Dear Jana,
I’m fresh out of a divorce and dating this incredible guy, but he turns into a detective on steroids whenever my past comes up.
On our second date, he asked how many people I’d slept with.
When I laughed it off, he kept pressing, saying things like, ‘Give me a ballpark figure? Was it more than 10? Twenty?’
That was followed by a string of questions: Have I ever had a threesome? Dated a married man? Would any of my exes call me ‘crazy’?
He even asked to see old photos so he could ‘put faces to names’.
It’s starting to feel less like a date and more like an interrogation. I really like him, but is this just curiosity or a massive red flag?
Third Degree.
A divorced woman asks Jana if her new man is a ‘red flag’ (stock image posed by models)
Dear Third Degree,
Firstly, congratulations on making it out the other side of a divorce with enough energy left to go on dates. That’s no small feat.
Now, to the topic at hand… Red flag, red flag!
His, er, ‘archival enthusiasm’ about your sexual past isn’t healthy curiosity. It’s not a playful ‘tell me about your wild twenties’ over a glass of wine.
It’s a test. This kind of obsessive digging isn’t about you – it’s part of a toxic subculture that’s taken root in the darker corners of the internet: the manosphere.
Men who’ve been marinating in that world tend to see women as a set of statistics to be graded: sexual history, ‘body count’ (yuck), whether you’ve ever made mistakes.
This is not curiosity – it’s control dressed up as conversation. Like I said, red flag.
And while you might really like him, the issue is this: people who start relationships trying to ‘audit’ your past often end up policing your present. Today it’s how many people you’ve slept with. Tomorrow it’s why you wore that dress, why you’re meeting that male colleague for coffee, why you didn’t text back in two minutes.
‘On our second date, he asked how many people I’d slept with.’ (Stock image posed by models)
My advice is to answer his questions with the same grace you’d offer a stranger on the train who asked about your underwear: none at all.
You are allowed to keep some things just for yourself.
You’re also allowed to decide whether someone who is this fixated on your sexual history is going to be the kind of partner who makes you feel safe and loved.
The right man won’t care about your number. He’ll be more interested in the woman who turned up at date No. 1 post-divorce, resilient and brave enough to try again.
Find a man who adores you, not controls or judges you. They are out there, I promise.
Dear Jana,
I think I might be addicted to sex.
Honestly, it sounds ridiculous even as I type this, but hear me out. I’m 32, single, and my life revolves around dating apps, hook-ups and sexting.
I’ll sneak off to the work bathroom to swipe through Tinder, and I once left a friend’s birthday dinner early because a guy asked me if I was available for sex.
The next morning, I woke up to discover I’d been kicked out of our friendship group chat for ditching the party. Apparently vanishing mid-speech to hook up is ‘peak selfish behaviour’.
I’ve even lied to dates about being ‘exclusive’ just to keep things ticking along with my regular roster of men.
I’m exhausted, but also fear getting bored if I slow down and commit to one man. Is there something wrong with me, or are other women like this too?
Sexually Spiralling
‘I’m 32, single, and my life revolves around dating apps, hook-ups and sexting’ (stock image)
Dear Sexually Spiralling,
There’s nothing inherently wrong with wanting a lot of sex, or indeed rearranging your plans to have sex.
It’s one of life’s great pleasures, and if you’ve been enjoying it, good for you.
But there’s a difference between enjoying something and having it rule your life. What you’re describing sounds like compulsion, not desire.
Choosing a stranger’s sheets over your oldest friend’s birthday, then waking up to a flurry of furious texts isn’t great – but you know that already.
May I suggest this isn’t about the sex itself, and more a self-esteem issue?
Rushing to a man’s bed when you could just as easily have seen him another time – or, even better, enjoyed a superior orgasm on your own – suggests you’re craving male attention.
I’d dig deeper into why you feel you need it.
That’s your first red flag. The second is lying.
It is unfair to lie to men that you’re exclusively dating when you aren’t. Bailing on your friends is also lying – if you promised to show up and didn’t.
But I suspect your lies aren’t really about sex. They’re about topping up your habit without pesky interruptions – like friendships or men who might be falling for you.
And you keep this habit because you fear boredom. But here’s the thing – ‘boredom’ isn’t the enemy.
Think of it as a pause – a bit of space that lets you figure out who you are when you’re not chasing the next dopamine hit. It’s in this space that you call ‘boredom’ where richer things can grow. Deeper friendships, more satisfying relationships, and yes, better sex.
My advice is to take a week off the apps and fill your time with people and experiences you can’t swipe for – dinners, books, long walks with your phone tucked away.
Notice how you’re feeling. If the panic of not being able to engage in your usual behaviour feels unbearable, it might be time to speak to a therapist.
Dear Jana,
I’ll get straight to the point: the make-up sex with my boyfriend is so good, I’ve started picking fights with him on purpose.
The problem is, those fights can get nasty. We’ll drag up old arguments, throw in a few personal digs and end up in icy silence before jumping into bed.
It’s exhausting and confusing. How do we break the cycle and learn to argue without turning it into foreplay?
Firestarter.
Dear Firestarter,
There’s a reason make-up sex feels so intoxicating. Biologically, your body rides the adrenaline and cortisol from the argument straight into a hit of oxytocin and dopamine from sex. I once had an ex-boyfriend who looked irresistible when he was angry, so I get it. It’s primal.
But it’s essentially an emotional cocktail – fight, then reconcile – and it’s addictive. Plus, all that cortisol can leave you with a puffy face. And nobody wants that.
Here’s the real issue: it’s not intimacy you’re chasing, it’s drama. And while drama can feel like passion, it’s just a knock-off version. It’s like reaching for a McDonald’s burger when you’re starving – you’ll feel full for a moment, but it doesn’t nourish you.
What you’re building isn’t just a habit, it’s a pattern.
If conflict becomes your foreplay, you’ll invite it more and more. And every time you fling an old argument back into the ring to chase that post-fight high, you chip away at the trust that makes the sex worth having in the first place.
If you want the chemistry without the carnage, try generating it outside the battle. Flirt more. Surprise each other. Go watch him play some sporty thing. Have sex when you’re in a good mood, not just when you’re half-furious.
And, for God’s sake, when you do argue, keep it about the matter at hand – not every grievance since 2019.
Healthy relationships aren’t ones where you have to burn the house down to feel the heat. They’re the ones where the warmth is always there – no fire-starting required.
