Six Ridiculous and Cringeworthy Reality Dating Shows from the Early 2000’s

Reality shows are commonplace on TV today, with popular titles such as Survivor, Big Brother, and 90 Day Fiance; but before these familiar shows were the ones that started it all. The awkward and unexpected moments had viewers glued to their televisions and some were even too cringe to watch.

Brian and I are pretty big into Twitch and one of our favorite streamers Hasan Piker recently began watching a forgotten dating reality show from the early 2000s. Now, I had never heard of this particular program, but it was so fun watching on Hasan’s stream that I found myself diving deeper into the rabbit hole of reality tv shows. I had absolutely no idea that many even existed. Literally hundreds, in a plethora of genres. For time’s sake (and sanity), I am going to stick to dating shows in the early 2000s that aired for only one season and are US-based. Here is my list of the most ridiculous and cringe-worthy:

1. Playing It Straight (2004)– This is the show Hasan streamed and hoo boy- I am surprised there weren’t more shocking moments, but for 2004, it was actually pretty tame. A midwestern woman named Jackie and 10 men spend a week at a ranch trying to make a love connection. The twist? Some of the men are gay, and some are straight. No one knows who is who, including the other contestants. If Jackie picks a straight man, she and him split a million dollars. If she picks a gay man? He walks away with the entire million and Jackie walks away with nothing but a broken heart.

2. Boy Meets Boy (2003)– Similar to Playing It Straight, BMB features a gay man in search of his Mr. Right, unaware that the 15 potential suitors are a mix of both gay and straight. However, neither leading man James nor the gay “mates” (as they are called) are ever informed until near the end of the show.

3. Mr. Personality (2003)– I actually kind of like this idea, but the execution definitely leaves something to be desired: A single woman must choose from 20 men solely on their personality. Each male is disguised by wearing a mask throughout the entire dating process. Hosted by… Monica Lewinsky (if that doesn’t scream early 2000s, I’m not sure what does!).

4. My Big, Fat, Obnoxious Fiance (2004)– I actually loved this one! I viewed it as it aired and couldn’t wait to see what happened each week. Beautiful and sophisticated Randi meets not-so-Prince-Charming Steve and has to convince her family and friends they are in love and will be getting married. If she can make it through the final “I Do’s”, Randi and Steve will split a million dollars. The twist? Steve is actually a paid actor and is in on the extravagant prank, leaving Randi with the entire million if she wins.

5. Chains of Love (2001)– More of a game show, Chains of Love had rotating contestants each week. One person (the “Picker) agrees to chain themselves to four members of the opposite sex for four consecutive days and nights hoping to find true love. The Picker is given $10,000 and can give a portion to each person eliminated or choose to keep it for themselves. How was this ever thought to be a good idea??

6. Dismissed (2001)– This sounds both horrible and entertaining. Another game show format, one person simultaneously takes two people of the opposite sex on a date and can eliminate their least liked at any time. The two suitors also have “time out” cards which, when used, give them 20 minutes alone with their date.

Honorable mentions:
1. Who Wants to Be a Princess (2001, UK)– While it may actually classify as a game show, this 2-hour special showcased thirty women competing for the attention of a European prince who’s identity would only be revealed at the end of the show. What did the lucky gal win? A necklace worth $40,000. Sounds like the better option to me!

2. There’s Something About Miriam (2003, UK)– Six men strive to be the object of model Miriam’s affection to win her heart and 10,000 BP. Unbeknownst to them, Miriam was a transsexual whose gender was not revealed until the final episode of the show. This led to a string of lawsuits and one of the contestants later being featured on Phil Collins’ installation of “people who believe their lives have been ruined by appearing on reality tv”. Sadly, Miriam was found deceased in her apartment in 2019.

Have you seen any of these dating shows? Or would you watch them? What shows do you feel should have made the list? Let me know in the comments below!

By Raven Alford

Raven has been a product tester and reviewer for 15+ years, working with invite-only programs (such as Amazon Vine and Highlight) and premium brands. Micro-influencer and wannabe foodie, Raven enjoys a variety of topics and interests, and loves bringing them to the public. A true child of the 80's & 90's, she loves old school gaming and fashion; and her favorite band will always be New Kids on the Block.

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