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Top Five Outrageous Online Dating Stories, 2018

Robin Alexander

Posted on December 20, 2018 13:15

1 user

The stories you are about to read are true; the names have been changed to protect the guilty.

#5 That really deflating dating moment

A friend of mine started dating a woman who habitually took Ambien in order to sleep. One night early in the relationship, after a romantic evening out, she took that pill a bit prematurely. You guessed it. She fell asleep during…


#4 Why we don’t typically share dating stories with granddaughters
My 86-year-old mother had a blind lunch date with a man claiming to be 5’5”. Upon arriving she discovered that he barely reached her 5’2”. He then arrogantly informed her that he had dated 70 women in the past 2 years.

Upon arriving home, where her 13-year-old granddaughter was waiting, having come for an out-of-town visit:

Samantha: Grandma how was the date!?! 

Grandma: I won’t be seeing Mr. Peanuts again.

Samantha: Mr. Penis?

Grandma: No dear, I was referring to his height. 


#3 Killing two birds with one text

My brilliant and beautiful niece received this text from Charles: “Do you fancy a chill date with beer and Netflix? And btw, my subscription was cancelled, can we use yours?”


#2 Proof that chivalry isn’t entirely dead

My outspoken and beautiful daughter arranged to meet an interesting prospect for the first time at the Royal Pig in downtown Fort Lauderdale. She willingly made the ½ hour drive but while she was pulling into a hard-won parking spot, he texted and cancelled the date! 

Him: My apologies. You seem like a cool chick. I’m just not ready.

Her: You had me drive all this way and now ur canceling?  

Him: No explanation … I really tried.

(Lots of back and forth).

Her: You can Venmo me gas money for seriously being an a*****e.       

(Lots more back and forth).

Him: I’d like to try again.

Her: I’ll need a security deposit this time.

Him: I think you might be worth it.

(Date #2 never happened, but he did Venmo $20 for the broken date. I think she gets it from her grandmother).


This was hard. Should I write about Adam who announced he wants to live as a bisexual but have a relationship with me, or Jonathan who wanted to know if I was into S&M, or Nick who turned out to be a hoarder, or Michael who declared “From now on I devote myself to be your perfect boyfriend. I will do everything in my power, each day, to make you happy” (we hadn’t even talked).

 In the end, I chose this.


#1 Receiving the type of photo that rhymes with “pic” (proof that there are always new experiences in store, even at age 62)

Steve: Hi, what time can I call you?

Me: I’m out tonight for Rosh Hashana dinner. Tomorrow?

Steve: I have a date tomorrow night.

Me: Okay, Wednesday is fine.

Steve: I may cancel. She’s only 34.

The pic arrives.

Steve: I can’t believe I just sent that.

Me: I think you should stick with the 34 year old.


Robin Alexander

Posted on December 20, 2018 13:15


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