Jdate (a Jewish online dating site) is full of success stories. I’m a Jdate online dating success story, after all. That said, I had to meet many-a-frog before I met my handsome prince. I felt it was only right to share with you my greatest Jdate online dating flops so you could get a full picture of what I went through to meet Matt. It is also worth noting that I was the first person that Matt met on Jdate. He had no idea what I went through to meet him, but he does now…

My JDate Online Dating Disaster Stories


evan and little evan – a psychologist’s dream

Don’t worry, it’s not that kind of story (get your minds out of the gutter!).

Evan was the first guy I met on Jdate that I actually liked. He came to my house to pick me up and say hello to my parents (I would never get into a guy’s car that I didn’t know without having my parents meet him first). My mom didn’t like that he wore a pink shirt (I thought he pulled it off quite well). He was charming, attractive, and seemed to have his act together. He was only 24 and had his own apartment in Brooklyn Heights. I don’t recall what he did for a living, but I believe it was something in finance.

evan and little evan

Our first few dates went quite well. He informed me that his last girlfriend was very attractive, but not the brightest bulb in the box. What concerned me was that he said that was the type of girl he typically dated. I’m no Albert Einstein, but I’d like to think of myself as a fairly intelligent person.

After several weeks of dating we went to his apartment to watch a movie. We actually did watch the movie, for what it’s worth. Afterwards, he started talking about himself, his life, and what makes him happy.

It started off fine, but somewhere it took a turn to Crazyville.

He started explaining that it was his job to make Little Evan happy. I admit I’m a complete hypocrite because my mind went exactly where I told you not to go. He explained that Little Evan is his inner child. He then said he asks Little Evan what he should do all the time. For example, if Evan wanted a sandwich, he needed to first consult with Little Evan to find out what kind of sandwich. If he wanted to watch a movie, he’d check in with Little Evan.

This monologue went on for about 5 minutes, most of which I spent trying to hold in my laughter. I’m all for taking care of your inner child, but hearing someone refer to themselves and their inner child in third person regarding every decision under the sun was more information than I cared to know.

After he finished his speech Evan and Little Evan got me a cab. I was told that next time I came over he’d get some sour pickles because he knew how much I loved them. I’m unsure which Evan relayed that information, but I never heard from either one again. I do send both Evans well wishes.

the jdate online dating therapy session

the therapy session

I agreed to meet a guy in Sheepshead Bay (for those of you that have no idea where that is, it’s an area in Brooklyn). He seemed fairly nice based on the few exchanges we’d had. I stood outside the train station at our agreed upon location and waited. A few minutes later a guy started towards me. I am a firm believer that the kind of person you are is far more important than your looks, but the guy in front of me bore no resemblance whatsoever to his profile picture.

We agreed to walk around the bay because it was such a lovely day. Some guys are shy at first. That most certainly was not this guy. He immediately started talking. Normally I would say that was a good thing. I want to get to know the guy I date, after all. However, his topic of conversation was not one I expected to hear mere minutes after meeting him.

He started telling me that he just went through a breakup. Before I could even respond, he started telling me all about their relationship. He spoke of how long they dated, what she looked like, how much he loved her, and how much he missed her. Next thing I knew he was crying on the sidewalk with people staring at us quite strangely.

I wasn’t sure what to do, so I gave him a tissue and patted him on his back while he continued to blubber about his misfortunes.

Each time I would try to intercede, he would talk over me. I spent 45 minutes listening to his life, his woes, his failures, and mostly about his ex. I wanted to put in earplugs, but I didn’t have any on me. Lesson learned.

When he came up for air I told him that it was getting late, and I should probably head home. I told him how sorry I was about his breakup. To my utter amazement he asked me if we could go out again. The only explanation I could fathom was that he was looking for another free therapy session. I was tempted to tell him he owed me money; instead I told him that I got the impression that he wasn’t over his ex ,and he should probably hold off dating anyone until he was able to move on. He looked at me quite perplexed as if he had no recollection of his emotional breakdown. I wished him the best of luck and ran away quickly before he could confide in me about anything else.

the psoriasis, racist guy

I know this one sounds like quite the catch.

I met this gem of a man at a local diner after receiving an instant messaging from him through the jdate online dating site. He seemed nice enough at first, and he told me he liked my pedicure. Most guys don’t even know what a pedicure is, let alone notice one, but I thought it was nice that he paid attention to detail. I thanked him and we sat down.

