My Whore Era Has Rules: How I Keep It Fun Without Losing Myself

I realised I needed rules on a night bus.

Very glamorous. Very cinematic. Me, slightly overdressed, holding a meal deal I had absolutely no business buying at that hour, pretending I was casually fine while my brain opened seventeen tabs at once.

I had been on a date. It was fun. He was funny. I liked the way he looked at me, which is an embarrassing sentence to type but there we are. I also liked that I had left when I wanted to leave.

Not dramatically. Not because anything awful happened. Just because I noticed myself starting to do that old thing where I become agreeable as a survival skill.

You know the one.

The one where “I’m easy” really means “I am hoping you will like me more if I have no preferences.”

Reader, I am trying to retire her.

My so called whore era started as a joke in the group chat. It became a shorthand for dating, flirting, saying yes to more of what I actually wanted, and letting myself be curious after years of trying to be sensible in a way that quietly shrank me.

But the more I dated, the more I realised something important.

Fun without boundaries is not freedom. It is admin with better lighting.

Anyway. Growth finds us in strange places.

What I Mean By Whore Era

Let me be very clear, because the internet loves taking a phrase and running directly into traffic with it.

When I say my whore era, I do not mean chaos. I do not mean self destruction. I do not mean saying yes when I want to say no, chasing validation, ignoring my gut, or treating people like disposable side quests.

I mean choice.

I mean curiosity.

I mean letting myself want things without immediately putting myself on trial.

I mean being able to flirt without wondering whether it makes me a bad person. I mean dating men without acting like I need to become fluent in queer confidence overnight. I mean pleasure, safety, kindness, honesty, and a little bit of lip balm before leaving the house.

I mean agency.

For a long time, I thought I had to understand everything before I was allowed to try anything. Labels, desire, dating, sex, what I wanted, what it meant. I treated identity like an exam I had somehow missed the revision session for.

I wrote more about that in Am I Bi Or Gay? Stop Overthinking Labels, because honestly, the label spiral deserves its own little padded room.

What helped most was realising I did not need to solve my entire identity before letting myself have a life.

I could move slowly.

I could change my mind.

I could enjoy myself and still be thoughtful.

Revolutionary. Annoyingly simple.

The Part I Did Not Want To Admit

I did not want to admit that some of my early confidence was actually nerves in a leather jacket.

I had come out later than some people. I had ended a long relationship that mattered. I had spent years being honest in some ways and very much not honest in others. When I finally started dating men, there was a part of me that felt like I needed to catch up.

As if queer life was a train I had missed.

As if everyone else had been handed a manual at twenty one and I was arriving breathless with a cracked phone screen and no idea what the etiquette was.

That is a dangerous feeling, because it can make you confuse speed with freedom.

It can make you say yes because you are scared of seeming inexperienced.

It can make you ignore discomfort because you think discomfort is just part of learning.

It can make you perform chill when what you actually need is clarity.

I learned this the hard way, obviously.

My notes app has seen things.

Rule One: I Do Not Audition For Desire

This one took me a while.

When you come out later, especially after being in a long relationship, it is very easy to feel like you need to prove you belong. Prove you are queer enough. Prove you are confident enough. Prove you are not too new, too awkward, too cautious, too much.

Absolutely not.

I am not auditioning.

I am not turning dates into exams. I am not pretending to be more experienced than I am. I am not laughing off something that makes me uncomfortable because I want to seem easygoing.

There is a difference between being open and being available for anything.

My current line, which I offer to you like a slightly battered but useful umbrella, is:

“I am into keeping things fun, but I do not rush stuff.”

Simple. Calm. No essay. No apology.

The right person does not need you to abandon yourself to keep the mood alive.

The mood can cope with a boundary.

Rule Two: Consent Has To Feel Normal

I know “consent is sexy” can sound like something printed on a tote bag at a student fair, but it is true.

Consent is not a mood killer. Awkwardness is survivable. Guesswork is worse.

I like people who can talk like adults. Not in a formal clipboard way. Just in a normal, human way.

“Is this okay?”

“What are you into?”

“Anything that is a no for you?”

“Want to slow down?”

These are not scary sentences. They are green flags wearing sensible shoes.

Many first timers find that the conversation feels bigger in their head than it does out loud. I definitely did. I thought talking about boundaries would make me seem nervous. Then I realised that pretending not to have boundaries made me feel worse.

Consent is not a one time box ticked at the start. It is the ongoing vibe. It is paying attention. It is leaving room for someone to change their mind without making it weird.

That includes me.

Especially me.

Rule Three: Casual Still Means Kind

This is one I will defend with my full chest and possibly a coffee.

Casual does not mean careless.

You can have something light and still be respectful. You can flirt, date, hook up, explore, or keep things undefined without becoming emotionally feral.

