The Most Uncomfortable Dating Naked Moments

Ah, dating. Everyone has at least one story of an incredibly uncomfortable moment they couldn't wait to escape. But we're guessing none of them compete with VH1's Dating Naked, which aired for three seasons from 2014 to 2016. The premise was a relatively simple play on similar reality dating shows: One male and one female contestant remove literally all of their inhibitions before going on a few dates with each other and two other suitors — while completely nude. Of course, there was also a "selection ceremony" in which each contestant either chose each other or their respective dates. Think The Bachelor but in the buff. Just how weird did things get? "Multiply any 'first' you've ever had by about 1,000 to get anywhere close," Entertainment Weekly wrote.

The series burned out quickly because it made more of a splash through hype and controversy than actual viewers. But despite the show's seemingly shallow premise, it actually attempted to explore loftier concepts. In an increasingly digital world, there was something raw and real about baring it all and wearing one's heart on one's sleeve — well, if actual sleeves had been allowed. As a former contestant Mike put it (via Us Weekly): "As long as you're comfortable with yourself and in your own skin, the rest is just clothes." That's deep, Mike.

Do you recall your most uncomfortable moment on a date? At least it wasn't televised, right? Get ready to cringe because here are the most uncomfortable Dating Naked moments.

A Dating Naked deja vu

In Season 1, Episode 9 — the audience met Juliet, a British dance instructor, and her mystery date, Cole. Well, not so fast. As soon as he walked up — totally naked, of course — she greeted him with a mixture of laughter and underlying dread. Awkward — the two had met before. Us Weekly recapped the moment. "I've actually worked with Cole before on a job," she admitted, adding, "Obviously, I don't know him this well." 

After the awkward reunion of sorts, the couple went on a canoe ride with only one major splinter incident. When Juliet and Cole made it to dry land the two bounced on a trampoline together with no support in sight. The couple didn't hate each other, which is as much as one can hope for in this scenario. So, Juliet invited Cole back to the villa. He decided to drink too much but delivered the sweet line, "Seeing you ignited my heart." How cute! However, he followed it with, "You've got great t**s." As Us Weekly summarized, when Cole "finally tries to pop a pimple on her cheek, Juliet officially calls it a (disappointing) night."

Surprisingly, Cole's clumsy grooming attempt didn't completely blow it for him, as Juliet ended up choosing him in the selection ceremony. But they did save a little cringe for last with this update on how things went post-show: "They've confirmed that friends can be lovers ... many times over."   

A not-so-magical first date

By the time he reached Season 2, Episode 3, main man Chris was basically a professional naked dater, which is probably not a title you'd leave on a resume. Anyway, on the beach, fully exposed, he saw his date walk up sporting an article of clothing, which doesn't seem fair. Well, to make things as weird as possible, she was completely naked except for a rubber unicorn mask. This was  how he met Mariah from Las Vegas — who also owns a ferret. Chris wasn't that interested, partially because his heart was still with previous women he naked-dated, but the date carried on and the two went on a terrifying water adventure. Mariah and Chris cozied up next to each other on a coach — an inflatable raft version pulled through the water at lightning speed.

Back at the villa, Chris returns to his favorite ladies but Mariah — a true party girl — decides to have some fun. First, she shows off her musical side by playing a pair of bongos with her boobs, The Cut recapped. At this point she had no shot but continued to let loose. The others ignored her and eventually Chris finally put the wacky Mariah to bed.

An intense naked date ends with a black eye

There's a lot of swinging in Dating Naked, between different people and different body parts. In Season 1, Episode 3 — macho man Keegan meets his date Katie. Their adventure for the day? Ziplining. It didn't take long for Keegan to be turned off by Katie, and for him, strapping in together sounded like a terrible idea. "I didn't want to have any physical contact with her because she kind of repulsed me," he said, according to International Business Time's recap. Despite the feeling, Keegan and Katie rode in tandem. It was a picturesque glide through the treetops, which seemed to help. That is, until one of them forgot "to pull the handbrake and Katie's face slams into the stopping block," per The Cut

Then back at the villa, Katie was out for blood against Keegan. She placed all the blame for her black eye on Keegan for allegedly causing her accident. Her revenge consisted of getting drunk and then making out with another guy at the house, Scott. As VH1 recounted, he "quickly came to his senses and bailed on her." And his reason was simple but justified. "She's just crazy," Scott said. He eventually ditched Katie, leaving her alone at the pool. She then proceeded to ask the production crew to take a naked dip with her. There was no audible response, but when camera started rapidly panning back and forth from left-to-right, that seemed like a definitive "NO." Yikes. 