I had become a pro at small talk from the unimaginable number of online dates I had gone on. We talked about ourselves and had some friendly banter. I soon noticed that when he shook or moved his head, white stuff fell out. I tried not to stare, but it was quite the scene. As he told me about his hobbies I pretended to listen.

What I was actually doing was stare at the pile of flakes that were on his shirt as well as the table.

It was too big to be lice or dandruff. I had no idea what was falling out from this guy’s hair, and frankly it was started to freak me out. He noticed I was staring (I’m sorry, but it had landed in clumps on the table!), and he told me that he had psoriasis. I asked him if it was painful, and he said that it was mostly itchy and uncomfortable, but not painful. Mystery solved.

Our food was taking awhile to arrive, and he was getting noticeably upset. He started complaining to me that obviously this place was run by minorities, because white people would be smart enough to have their act together. If he saw my look of disgust, it clearly was not a deterrent. He then complained that he couldn’t stand fat people, and they probably were probably responsible for the delay as well.

I told him that his comments were offensive and terrible, and I was taking my food to go. I walked out the door, and luckily never saw him again. Psoriasis was one thing, but ignorance and prejudice are always deal breakers.

the silent, creepy guy

I met this man at a coffee shop. Again, he stole someone else’s profile picture, but by this point I would have been shocked if someone actually looked like their picture. We sat down and began to talk.

To be more accurate, I should say that I began to talk. He simply looked at me as if I was speaking another language. When I asked questions, he gave one-word answers. I was a Jdate veteran, but even I didn’t know how to have a one-person conversation.

What baffled me the most was that he wasn’t giving off the shy vibe. Not only was he not talking, but as I spoke he kept staring me up and down. Frankly, he was giving me the creeps. When I didn’t speak the staring intensified. I felt like a deer about to get pounced on by a lion.

Warning bells went off in my head.

I basically threw the coffee down my throat and told him that I should be getting home.

He texted me later that evening that he really enjoyed our conversation (say what?!) and that he’d love to take me to his place next time. I felt like responding, “Over my dead body”, but I feared that might be what he had in mind.

last but not least, the mental patient

jdate online dating

I decided to save my best one for last.

Scott was a guy who lived in New Jersey about 2 hours from where I lived in Brooklyn. He was very outgoing and offered to drive the 2 hours to meet me in my area.

On our first date we had a seamless conversation. He was a good listener, had a good sense of humor, and seemed very sweet. The only caveat was that he had recently gotten out of a relationship.

I already had my share of encounters with guys who hadn’t gotten over their ex-girlfriends (Guy #2, Guy #2!), so I was cautiously optimistic about him. He had a job, but still lived with his parents, which was understandable given that he was only in his early 20s. No red flags yet.

After about a month of dating, we discussed going on a trip together.

In retrospect, I probably should have gotten to know him longer before making travel plans with him. My rationalization was that we spoke on the phone for hours everyday, and he already had told me he loved me. That was probably a red flag, but I optimistically told myself that perhaps I was just that loveable.

I payed for half of the trip, and he payed for the other half. Everything was booked, set and ready to go. That is, until I received a phone call. Scott informed me that he had done some thinking and realized he needed to get intensive professional help. He still was thinking about his ex as well as a lot of other things, and he wanted me to wait for him until he was ready to date again. To quote a line from Sex and the City, “I wanted a guy that would commit, not a guy that was committed.”

I honestly didn’t know what to say to him. Besides the mention of his ex on the first date, he never brought her up again. I told him that I had paid for half of a trip and that If he wanted to back out of the trip, I deserved to get reimbursed for my half.

There was radio silence for four months until he reached out to ask me out again.

I told him to contact me when he had my half of the money. Shockingly I never heard from him again.


My dear readers, you now have gotten a mere glimpse of the awful, the terrible, and the very, very painful online dates I endured. Some I’ve actually blocked out of my mind because they were so horrible. Many I wish I could block out, but alas, I cannot.

To anyone who is dating online, I wish you the very best as you go into battle. Some dates will make you want to run and hide under the covers. Others will make you question if putting yourself through the first circle of hell is worth it. Others may offer glimpses of hope, only to have the door slammed in your face (or in my case, the door of an outpatient psychiatric hospital).

JDate Online dating is not for the faint of heart. It is frustrating, annoying and exhausting. That said, I would do it all over again because it led me to Matt. I wouldn’t wish those kind of dates on anyone else (except maybe my husband so he could experience the horrors that I endured), but all in all, everything worked out in the end. If you are willing to persevere, you too will be able to look back and laugh (and cry) at all you went through to find the person you love.


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