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March 21, 2024 By Cosmo

5 Funny Worst Date Stories from Boomers’ Favorite Sitcom Characters

funny worst date stories from the boomers favorite sitcom characters

The more you date, the better your odds at having a few dating horror stories. Take heart. It’s not a reflection on you or your character. Your worst date tales may even become treasured memories, over time.

Bad dates are simply part of the mature dating process.

Remember that every “no” is one step closer to a “yes!” Finding a compatible partner in love takes time, patience, and a little work.

If you’ve recently had an awful dating experience, share it with a friend. Vent a little and move on to the next one.

Laugh about it. Sometimes a little laughter will lighten your load. A good laugh is restorative.

If you don’t believe me, take a few minutes to check out these funny worst date stories from some of boomers’ favorite TV sitcom characters of the 70’s, 80’s and 90’s. Even if you don’t have any horrible date stories, you might like a laugh anyway!

With so many streaming services available, offering so many of our favorite long-ago TV sitcoms, it’s easy to revisit them just about any time we’d like.

Daisy and I often go back to re-watch our all-time favorite shows, some of which are noted below.

Everybody Loves Raymond: Robert Thinks She’s “The One”

This excerpt from Everybody Loves Raymond shows Robert Barone (Ray’s brother) proudly introducing his new love to the family. He thinks he’s found “the one.”

As many of us have found in our dating experiences, even the best-looking exterior can hide some disturbing character traits.

Frasier: Niles’ Worst Date (“Oh my God, I’m Dating a Whore!”)

The intelligent and bookish Niles is pleased as punch with his newfound girlfriend. She dresses beautifully and treats him like a king. She listens intently, even when he’s prattling on about one or the other of his collections of strange artifacts.

It takes strong words from his brother, Frasier, to get Niles to see that which is obvious to everyone else.

Golden Girls: When Every Man is “The One”

Rue McClanahan played southern belle Blanche on the Golden Girls.

On her insatiable appetite for dating one man after another, Blanche remarks, “My body feels like a Corvette up on blocks with its engine racing…the wheels just spinning, with nowhere to go!”

It was never long between the end of one first date and the start of the next one. Serial dating at its finest.

Seinfeld: When You Date Someone for All the Wrong Reasons

A key element to truly mature dating is that you go into it with good motives. Proper motivation gives you a fighting chance at finding your true love. I don’t think any character on Seinfeld ever dated anyone without at least one ulterior motive.

Here’s a good example of what happens when you date for all the wrong reasons.

In this case, Jerry’s good friend George Costanza has a date with the daughter of the woman who is his unemployment officer, in an attempt to keep her from cutting off his benefits. He’s not at all attracted to the daughter. In fact, he’s kind of repulsed by her. The date goes terribly wrong and, naturally, he ticks off his date’s mother.

All in the Family: When Your Family Has Something to Say About Your Dating Choices

What counts as a horrible date story? It depends on your perspective.

In this video, Archie and Edith’s niece Linda is dating Lionel. Linda and Lionel are a happy interracial couple. That should be the end of the story.

The lovers’ two bigoted uncles see things differently.

If you like this article, please share it with others using the social buttons.

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Filed Under: Second Dates and Beyond, Sex and Romantic Relationships, Single Men Over 60

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