Dating Naked stirred this contestant's vibrations — no, not those kind

In Season 1, Episode 8 — the young and beautiful Moenay pushed aside her fear and decided to give naked dating a shot. Sure, personality is important but she probably would have appreciated some eye candy close to her own age, too. Well, she got Dan — a 42-year-old life coach. According to Us Weekly's episode recap, Dan had "the looks of an aged Abercrombie model," but he and Moenay were not on the same frequency — literally, thanks to his "odd habit of discussing vibrations and shifts in energy" on the planet. Their paddleboarding excursion couldn't end quickly enough. "He's giving me these weird stares like he's trying to steal my soul," Moenay confessed to the camera, adding, "My date's weird."

Naturally, "old man Dan," as he has perhaps cruelly came to be known, made it back to the villa amongst the other much younger contestants. Talking to anyone who would listen — so, nobody — he explained "how to harness the planet's frequency from within." Totally fed up with the scenario, Moenay admitted it in a confessional segment that made more sense to rest up for her third date than "waste any more time with Dan." With that, she took a final gulp of wine and went to bed. 

Left standing with absolutely nothing, not even clothes

Moenay got more than she could bargain for with "old man Dan" — her second date on Season 1, Episode 8. He spent most of the date giving creepy eyes and talking about the planet's frequencies. Interesting for some, frightening for Moenay. After the frustrating date, at least she could move on with a new man for her third date. Sadly, the bad luck continued. The mystery man got a case of stage fright and bailed seconds before undressing. "My mother said, 'If you do this you'll embarrass us all,' and I just can't," he confessed to a producer, via Us Weekly.

Once Moenay learned her date totally ditched, she began to cry. Clearly frustrated for working up all the courage to even participate in such an experimental show, she said "I just feel robbed. "It's heartbreaking. I feel like it was another failure," she added. It was a tough moment but perhaps worst of all, her reward was to return to life coach Dan.

Was is possible to have too much fun on Dating Naked?

Most people try to bring out their best attributes on a first date, whether it's a joke, magic trick, or just a genuine smile. Dating Naked gave the world a whole range of first date flexes, from the delightful to the truly uncomfortable. Contestant Vinny lies on the latter part of the scale. In the first episode of Season 3, he paired up with Natalie for a game of soccer. Nothing spectacular happened until the pair made their way to the villa.

Poolside, it was Vinny's time to shine in front of the other nude daters. For his best move, "he tucked his ... package between his legs for all to see," Us Weekly recalled. He wasn't done. "That's what you call the man-gina, and then you go like that, and that's a fruit basket," Vinny over explained (via VH1). Obviously, this impressed no one. Later, poor Natalie spoke for herself — and presumably the audience — when she exclaimed, "'Oh, my God, I want to die,' as Vinny was shown peeing into the ocean." For a night cap, sweet Natalie kindly showed drunk Vinny to his room. Before she left, he declared, "I love you!" Her reply? "Alright." Ouch.

The next day, Natalie sent Vinny home but he had to get in one more line — "I mean, if she can't handle what I do in the streets, she ain't going to like what I do in the sheets."

Who breaks up at a wedding?

Dating Naked producers' dreams came true when two contestants fell in love and decided to get married. You know what that means — a season finale wedding episode. In the last episode of the first season, Ashley and Alika held their nuptials in southern California. And, of course, the dress code was in fact no dress at all — a naked wedding. The couple invited back many of the Season 1 favorites so the audience had a chance to catch up. At the start of the episode, joker Steven confessed he and previous date Marissa were "in the 'early days' of their relationship" and still "working things out," via Us Weekly.

Later in the episode, Marissa shared her side of the story. She "had enough of Steven's antics." Even Steven seemed completely over her attitude towards him. "She's more of a mother than a girlfriend," he admitted. Heading towards doom, the couple left the reception for a classic we-need-to-talk scenario. Steven said, "I think you and I are better off as friends, clearly." Marissa agreed, and while the pair split ways, at least the main couple had a special day to remember.

Congratulations Keegan, you're a reality TV pioneer!

Big and buff Keegan flexed his muscles several times during Season 1, Episode 3. On his second date, he paired up with "the overly confident Jesse," as she was described in The Cut's recap. Things quickly turned dirty during the pair's spa date. Keegan and Jesse rubbed mud all over each other and wrestled in the sand, which clearly made the big guy happy in every sense of the word. Yes, we're talking exactly about the inevitable way you think we mean that in the context of a naked wresting match, which The Cut also deemed was a first for the racy show. Jess didn't miss it — after all, how could she? "Maybe at one point, Keegan might have gotten a little bigger," she revealed, via PopSugar. But she also confessed, "I would like to think I would have something to do with it." Awe? Ew? You decide. 

