Dear Jana,
My fiancé just dropped a bombshell. With his bucks party coming up, he’s asked if he can have a ‘free pass’ for the night. Just one last fling before officially becoming a husband.
He swears it’s not about love or emotions, just a one-time hall pass for ‘closure’ on his single life.
Apparently some of his mates did it, and to make it seem fair, he even offered me one in return. Like, ‘go ahead babe, sleep with someone too if it makes you feel better.’
I’m torn. Part of me wonders if this is just typical bloke bravado and it’ll never actually happen… but the other part of me is deeply icked out.
I’ve been nothing but loyal throughout our whole relationship, and the thought of him doing the deed with some random while I’m planning our table settings is making me queasy.
I don’t want to be the boring, uptight fiancée who ‘can’t take a joke,’ but also, I’m not sure my idea of romance includes pre-wedding chlamydia.
Am I being a prude… or is this a massive red flag?
Hall-Pass-Bombshell
A woman asks Jana if she should give her fiancé a hall pass right before their wedding
Dear Hall-Pass-Bombshell,
If this doesn’t prove that the whole ENM (ethically non-monogamous) trend has officially veered off course, then I don’t know what will.
Once upon a time, a buck’s night meant a couple of beers, a strip club, maybe a lap dance if things got wild. Now it’s turning into a ‘last-chance brothel buffet’ and somehow we’re meant to be cool with it? Nope. Not today Satan.
Let’s be very clear here: this isn’t harmless ‘bloke bravado.’ This is a man actively planning to cheat, all under the guise of gift-wrapped language like ‘fairness’ and ‘freedom.’
I mean…. Girl. Offering you a free pass in return isn’t equality, it’s manipulation with a side of guilt trip. Like, congrats sir, you’ve just invented the sleaziest version of feminism. Take a bow, you knob nut.
And sure, technically it’s not cheating… but only because he asked first. That doesn’t make it romantic, respectful, or remotely okay. It’s still deeply icky. Like, ‘congrats on the wedding – here’s a side of STIs’ icky.
Now buckle up, because I’m going to give you the truth straight: he’s craving ‘closure’ from his single life, maybe he’s not actually done being single.
And if you’re standing knee-deep in place cards and floral arrangements while he’s out trying to wrap up his bachelor era with a bang (literally!) I’d say the wedding planning might not be the only thing that needs rethinking.
‘Offering you a free pass in return isn’t equality, it’s manipulation with a side of guilt trip,’ Jana says
Trust your gut on this one. You’re not being a prude. You’re being the sane one in a situation that reeks of red flags.
I’d be booking in a quick pre-wedding counselling, because this one needs to be unpacked with a professional witness who can explain to him just how bonkers his request is.
Dear Jana,
Years ago, I made a mistake that still haunts me.
I slept with my best friend’s husband. It was once, we were both drunk, it never happened again, and we swore it would go to the grave.
At the time, they’d only just started dating, and I convinced myself it didn’t really ‘count’ because things weren’t serious yet.
But fast forward to now and they’re married, they have a kid, and she’s asking me to be her maid of honour at their vow renewal.
I’ve buried the guilt for years, telling myself it was a stupid one-off and there was no point blowing up lives over something that’s long dead and buried.
But the closer I get to standing beside her in that bridesmaid dress, the more I feel like a total fraud.
‘If it was a one-off mistake, never repeated, never even spoken of again, there’s an argument for letting it die with the bad decisions of your twenties,’ Jana says
He’s clearly moved on, and maybe I should too. But what if she ever finds out from someone else? What if he gets drunk and slips up?
She recently told me she’s concerned with his drinking lately, and it made me break out in a nervous rash.
I honestly don’t know what to do. Do I confess and destroy her marriage, or zip it and pray he gets his drinking under control?
Haunted by a One-Night Mistake
Dear Haunted by a One-Night Mistake,
When it comes to cheating, karma rarely misses a beat (that Taylor Swift was really on to something) and by the sounds of it, you’ve been paying the emotional price for years.
You did something selfish – there’s no denying that. You crossed a line. But you also learnt the hard way what betrayal costs. You’ve carried the weight. You’ve lived the guilt. And maybe, just maybe, that’s punishment enough.
But before you fully bury this secret, there’s one last thing to do: you need to have a serious conversation with him. Not a nostalgic trip down memory lane (you keep those clothes on hussy!) Sorry, my anger got a bit passive there.
But seriously, you need to have a sharp, sober warning. If he ever even thinks about spilling the beans after one-too-many beers, you won’t hesitate to walk his wife straight to a divorce lawyer. Lay it out clearly: you’re not protecting him, you’re protecting her.
Because here’s the thing, confessing now won’t undo the past. It’ll just shift the pain. She loses her husband, her best friend, and the version of her relationship she’s been building her life around. And for what? So you don’t feel like a fraud in a bridesmaid dress? Girl, that’s giving slightly narcissistic vibes.
If it was a one-off mistake, never repeated, never even spoken of again, there’s an argument for letting it die with the bad decisions of your twenties.
But your fear around his drinking is valid. A sloppy drunk with a secret is a liability, and the risk of him blurting something out mid-whiskey is real. That’s not just nerves, it’s your gut waving a red flag. So make that warning to him, a serious one.
And in regards to the maid of honour request. You need to buck up, don that frock, and remember this day isn’t about you and your guilt, it’s about your best friend. So you walk her down that aisle with a big ol’ smile on your face. She doesn’t need the details, and you don’t need to unravel under pressure.
You can’t go back and fix it. But you can stop it from causing more damage. That means locking it down, having the hard conversation, and making sure the secret stays buried where it belongs.
You’re not the same person who made that mistake. Don’t let her find out the hard way that he might be.
Dear Jana,
My husband asked me to film a sex tape with him – not just a little phone recording, but full lights, tripod, multiple angles… like a whole production.
I agreed because it felt kind of hot at the time, but now he wants to edit it, add music, and maybe upload it to a private Reddit thread.
He swears it’s anonymous and ‘no one will ever know,’ but I’m panicking. Am I being a killjoy, or is this a major red flag?
We didn’t film our faces, but I still feel like people would know it is us. Help!
Caught on Camera
‘Am I being a killjoy, or is this a major red flag?’ a woman asks Jana about her husband’s sex tape idea
Dear Caught on Camera,
I mean, the tripods and lights probably should have been your first sign this was a bit of a suss situation.
We’ve all got the camera phones out on a particularly saucy night and hit record, but a man that puts in that much effort, isn’t just doing it to add to his wank bank.
But rest assured, you’re not overreacting. There’s a big difference between something feeling sexy in the moment and something being publicly available, even if your faces aren’t shown.
People aren’t as anonymous as they think. A voice, a tattoo, the layout of your bedroom – it doesn’t take much for someone to put two and two together. And the internet really is forever.
So I, personally, think you would be mad to agree to it.
More importantly, this isn’t about whether it’s hot or not. It’s about consent. Just because you agreed to film it doesn’t mean you signed off on it becoming online content.
You’re allowed to change your mind. And if you’re feeling panicked, there’s your answer. It’s a big fat no to uploading it anywhere else. Heck, I would even be asking him to delete it in front of you.
So no, you’re not being a killjoy. You’re setting a boundary. And if he doesn’t respect that, then he’s a walking red flag, and I would be looking at your relationship with a much bigger magnifying glass. Steven Spielberg, this man is not.