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And the Winner Is! The Worst Dates We’ve Ever Heard

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The Single Life

And the Winner Is! The Worst Dates We’ve Ever Heard

If you thought you had a bad date, these worst date winners take the cake.

As a love and relationship digital magazine, it is only fitting that from time to time we pay homage to some truly horrible dates. We researched and dug deep, and just like a beauty pageant we decided to crown a first place winner and a runner up.  I’m Trump now, bitch!

PLUS: You’re Thirsty! 6 Desperate Things Men Do on First Dates

The following may just be the baddest, the craziest, oddest, and the most shocking (in a funny way, of course) dating stories. First, third place:

The Guy with Anxiety

Anxiety Big Band Theory


An open-minded woman and an equal opportunity dater, Tabitha, 38, from Philly, thought nothing of dating a guy with severe anxiety. “He didn’t like to go out in public,” she shared, “and even had to get a doctor’s note so he wouldn’t have to work because it gave him anxiety attacks.” So when he asked her over to his place for a movie date, she understood and happily accepted. “I got to his apartment [for our date] wearing what I thought was a stylish outfit, but he looked at me and said ‘Oh no, where did you get that sweater? It has lunch lady pockets and looks like a lint collector – and did you dye your hair? You look like a soccer mom right now.” Insulted, Tamara proceeded with caution yet didn’t leave. He escorted her into the living room where the only furniture was a tiny TV and a Star Wars inspired cot. Then there were his walls. “Sayings like, ‘Be kind to others’ were scribbled in permanent marker. I thought I had entered the den of a serial killer!” Tamara knew it was time to dash and texted her brother “yellow” – their ‘save me’ word. Her brother caller her in the knick of time. She was out of there before Mr. Anxiety trapped her in a closet.

Now, the runner up…

Hooker for Hire

Hooker RuPaul

GIF: Logo TV.

A newly single 24-year-old man was excited to begin dating again. “I  met a nice enough woman,” said Jose from Miami. “So I asked her out to lunch.” They make small talk to get to know each other when she asks what he does for a living. “I tell her I’m a bartender and am studying for my actuarial exams, and ask her about her line of work. And she says (brace yourselves): ‘I’m a hooker.'” A hooker?! He should’ve slipped right into a body condom.

But, wait – the next dating tale is actually worse. Yes, this is the winner!

The Not So Divorced Divorcée

Britney Confused Face

GIF Credit:

“I knew a man for about a year and he asked me out on a date,” shared Linda, 32, from NYC. “While on our date, he began talking about his ex-wife and his child.” Suddenly, he mentioned another child, so she asked how many children he actually has. “He says, ‘ I have two. One is 3 months old.’ That’s when it hits me. Did this guy just divorce his wife?” Linda pried,  “Who is the baby’s mother?” To which he replied, ‘My current wife.'” Apparently, homeboy doesn’t believe in monogamy. “So, I asked one more question,” Linda continued, “Well, why are you married then? And he answers matter of factly, ‘Because I love her.'”

WATCH: Ask Sujeiry: Leave a Date If There’s No Chemistry?

What a two-timing macho douchebag. Since I’m Trump now, all I have to say is, “you’re fired!”

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Sujeiry is a natural storyteller, dynamic radio show host and the proud CEO of She's been at this digital media and content creation game for 15 plus years and pours her heart and soul onto - the only site for Latinas on all things love. After realizing there was a void in the love/relationship Latina media market, she took matters into her own hands and became the go-to sex and relationship expert on Latinx platforms. The former sex and relationship expert on works diligently and passionately to encourage women of color to be their authentic selves as they navigate all things love.


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