Back at the villa, the two weathered the human tornado that was Katie. She got a black eye from a zip lining accident on her date with Keegan that day, and she was clearly out for revenge. She got intoxicated and made out with another guy, so the results the next day came as no surprise. Keegan passed on Katie and picked Jesse during the selection ceremony. Katie's response was a final cringefest for the episode: a profanity-laced takedown of her fellow contestants, the crew, and the network that stages the show. 

Dating Naked found 'the most un-sexy thing you could do on a date'

It may come as a surprise that a contestant on a show called Dating Naked was a virgin, given the revealing nature of the premise. But in Season 1, Episode 6, the world met Angelica — a very appropriate name for the scenario. "The New York native revealed that although she was a virgin she originally thought the idea of Dating Naked didn't seem so scandalous," International Business Times recapped. But when it came time to bare it all, she had a case of stage fright. Producers luckily convinced her to carry on and Angelica met her naked date Greg, which caused a whole new set of problems. Upon seeing Greg in all his glory, Angelica "let out one heck of a screech," because it was her first time seeing a man's member in real life. Apparently, the warning from her friends that "it could be a little scary" fell short of reality. 

Though she pushed through her fear to appear on the date, things quickly went downhill once the adventure started. The pair enjoyed a lovely boat ride until Angelica started feeling sick. She had to spin her head overboard for "the most un-sexy thing you could do a date," VH1 summarized. Angelica had enough of the entire experience and promptly left the show.

This Dating Naked contestant somehow crossed a boundary line

A regular date is scary enough, so imagine being completely exposed. While most contestants on Dating Naked started off a bit nervous, eventually tensions eased up. Then there are folks like Frankie. This man strutted out with confidence on Season 2, Episode 3 for his date with Kerri. He seemed completely in his element. Kerri recognized his attractive physical features and attempted to help him gently into the bizarre premise. But Frankie needed no help at all. In fact, he showed his fearlessness by swinging and flapping his ... personality all around. For their date, the two got up close and personal with massages. While Frankie was on top, he shared "nuggets of wisdom like: 'You ain't learnin', you ain't livin' and 'To advance, take away the pants,'" The Cut recapped.

Frankie made it back to the villa and into the following morning for the selection ceremony. Unsurprisingly, he kept to his swinging ways and host Amy Paffrath even called him out. "Frankie, we've had enough of that," she said. Kerri also had enough of that and sent Frankie packing.

Downward dog into upward attraction

In Season 1, Episode 4 — the lovely Camille blushed when she first locked eyes with Julian and his tattoos. Plus, she noticed that he walked into the situation fully prepared prepared for anything. Well, just one thing, actually. The two set out for a calming yoga date. But he missed the memo to breathe and relax. Camille's poses were apparently too hot for Julian to handle and he found himself aroused, again, which in fairness to the guy wasn't exactly the easiest situation to navigate. 

Luckily, Julian addressed the uncomfortable scenario in real time, telling Camille, "I'm sorry I'm getting excited." He elaborated later in a confessional, bluntly stating, "I just could not help it. Naked women do turn me on." You don't say! Camille didn't have the same positivity as her partner. "This date is incredibly awkward. I have a d**k in my face," she said. "I'm not into this yoga." Neither was the audience, we imagine. Killing any remaining ounce of hope, Julian proceeded to talk about his love of sci-fi and aliens. This couple wouldn't work even on another planet.

This Dating Naked contestant pumped himself up

First dates can seem a bit like a job interview when explaining, "What do you do for a living?" On Dating Naked, one contestant had a shocking answer. In Season 2, Episode 9 — Kerri already fell for several impressive dudes. But with one episode until the finale, perhaps gold would strike with another perfect bachelor. Her first date Chase explained he sold medical equipment. Was this prince charming a doctor? Nope. He sold male enhancement machinery. "He very sweetly tells Kerri how he changes people's lives with his penis pumps and fixes relationships," The Cut summarized. Despite his interesting profession, Kerri admired Chase's kindness and decided to keep him around.

The rest of the crew got to meet Chase back at the villa — always a spot for excitement. In a demonstration that no one asked for, he brought out his product "for a demo." As fellow contestant Chris said, "It's kind of like one of those things that you don't want to look — but you can't look away." Kerri ultimately looked the other way and sent Chase home.