A woman, wearing a leopard print hat, smiling and winking

Episode 3 Roleplay Dan

February 23, 20265 min read

Whisks, Wine & Weird Men: Episode 3

After a traumatic break up 7 years earlier, I eventually found myself edging towards 50 and thinking...

Right.

I don't even know what I want anymore.

I didn't feel ready to properly date.

But it had been... a while.

Long enough that I wasn't entirely sure I still knew what I was doing.

I was terrified.

After so long, it felt like I'd misplaced that version of myself somewhere between motherhood, back pain and cake batters.

So, in. a moment of bravery (or madness) I thought:

Maybe I just need to get my confidence back.

Enter..

Dan.

Plenty of Fish.... The Swamp Within The Swamp

I met Dan on a dating app called Plenty of Fish.

Plenty of Fish is not a dating app.

It is scraping the bottom of the barrel with a teaspoon.

Full of men who have adapted beautifully to the swamp.

Men who make you understand why women choose to live with cats.

Roleplay Dan

Dan was 39....

Or at least.... he said he was...and somehow, over the year and a half we stayed in touch, he remained 39 the entire time.

And he loved the fact I was 49.

He made a huge deal of it. 

He was flirty, confident, cheeky...

And he wanted to meet up.

But before we met, Dan asked if I fancied a bit of role-play .

Now, I had no experience of this.

None.

I was barely emotionally prepared to choose a nice outfit, let alone become a character in whatever drama Dan had planned.

"Oh don't worry.... I can teach you."

Which is always a reassuring sentence to hear from a man on plenty of fish.

The Landlady & The Handyman

Dan's fantasy?

He wanted to be dominated by a strong, often aggressive woman.

Landlady vibes.

A landlady who needed a handyman vibes.

I'm not even joking.

I remember thinking:

Hold on...

I'm just trying to regain confidence and now I'm being cast as an aggressive landlady with a plumbing issue?

This is not dating.

This is GCSE Drama.

And the funniest part?

If you knew me in real life, you'd know I'm about as aggressive as a Victoria sponge.

I'm calm, sweet natured, I'm chilled.

I'm the type of woman who apologises when someone bumps into me.

So the idea of me strutting around like some terrifying dominatrix landlady was.... quite frankly ridiculous.

Text Role play (Yes Really)

We started roleplaying by text.

Which ... now that I am writing it down...

is actually quite weird.

It felt like I was doing improv acting in my kitchen while making a cup of tea.

But I'll admit, it was entertaining for a while.

And in some strange way it did give me a bit of confidence back.

The Real Life Roleplay Ambush

A week or so later, Dan arranged to come to mine.

Empty house.

Question decision making.

The night before he messaged to confirm he'd really like to "do the role play properly."

Properly.

Because I am not, by nature, a theatrical woman.

and now I'm expected to perform live as an aggressive landlady?

What do you even wear for that?

A blazer?

Heels?

A whip?

A cardigan?

I had no idea.

What Actually Happened

Turns out I am not built for scripted seduction..

I panic under performance pressure.

So we abandoned the theatrics

No accents.

No fake scenarios.

No method acting required.

And once nobody was pretending to be anybody else...

It was actually very good.

Not romantic.

Not life changing.

Just reassuring.

Forever 39

Dan Drifted in and out for a while.

The odd message.

The occasional attempt at theatrical texting.

But if I'm honest..

It got dull.

And the longer it went on, the more I thought:

What am I entertaining this for?

He also had a strange sense of humour.

Sometimes funny.

Sometimes sharp.

Sometimes just... unnecessary.

And then, predictably, he ended up back with his wife.

Which surprised absolutely nobody.

Least of all me.

Petrol Money?!

Then one day, out of the blue, he popped up again.

Apologising for not being in touch...

because apparently he'd "lost all his numbers"

Sure.

And then he said (in what he claimed was humour)

"If you pay my petrol money, I'll come over and do what ever you want."

"You want petrol money?"

Pause.

"I'm sorry... what?"

He tried to persuade me.

Naturally.

And then, as if this improved matters, he added:

"Oh by the way, I have a girlfriend now and it's going really well."

Right.

Well I'm sure she'd be delighted to know you're crowdfunding petrol money for extracurricular activities.

Blocked.

The Plot Twist

And then....

last year...

I received an email through my website.

An organic enquiry.

From Dan.

Because apparently blocking someone on your phone does not prevent you from googling them.

"Hey just an old friend saying hello."

Signed off:

Forever 39

Old friend.

We shared petrol negotiations and mild delusions.

He signed off like nothing had happened.

Like girlfriends, role-play and crowdfunding were minor footnotes.

As if time had simply paused for him.

And that's when it hit me.

Dan is forever 39.

Not in age.

In behaviour.

He doesn't move on.

He just rotates.

Because modern dating is a perfect ecosystem for men like Dan.

Low effort.

Infinite access.

Endless women.

Why grow... when you can just reappear?

I, however, had evolved.

Blocked.

Welcome to the swamp.🐸

Sasha, affectionatly known as the Meringue Queen, is a passionate baker, barista, and digital baking instructor based in the UK. With decades of experience, she's known for her creative flair, signature mocha tarts, and legendary bread and butter pudding. Sasha inspires home bakers with her mindful approach to baking and her belief that every cake tells a story. When she's not crafting stunning bakes, she's spending time with her dog Tiffin or working on her next digital masterclass.

sasha jenner

Sasha, affectionatly known as the Meringue Queen, is a passionate baker, barista, and digital baking instructor based in the UK. With decades of experience, she's known for her creative flair, signature mocha tarts, and legendary bread and butter pudding. Sasha inspires home bakers with her mindful approach to baking and her belief that every cake tells a story. When she's not crafting stunning bakes, she's spending time with her dog Tiffin or working on her next digital masterclass.

Back to Blog