The Dating Cesspool: The WORST!KIND Quick Guide in dating

Posted by Jaesen Keith on

Dating can be an adventure filled with ups and downs, excitement and disappointment, laughter and tears. While we all hope to find that perfect mate, sometimes the road to love can be paved with some of the most hilariously terrible dating experiences. In this blog post, we'll share some of the worst but funniest dating stories and provide some tips to help you navigate the dating world and find your perfect match.

Watch for these Red Flags

Before we dive into the funny dating stories, it's important to keep an eye out for some red flags that could indicate a dating disaster waiting to happen.

  1. Lack of Communication: Communication is key in any relationship. If your date is unresponsive or doesn't show interest in getting to know you, it may be a sign that they're not invested in the relationship.

  2. Disrespectful Behavior: If your date is rude, inconsiderate, or dismissive, it may be a sign that they don't respect you or your time.

  3. Inappropriate Conversations: If your date is constantly talking about themselves, making inappropriate comments, or sharing too much personal information, it may be a sign that they lack boundaries or don't understand social norms.

Top 10 Celebrity Mention

WORST!KIND Dating Cesspool Stories

here are some hilarious dating stories with hip hop and TV references and the lessons we can learn from them:

  1. The Drake Fanatic

One woman went on a date with a guy who couldn't stop talking about Drake. He quoted his lyrics, played his songs on repeat, and even dressed like him. Lesson learned: While it's perfectly fine to have a favorite artist or musician, obsessing over them on a first date can be a major turn-off. Keep the conversation light and diverse.

  1. The "Breaking Bad" Copycat

One man thought it would be cool to bring his own homemade meth-inspired cocktail to impress his date. Lesson learned: Leave the criminal activities out of your dating life. It's important to know your audience and understand that not everyone shares your interests.

  1. The "Game of Thrones" Obsessive

A man went on a date with a woman who couldn't stop talking about "Game of Thrones." She quoted lines, discussed theories, and even brought her own dragon figurine to the restaurant. Lesson learned: It's important to have a diverse range of interests and keep the conversation balanced. While it's fine to discuss your favorite TV shows, avoid obsessing over them. 

  1. The "Hamilton" Enthusiast

One woman went on a date with a guy who couldn't stop rapping along to the entire "Hamilton" soundtrack. Lesson learned: While it's great to have a passion for something, it's important to be mindful of your surroundings. Not everyone may appreciate a Broadway musical on their first date.

  1. The "Empire" Impersonator

A man dressed up as Lucious Lyon from "Empire" and acted out scenes from the show throughout the entire date. Lesson learned: While it's fine to have a sense of humor, it's important to know your audience and understand what is appropriate for a first date.

  1. The "Jersey Shore" Wannabe

One man went on a date wearing a fake tan, a gelled-up hairstyle, and a "GTL" T-shirt, referencing "Jersey Shore." Lesson learned: Keep it real. While it's great to have a sense of humor, it's important to be yourself and not try to impress your date with a fake persona.

  1. The "Friends" Quoter

A woman went on a date with a guy who wouldn't stop quoting lines from "Friends." He even tried to reenact the famous couch pivot scene in the restaurant. Lesson learned: Keep the references light and don't overdo it. While it's great to share common interests, avoid overdoing the references and ruining the moment.

  1. The "Fresh Prince" Lookalike

One man showed up dressed as the Fresh Prince of Bel-Air, complete with a neon green tracksuit and a gold chain. Lesson learned: Keep the costumes for Halloween. While it's great to have a sense of humor, dressing up for a date can be a bit much.

  1. The "Seinfeld" Fanatic

A woman went on a date with a man who couldn't stop quoting lines from "Seinfeld." He even tried to reenact the Soup Nazi scene in the restaurant. Lesson learned: Keep the references relevant. While it's great to share common interests, avoid overdoing it with dated references.

  1. The "Sopranos" Impressionist 

One man went on a date and tried to impress his date by speaking in a New Jersey accent, trying to imitate Tony Soprano from "The Sopranos." Lesson learned: Keep it classy. While it's great to have a sense of humor, avoid trying too hard and coming across as insensitive or inappropriate.

Top 10 anonymously Mentioned

WORST!KIND Dating Cesspool Stories

The Unwanted Third Wheel

One woman went on a date with a guy she met online. As they sat down to dinner, the guy's mom suddenly appeared and sat down at the table with them. The woman was surprised and confused, but decided to roll with it. The mom proceeded to dominate the conversation and order for her son. Needless to say, there wasn't a second date.

Lesson learned: Make sure to establish clear boundaries with your date and set expectations for who will be present during your date.


The Cat Lady

One woman showed up for a date with a cat in her purse, which was cute at first, but things took a turn when she revealed that she had 10 more cats waiting for her at home.

Lesson learned: While it's perfectly fine to love your pets, it's important to know when your love for them has become excessive. Keep your furry friends in check when you're out on a date.

The Accidental Thief

One guy accidentally stole his date's phone when he picked it up to show her a funny meme. He didn't realize it until the end of the date when she asked for her phone back.

Lesson learned: Always ask before touching someone else's belongings, no matter how innocent your intentions are.

The Ghosting Casanova

A man went on a great date with a woman, but then he disappeared for two weeks. When she finally heard from him again, he apologized and explained that he had been on a romantic getaway with another woman.

Lesson learned: Ghosting is never acceptable, and honesty is always the best policy. If you're not interested in pursuing a relationship, be upfront about it.

The Birthday Surprise

One man showed up to a date with balloons and a cake, only to find out that it wasn't his date's birthday.

Lesson learned: Do your research before planning any surprises. While it's nice to be thoughtful and spontaneous, it's important to make sure you're not overstepping any boundaries.

The Wandering Eye

A woman went on a date with a man who spent the entire evening checking out other women.

Lesson learned: Pay attention to your date and be respectful. It's important to show your date that they have your undivided attention, and nothing is more of a turn-off than someone who can't stay focused.

The Stinky Situation

One woman went on a date with a man who smelled so bad that she had to cut the evening short.

Lesson learned: Take care of your personal hygiene. No one wants to be around someone who smells bad, and it's important to make sure you're presenting your best self.

The Hungry Heartbreaker

A man took a woman to a fancy restaurant, ordered everything on the menu, and then proceeded to ghost her before the check arrived.

Lesson learned: Don't be a jerk. It's important to treat your date with respect and kindness, and if you can't afford to take someone out, don't do it.

The Over-Sharer

One woman went on a date with a man who shared every intimate detail of his life, including his ex's medical history.

Lesson learned: Keep some things private. While it's important to be honest and open, there are certain details that should be kept to yourself.

The Inappropriate Jokester

One man told an offensive joke on a date that left his date feeling uncomfortable and offended.

Lesson learned: Be mindful of your words. What may be funny to you may not be funny to someone else, and it's important to be respectful and considerate of your date's feelings. 

The Surprise Family Dinner

One woman was surprised when her date brought his entire family to their dinner, including his parents, siblings, and grandparents.

Lesson learned: Keep your first few dates private. It's important to get to know someone one-on-one before introducing them to your family.

In conclusion, dating can be a minefield, and sometimes, the experiences we encounter can be both awful and hilarious at the same time. From obsessing over favorite TV shows and musicians to attempting to impress dates with questionable costumes and behaviors, we've all likely experienced cringe-worthy dating moments. However, these experiences can also provide valuable lessons for future dates. It's important to be true to oneself, avoid overdoing references and behaviors, and strive for balance in conversation. Ultimately, a successful date is one where both parties feel comfortable, respected, and able to enjoy each other's company.


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