking the look. So, my hair took a while to grow in and was very awkward for a time. I went on a date with a young man I had been talking with on OkCupid to the movie theatre near me, and we had never met. The date started out incredibly awkward because we just weren't connecting and it was painfully obvious he "just wasn't that into me". Of course, the movie I had chosen to see was Captain Phillips, also known as the tear jerker of the century. By the end of the movie, I was blubbering and couldn't stop tears from flowing down my face which made things a million times more awkward. Needless to say, he didn't talk to me again after that.


Helene S. I meet someone many years ago at a dance . We set up a date to meet for dinner . He picked me up looking like he slept in his clothes and to top it off he had no socks on . It was not cool back then not to wear socks .,we went to eat somewhere that I can't remember the name of it but it was attached to a gas station . To top it off he couldn't remember my Name kept calling me Helen , Elaine or recd I have red hair . Needless to say I was afraid to drink out of the glass let alone eat there . That was my first and last date with what's his name.


Rachel O. I was living in Toronto and he was living in Rochester, and we agreed that I would stop by and meet him on a visit somewhere else. He knew I was in graduate school and I worked in a social science department that had a strong leftist leaning. He had a landmark to show me in Rochester, he said. It was a great magazine shop with all kinds of interesting periodicals, he said. He drove around and around in circles, because he had no GPS or cell. We continued circling; as it got later, I suggested giving up and getting dinner. At some point, even though I was dressed up, I insisted that he stop to let me pee at a downtown McDonalds. There was no other option, and inside, there was no toilet paper. When I came out, I said, “Let’s just get dinner.” “But it’s so cool!” he said. “I really want to show you!” And, finally, we found it. World Wide News. We walked in, and yes, there was a Socialist Register and a New Left Review, but they were on the shelf behind all the grey-haired men standing and peering into other magazines: those with pornography.


Campbell C. When I was 16, a boy that I really liked from school ask me out on a date. I was super excited, because not only did I really like him, I had never been on a date before. We agreed to go down to the canal and ride bikes, and then get some ice cream from the dairy afterward. I thought it sounded wonderful. The first red flag was that he showed up at my house with a tandem bicycle. I had thought that we were each writer separate bikes, however he wanted us to ride the same one. Romantic, sure. The problem was that he is 6’3” and I’m 5’0”-so when he rides the bike my feet don’t touch the ground. I just hung there knowing I couldn’t balance myself. That meant that we couldn’t stop because we would fall over. After some moderately reckless bike riding, we arrive at the canal and go for a little walk. It’s all going well, and he suggests that we go get ice cream. While this is certainly something that’s open for debate on many levels, I had expected him to pay for the ice cream because he had suggested it and he had invited me on the date. He also didn’t ask me to bring any money. I did, just to be safe, so when he didn’t pay for me I was able to pay for myself. The absolute worst part was at the end when we were headed home. He jumped a walk light and we ended up getting hit by a minivan. The best part? It didn’t hit his half of the bike, only mine. So while I go flying off the bike, he balances himself and continues unfazed. I landed on the ground in the intersection. I leapt up and ran to the sidewalk, where I proceeded to panic about what had just happened. My leg was bruised and I had scrapes on my arms and hands. I refused to bike the rest of the way home, so he walked me there. We went on a few more dates after that, but eventually he came out as gay. I didn’t ride my bike for a few months after that.


No Name: Ok... so I first have to say that I haven't had a whole lot of luck when it comes to dating and/or love. I have some real horror stories about a lot of men that I have met throughout my life, HOWEVER, I would have to say that the very "WORST DATE" I've ever been on goes like this: I went on a blind date in the summer of 2016. I have never been a huge fan of online dating or blind dates but I thought I'd give this one a try. We met at a restaurant for dinner and things were going well. Conversation was flowing, we were laughing and getting along fine. As most normal "blind dates" go, you tend to ask a lot of questions. The one thing that I felt was a bit off was that I wasn't getting many responses back from my date regarding his family, work history, past relationships, etc. At first I thought he was just a very private person and didn't feel like sharing much information with me on the first date. I can respect that and didn't think much of it at this point. As for me... I'm an open book. I have no secrets or skeletons in the closet. My life, thus far, has been very normal and somewhat boring. I have nothing to hide... During our dinner I felt at ease and comfortable with this man. I really was having a nice time. It was pleasant and fun to be out enjoying a meal with someone. And then..... B A M !!! I don't even know how this came about OR what possessed him to tell me BUT ... He started off by saying that he really liked me and that he felt a great connection between us so he felt the need to be totally honest with me. I sat there very contently listening to his every word. He told me that he hadn't been in "Rochester" for quite a few years and he has had very little contact with his family and friends. I'm thinking to myself "ok...he had family issues and just lost touch with everyone". He continued to talk and then the truth came out and it hit me like a ton of bricks. His words ... "I have actually been in jail for the last 30+ years and just got out recently" EXCUSE ME... WHAT??????? is what I was thinking! I thought for sure I misheard him! So I asked him to repeat that and once again he told me about being in jail. "Are you kidding me right now" is what I said out loud while laughing nervously! With a total straight face he told me it was the God's honest truth. Oh my God... WTF!!!!!!!!!!! Nervously I just HAD to ask..."what did you do????" "I was "accused" of killing someone" he replied. Nervously I sat there ... still nervous and laughing (yes I laugh when I'm scared & nervous). I continued to ask him questions like "what's it like in jail? Is it like what you see on tv? Do you know how to make a shank? " Then I asked... "what happened to the guy that was killed?" His response... "it wasn't a guy...it was a woman!!!!" OMG!!!! Now I'm really ready to RUN and RUN FAST!!!! There was more that was discussed that I wish not to share to protect his privacy & my safety, HOWEVER, I have to honestly say that this was definitely the worse (crazy-ass) date I have ever encountered!!!! With all of this being said... I would like for my name, etc not to be shared to protect myself. He KNOWS where I live. I don't want to be looking over my shoulder for the rest of my life!

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