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“The Worst Date Ever!” 3 Hilarious Online Dating Fails And What Moms Have To Say About Them

We asked the online daters to share their “worst date” stories. Then we asked moms to comment on them. Laugh and learn!

worst date stories - image of a cock in suit to indicate that not every online dater is what they seem

“When people tell you who they are, listen.” – JustKibbitz Mom

In 2019, over 30.4 million American singles (and not-so-singles) used online dating sites.

For some the experience was OK, a handful were left “hopeful” and the vast majority of them, as many as 49%, report feeling “frustrated” with the whole thing, according to Pew Research Center.

The only clear consensus American online daters had reached is that lying in dating profiles is quite common.

“People [lie] about themselves to appear more desirable” – 71% of research respondents strongly agreed.

We were curious:

If most online daters are peacocking their way to a match, how can we ensure that the person we match with is truly a peacock and not another 🐓?

Caught the naughty pun?


Ok - another putz! (Pardon our Yiddish!)

Well-aware that not everyone who shines is Rihanna, we went online to listen to the daters.

These are the three real “worst date” stories they shared, along with a bit of our moms’ commentary for good measure:

image of a couple on a bad date; he is not amused by her

Not everyone who shines is Rihanna

Worst Date #1: Don’t Judge A Book By Its Job Title

One of the worst dates I’ve ever been on was off of [a dating app we won’t name]. We matched really well so I was excited about the date. We met at a hip bar near my apartment in Cincinnati.

Very quickly it went downhill.

She was a social worker but spent the first ten minutes telling me why she hated the job and poor people.

I changed the topic to music. Her quote: “I only listen to music I can cry to.”

I excused myself and went to the bathroom, where I called my roommate and instructed him to wait ten minutes and call me with a reason why I had to leave.

He did, telling me he was locked out.

I paid the tab and left.

Let’s call him Seth

Mom Wisdom #1: “Don’t take things at face value”

Someone needs to snatch this boy up!

Not only is he a planner (he had a back-up plan!), he even paid the tab before he left.

This Seth is a mensch! These traits of foresight and having financial means are not so easy to come by.

Good for you, value your time. Don’t settle when you know the date has no chance of redemption.

But also, maybe refer some mental health resources to your sad new friend?

On a different note, I found your story particularly interesting because you would never expect a social worker to be like that, just like you’d never expect a doctor to be violent, or an academic to be narrow-minded.

But then so many of them are!

People are quick to find comfort in titles and other arbitrary qualifiers, but with age you learn not to take things at face value – to be more cautious.

You hear all kinds of stories.

That’s what I keep telling [my kid]; Don’t dismiss our observations. If anything, time has made us a good judge of character.

Mama J

portrait of an arrogant young man with a crown

Lulu met a mean burger king

Worst Date #2: There Is Confidence, And Then There Is Delusional.

A couple of years ago, I matched with a guy on [a swiping app we won’t name]. We chatted online and he seemed nice so we decided to meet up for dinner.

He recommended this fancy burger bar and suggested we go for their 2-for-1 Monday special.

Now I never go into a date expecting the guy to pay for me. I'm always happy to split straight down the middle and this seemed like a great way to save for both of us!

So we get to the place and immediately he says that we won't be sharing the special, he wants 2 burgers for himself.

No biggie - not the money-saving idea I was hoping for considering the restaurant is already quite expensive but I was happy to get my own and save 1 burger for lunch the next day.

The food was great but the conversation was awkward. He kept stopping mid-sentence to ask if I was keeping up.

The bill arrives and he asks if we can split. Happy to do so, I calculate my portion and pay. I notice he has a quiet word with the waiter and gets up for us to leave.

He never paid for his portion but I didn't think much of it. On the drive home he casually mentions that his parents actually own the restaurant and he never pays there!

The cheek of it - I'm all for paying for my half of the meal but making me pay for an expensive meal at your family's restaurant whilst you eat for free seems a bit rough.

I thought that was bad enough but being polite, he drops me off at home and I invite him in for a coffee.

The guy literally DID not stop talking - and arrogant as all hell. It was even worse than the dinner conversation. All he spoke about was his wealth and his family.

When I asked questions or added in some thoughts he would repeatedly tell me that I "clearly" wasn't following his conversation but that it was understandable because he does speak "at a higher level than most people can understand."

I think this guy was just in love with his own voice.

At one stage he asked to use the bathroom and continued to talk to me FROM THE BATHROOM! I was shocked and quite frankly exhausted by the end of the night and happy to see him go.

