Top 10 Worst Dating Stories

‘Dating is a game’ they say. What they do not mention is that sometimes the field can get so muddy and the weather so bad that you may not even want to play that game for a very long time to come.

Here are a few of the worst dating horror stories that we have come across, written from their own experience. You would do well to avoid falling into the trap or even maybe slipping up like some of the people in the stories.

Top 10 Worst Dating Stories

Will you be My brother?

The worst date I ever had was when the woman I had gone out with asked me if I would act like her brother – apparently that turned her on.

10 Worst Dating Stories

She went full blast ahead to explain why this is in no way “shameful” and how much she loved her brother who has now left home (I can’t imagine why). I left the place at the first chance I got – definitely a date from hell and who is going back to hell, don’t you think?

The Broke Flasher

On meeting this guy online, his intelligence and honestly turned me on. I thought he was interesting, and so when he asked me out for a first date, I agreed readily. Turns out sometimes intelligence can be mixed with a weird dementedness that is really scary.

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Suddenly he begun to tell me how he found the human body to be an interesting study and how he would was looking forward to a “sweet blow job from that perfect lips” of mine – after which he proceeded to pull down his pants and flash his stuff right on my front porch.  Needless to say, that was IT for me!

The Marriage for Death

I began dating this slightly older man online once. When he came to meet me, he had a woman with him whom he introduced as his wife.

 Dating Stories

Before I could recover from the shock, the woman informed me that she was dying as she has cancer and hence she wanted her husband to find someone who could take care of him after she is gone. While this might sound sweet to some, I was at the receiving end and it creeped me out to no end!

The G.I. Joe Gal

I went out on a date with this girl who seemed to be really interested in G.I Joes. I thought it to be a little hobby of hers and even found it a bit hot.

Worst Dating Stories

So when she asked me if I would like to come to her place, I agreed – only to realize she actually wanted me to recreate a battle scene with her G.I Joe collection for hours! From then on I try to be cautious of women with slightly “different” interests.

The Grocery Girl

My worse date would definitely be the one who called me an hour before our date and asked me if I could pick up “a few” this from the grocery for her.

ten Worst Dating Stories

She said she would BB me the list and it turned out to be almost a month’s supply of everything a girl would need if she lived alone. Of course I never called her back.

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Can we Snog?

My date took me to a movie. From the time we met, to the time the movie was nearly over, he had not spoken a word to me. Suddenly he tells me, “It’s dark enough, can we make out now? You have been sitting there doing nothing for too long”

best 10 Worst Dating Stories

Boxers to Prom

My prom date turned up in striped red boxers on my prom night – I do not think any disastrous date I had after that can be as bad.

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Can you Pay?

I am not a huge feminist, but I would like my date to at least pretend to pick up the check. This guy asked me out to a costly restaurant – ordered really expensive drinks and food for us.

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Finally when the boring date was over, he asked me to pick up the check because he had forgotten his purse at home! To top it all, he asked me if I could drop him to his place which was on the other side of the city – to which I obviously said NO!

Can we Carry this Frog Inside?

I actually once had a date with a guy who turned up with a frog in his hand. At first I thought it was his idea of a joke, but it turned out that he was really fond of the frog and carried it everywhere – he even insisted that we take the frog inside the pub.

ten Dating Stories

The Worst Date Indeed

Honestly my worst date was when this new girl in my University invited me to dinner in a restaurant she used to enjoy as a kid. We drove around the block for no less than an hour and a half till we decided to eat out in a fast food joint – and voila! There it was – the restaurant she was looking for.

worst date story

I had begun to regret coming out for this lousy date but today I am glad because my worst date turned out to be the one I married and we are now together for a decade.




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