Dear Jana,
My newly divorced best friend has just started seeing someone new, and she’s head over heels.
The issue is I used to sleep with him.
It was never serious, just a fling in the early 2000s when we worked at the same big bank.
However, it was definitely more than a one-night stand.
She has no idea. And while I don’t have any lingering feelings for this man – it’s been more than two decades – I feel I should tell her.
My big fear is she finds out from him and thinks of it as a betrayal.
Dilemma.

Dear Dilemma,
I’ll be honest with you – there are few phrases more terrifying to a woman than: ‘I’ve slept with him too.’
But I’ve heard it before, and I’ve said it before.
Because these are the times we’re living in. I learned pretty quickly that once you hit your mid-30s, it becomes surprisingly common to be ‘spit sisters’ with your friends – excuse the gross term – especially if you all live in the same city.
The important thing to note is that you’re not the villain here. It happens.
There’s no denying you have seen your bestie’s new boyfriend’s pecker, and that’s going to cause dramas if it’s not revealed in a timely and sensitive manner.
And it has to come from you, because it would be weird coming from him.
So hike up your big-girl pants and tell her.

And remember, you’re not causing drama; this isn’t betrayal. You’re just covering your bases so this doesn’t spiral into an issue in five years’ time when these two are about to walk down the aisle and suddenly you find yourself blocked from the bridal party WhatsApp group wondering, ‘What did I do wrong?’
We’re all allowed to have a past. But if she finds out later – especially from him – she won’t be mad about the fling. She’ll be hurt that you didn’t say anything.
And, to be honest, it does feel a bit dodgy if you don’t pipe up.
So take a deep breath, pour her a glass of wine, and say: ‘Right, this is awkward, but full disclosure – I had a brief, pants-off moment with Craig in the 2000s. Nothing serious, but I just didn’t want you to hear it from anyone else.’
She’ll laugh. Or wince. Or both. It may be awkward for a while, but she’ll get over it.
And, whatever you do, don’t be overly friendly with him when you all hang out. Your friend will be watching you both like a hawk.
Dear Jana,
My husband and I share a laptop. Recently, while typing in the Chrome search tab, I noticed OnlyFans come up as a previously visited website.
I clicked and discovered an email and password was saved.
My heart sank because I never thought this was something my husband, who is 51, would do behind my back. But I logged in.
He was subscribed to one account. Just one. And she wasn’t a stranger – she was a woman we both knew. The 21-year-old friend of our daughter.
I felt sick to my stomach. The only thing that stopped me from divorcing him on the spot was the knowledge this girl was 18 when she met our daughter at university – thank God. If she had been a friend from school, you bet he’d be out the door.
I haven’t said anything to him yet, but I am devastated. I know he has crossed a line, but so have I by logging into his account.
I understand men watch pornography online, but this feels different.
Should I confront him?
Torn.
Dear Torn,
The problem with male sexual desire is that it often shows up in ways that disgust women.
I lust after older gents with beards, maybe a tattoo or two, and that lived-a-life energy that says, ‘I can build you a bookshelf and make you a dirty martini.’
Men, on the other hand, seem to prefer their women young, perky, and (let me be perfectly blunt here) controllable.
It’s gross, but not illegal. And, if we’re being fair, what a man looks at in his own private time isn’t something we should shame – unless it crosses an obvious line.
Which, in this case, it does.

Because this isn’t just porn. It isn’t anonymous Tits McGee. It’s someone he knows in real life – namely a 21-year-old girl who has met you both in a family situation and probably laughed at your husband’s lame dad jokes.
It’s cringe and inappropriate.
So let’s not dress it up: your husband is being a creepy old man.
He crossed a line the moment he subscribed. You may not know this, but this means she knows he’s watching. (Yes, OnlyFans models can see who subscribes to them.)
So, it’s possible he is doing more than just perving on her photos. He may well want her to know that he is watching.
If this is the case, then we are talking about more than just harmless, occasional porn consumption.
You absolutely should confront him. Tell him to unsubscribe or your marriage is over – giving him all the time in the world to message girls on OnlyFans.
Dear Jana,
A few weeks ago, I had ‘the talk’ with my new boyfriend about him staying in touch with exes and old Hinge matches.
He was still friends with them on Facebook and followed them on Instagram, which is fine, but I wasn’t comfortable with the messages, comments and story replies.
It felt like he was talking to them literally every day, even in my presence.
His friendships are his business, but it felt to me like he was keeping one foot in his old single life.
So he agreed to stop the messages and comments, and everything seemed to be back to normal.
Then I discovered he was still in touch with them on Strava. It’s a running app for fitness types that he knows I don’t use and I only cottoned on to what he was doing because I saw email alerts on his phone when one of these girls replied to him.
I feel betrayed. I asked him to stop and he’s still doing it, hoping he won’t get caught. What should I do?
Running from Commitment.
Dear Running from Commitment,
You’re both in the wrong here.
You’re giving off controlling and he’s giving off ‘don’t tell me what to do’ – admittedly in a passive way.
The fact that you know who his exes are, and how he communicates with them, tells me you have turned into a super sleuth, tracking his every move. That’s not healthy.
It’s taking up far too much energy that you could be using elsewhere – like your career or the bedroom.
A male friend recently told me his girlfriend goes through his Instagram and demands to know how he knows each woman he follows. I could think was ‘red flag’.
And you are giving the same kind of energy.
In a secure relationship, you wouldn’t feel the need to do that. So ask yourself – is this coming from baggage you’re still lugging around from past relationships, or is it because, deep down, you know he’s up to something?
Figure out which one, because that’s your starting point.
Psychologically, when you tell someone they can’t have something, their brain starts obsessing over it. It’s the same reason we all want to cut carbs until someone mentions garlic bread, and then all we can think about is garlic bread.
You told him to stop messaging girls and all of a sudden he found a crafty way around it. I wonder what would have happened if you simply didn’t react or put hard and fast rules in place?
But here’s where he loses me: he knew what you meant. He agreed to stop. And instead of being upfront or negotiating a boundary that worked for both of you, he just shifted the behaviour to a new platform.
That’s telling. So perhaps your spidey senses were on to something.
To me, it appears he’s passive-aggressively fighting a rule you put in place, rather than just telling you ‘No, I get to choose who I stay friends with, not you.’
But on the flip side, it also could be proof he’s not ready to close the door to his single life fully. He clearly likes the idea of being in a relationship, but he also likes keeping a fan club on standby.
It’s a dopamine hit and an ego boost. That tiny thrill of knowing someone out there still thinks he’s hot in bike shorts.
So, yes, you helped create this dynamic by trying to police his inbox. But he escalated it by lying through omission.
Tell him you’re not interested in being the social media police. Either he wants to be in the relationship fully, or he wants to keep one foot in his single life.
He can’t have both.
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