As he walked out the door he said he will evaluate the night and get back to me. He never did message back and quite frankly, I was relieved! 😂

⦁ Let’s call her Lulu

Mom Wisdom #2: “Invest time in conversation before the date”

But how was the burger?

“He seemed nice” – Psychopaths can seem nice. Charles Manson seemed nice! This sweet girl could have put herself in real danger you know.

Meeting someone online means that you haven’t got a clue about who they are. So I’d tell her: Good for you to meet in a public place!

Not sure I would have invited him up, but maybe you were “thirsty” as my kid says.

I would say, invest a good amount of time in conversation before the date. Share stories, observe their behavior and only plan to meet when you’re really comfortable with the idea.

Mama S

portrait of a drunk man with a tie wrapped around his head

Does he like to party or is he a partier?

Worst Date #3: Gorgeous, Smart And A Giant Putz Are Not Mutually Exclusive Adjectives

I matched with this gorgeous guy. He was only visiting, but he was certain that he would move to the city in two months, so I thought the match was worth pursuing.

He is my age, beautifully eloquent and well-traveled; I was a little confused as to why would a guy like him look for a relationship online, but then again, so was I.

As we were chatting, he mentioned that he “likes to party” and that he drinks often. I didn’t think much of this because we were in our mid-20s; Everybody drank and they liked to brag about it, so I just brushed it off.

We agreed to grab a drink one evening. I waited for him in a city square for about 10 minutes when I saw him approaching. Gorgeous!

But as he approached and hugged me, he was reeking of beer – not so gorgeous!

He said “Sorry, I had a few with my friends. I’m leaving in two days so lots of goodbyes.”

“Ok,” I said. But as we were walking to the bar, he kept shouting random stuff and grabbing pamphlets from the promoters on the street. It was quite embarrassing, so I thought we would have one drink and then I would show him to the station and that’s it.

But noooo…. We had the drink, the convo was surprisingly interesting, but then when we headed to the station, he hugged me and started shouting that he’d gotten an erection!!!

I tried to shush him, but then he continued grabbing the promo pamphlets from the promoters and acting like a drunk brat.

I tried to calm him down and bear with him so I’d ensure that he’d get home safely because he didn’t know the city well.

At one point, he exclaimed that he needed to pee, and before I could utter a word, he was already peeing on a historic building, with a cop car just a few feet away!!!

I shouted in disbelief and, in response, he took a 360° turn, exposing himself to the entire square!

When I raised my voice at him, saying to get his s**t together so I can make sure he gets home alive, he said whiningly: “You are not my mom!”

I had had enough by that point and just said: “Hell no, I’m not your mother! Find your own way.” I turned and left.

I could see the cops in the car laughing and I couldn’t help but laugh myself!

⦁ Let’s call her Jenny

Mom Wisdom #3: “When people tell you who they are, listen”

Oy, Jenny, that must have been some hug! I’m shvitzing just thinking about it.

You know I think there’s a line between people who like “to party” and people who are “partiers”. For some it’s an occasional thing, and others it can be a lifestyle.

Look no judgement, but it clearly wasn’t the right match here.

And he told you so clearly and you didn’t listen. This is the Halo Effect, I learned about this in school. I was a psychology major. You give really good-looking people a pass because you think they are better than you or more right than you.

But it takes more than a shayna punim to make a match.

Two things:

Number one: When people tell you who they are, listen. They’ll tell you all about themselves.

Number two: When people tell you about people, listen. This is the problem with online dating; You don’t have that shared network who can give you a heads up.

Mama JB

Bonus Dating Advice: “If You Want To Know Who They Are, Look At Their Family!”

Two out of four moms said something to this effect, so we reserve a special segment for the good ole “look at their family” advice:

When I was young, my mother would repeat like a broken record: “If you want to know who they are, look at their family!” I remember debating her on it with passion, mostly because I wanted to believe that I was nothing like her. But you’ll see how these things catch up with you. She was right, at least in most cases. And this is one piece of advice I’d give to you, bubeleh: See where he came from. Learn about his family. You’ll see a lot of their influence on him eventually. That’s why this JustKibbitz site makes a lot of sense to me. You get to meet him through someone who has shaped the foundation of his character, so pay close attention.

“Mom, I’m not sure that you got that right,” our team member interjected. “It’s not me who would be meeting his mom on JustKibbitz – it’s you. Moms matchmake with other moms.”

Ha! Even better! Sign me up!

Mama L

What’s Your Worst Date Story?

Think you can top these? Go for it, we love a good story. 🕵️‍♂️

Send your worst date stories to


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