Woman Wins The Internet With Most Awkward Threesome Proposal Ever

"And me, not understanding my f**k up yet, laughed and said I was just teasing but we'd certainly really enjoy it."

Image: Vicky Cristina Barcelona

We can all occasionally find ourselves in awkward situations: forgetting someone’s name and continuing to call them by the wrong name until they eventually correct us; going to kiss someone on the cheek, but they move their head and you kiss them on the lips; or walking in on your parents getting down to business.

But have you ever unintentionally propositioned someone with a threesome? That’s exactly what one woman did, and who we now feel comfortably walks away with the award for the most awkward proposition ever.

Posting her horrendous ordeal to Reddit, the woman sets the scene, explaining how she and her husband had hired a babysitter to watch their kids while they both worked from their home office. The couple decided they wanted to start enjoying hitting the town again, post-pandemic, and so they went out for dinner and drinks.

The f**k up happened when they returned home and wanted to continue their night of fun in the bedroom, meaning they’d have to ask their sitter to hang around for a bit longer until their deed was done, “the idea of some *** this evening without the risk of a barge in was very appealing,” the woman relates.

In what could be a good advert to help someone avoid drinking alcohol, the woman – who was a few glasses of wine deep – said to her sitter, “Well… we had been thinking about asking you if you wanted to stay a little longer, we could have sex…”

All she had to do was replace that last ‘we’ with, ‘so my husband and I’, to save everyone from embarrassment. But alas, the brain works in mysterious ways when under the influence, and so what should have been an honest proposal (for more babysitting) turned into a proposition for a threesome.

It got worse – somehow – as the accidentally propositioning woman continued to dig her hole, adding: “And me, not understanding my f**k up yet, laughed and said I was just teasing but we’d certainly really enjoy it, we’d done it with other sitters in the past (lol ugh) but we didn’t make her too uncomfortable and it was completely fine if she wasn’t comfortable with it.”

Eventually, the lightbulb went off in her brain and the realisation of what she’d said came to the fore. But perhaps not in the way you’d expect. It was only when the sitter said: “She would love to any other time, she thinks we’re amazing and it’s such a huge fantasy for her,” that the woman realised exactly what it was she’d (accidentally) asked.

“I start to panic a bit and back pedal saying forget I ever asked, but she doesn’t want me to feel like she’s blowing me off or making excuses. And I’m trying to get out of it but I’m in too deep to say there was a misunderstanding because she’s so into it and supportive and eventually we awkwardly hug and she leaves,” she adds.

Naturally, when she tells her husband, he just laughs (although we wonder if he might have died a little inside since this could have been his chance to bring those ‘online videos’ to life).

The woman then reaches out to the Reddit community for help with what to do in this situation, giving them four options:

A) Pretend like I don’t even remember asking, was too drunk and have no idea what she’s talking about when she tries to bring it up. The coward’s option, potentially mean and childish, but theoretically sparing all of us embarrassment.

B) Explain truthfully what happened, that it was a misunderstanding, and risk making her feel completely embarrassed for being enthusiastically game, and making our relationship with this amazing sitter very awkward. Or she might just have a big laugh over it. The adult option, own your mistakes and clear the air.

C) Ghost her, sell our home and move and change our names. The vacuum cleaner repairman option.

D) Just roll with it and have at threesome with this girl. The heroic option.

The post has quite literally blown up, with thousands of comments from other Reddit users. Some laugh at her situation, some understand how awkward it must have been, but most encourage the woman to take the last option, especially given the fact the sitter seemed up for the idea, just at some other time.

“So does this mean you are going to have to hire ANOTHER babysitter to watch the kids while you all get down with it?”

“Where are they going to find a third babysitter? Well I guess the two babysitters could tag team it.”

“Down south we call that the ol’ Beaumont switch.”

“But then if she gets involved, they’ll need another…..and then….. This is the path to a massive orgy.”

Some suggestions are a little more realistic:

“Maybe the best way is to have hubby talk to girl privately and tell her he’s not into the idea like the wife is, and apologize. “You are beautiful but i wouldnt ever want to risk any kind of rift between my wife and I. But she really trusts you and i hope you will still help us with the kids”

“So everyone saves face, she gets to think they are still attracted to her, they keep the babysitter, and she thinks hubby is really dedicated to his wife”

But most suggested she try option B, but potentially follow-up with option D.

The woman has since updated the post following the responses, sharing, “Thank you all for your encouragement, I’ll be sure to edit an update after I’ve spoken with her. I’ll be going with plan B and potentially leaving the door open for D.”

We await with suspense as to the outcome of the story.

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