The bar is in hell, but I am still raising it.

For me, kindness looks like being clear about what I want. It looks like not promising more than I can offer. It looks like replying like a person, not a haunted algorithm. It looks like accepting a no without sulking. It looks like remembering that the person on the other side of the app is not there to validate my identity crisis.

My friend Priya once looked at me across the kitchen while I was overthinking a message and said, “Are you trying to be honest, or are you trying to be liked?”

Rude.

Useful.

I changed the message.

Rule Four: Safety Is Self Respect, Not Anxiety

I used to think being safety conscious would make me seem uncool.

Now I think uncool is ignoring your own comfort because you are trying to impress someone whose bathroom does not have a hand towel.

Safety does not have to be dramatic. It can be practical. It can be quiet. It can be part of the routine.

For me, that means telling a friend where I am going when I am meeting someone new. It means not feeling rude for leaving when I want to. It means having conversations about sexual health without acting like I have asked someone to explain their tax code.

It also means using products that support comfort rather than pretending my body should just magically know what to do.

Lube is not embarrassing. It is helpful. Water based lube is often a good place to start because it works with many toys and condoms. For anal toys, a flared base matters. That is not a quirky preference. That is basic safety. Stop if there is pain. Slow down if something feels off. If discomfort persists, speak to a clinician.

Look at me. Being sensible and hot.

Duality.

Rule Five: I Check In With Myself After

This was the rule that changed the most for me.

At first, I thought confidence was about saying yes. Then I realised confidence is also about how I feel afterwards.

Do I feel calm?

Do I feel respected?

Did I actually enjoy that, or did I enjoy being wanted?

Did I say what I meant?

Did I ignore anything?

Did I leave with my self esteem still in the room?

I do a little post date audit. Not a spreadsheet, because I do still want joy in my life. Just a quiet check in on the way home, usually while walking too fast because I have once again underestimated the temperature.

Sometimes the answer is, “That was fun.”

Sometimes it is, “Nice enough, but not for me.”

Sometimes it is, “Oliver, angel, you were people pleasing in a fitted jacket.”

We learn.

Rule Six: I Let The Era Change Shape

The point of this chapter is not to become a new fixed version of myself.

It is to stop abandoning myself in the name of being acceptable.

Some weeks I feel bold. Some weeks I want a quiet Sunday reset, laundry done, coffee in hand, phone on silent, absolutely no one perceived me sexually for forty eight hours.

Both count.

Exploration does not have to be constant to be real. You are allowed to pause. You are allowed to be excited and nervous. You are allowed to want connection one month and space the next. You are allowed to change your mind without turning it into evidence that you are fake.

Coming out later taught me that honesty can arrive quietly. I wrote about that in I Came Out Later In Life. It Wasn’t Dramatic, It Was Just Honest, because for me, the biggest shift was not a grand announcement. It was finally breathing properly.

This chapter feels similar.

Less performance.

More truth.

The Rules I Actually Use

Here is the list I keep coming back to. Not because I always get it perfect, but because it helps.

1. I do not say yes just to seem confident.
2. I do not confuse being wanted with being valued.
3. I talk about boundaries before resentment gets a chance to build furniture.
4. I treat sexual health conversations as normal, because they are.
5. I choose comfort first, especially with toys, lube, and anything new.
6. I leave when my body says, “We are done here, babe.”
7. I do not make my identity dependent on someone else finding me desirable.
8. I can be playful and still be careful.
9. I can be casual and still be kind.
10. I am allowed to take my time.

The Reframe That Helped Me Most

My whore era is not about becoming fearless.

It is about becoming honest.

I still get nervous. I still rewrite messages. I still occasionally stare at a dating app profile like it is a legal document. I still ask Milo questions that make him blink slowly and say, “Ollie, you are allowed to just ask him.”

But I am not trying to be a perfect queer adult anymore.

I am trying to be present.

I am trying to choose things because I want them, not because I am scared of missing out.

I am trying to let pleasure be part of self knowledge, not something I have to earn by being perfectly confident first.

That is the rule under all the other rules.

I do not lose myself to prove I am free.

Soft Landing

There is nothing wrong with wanting fun. There is nothing wrong with wanting attention, touch, flirting, novelty, softness, heat, laughter, or a story for the group chat that requires three voice notes and a walk around the block.

Wanting is not the problem.

The question is whether you are still listening to yourself while you want.

That is what I am learning. Slowly. Imperfectly. Usually with a coffee, a notes app list, and one mate replying, “Proud of you, but please eat something.”

My whore era has rules because I deserve fun that does not cost me my peace.

So do you.

You are allowed to explore.

You are allowed to be careful.

You are allowed to be a little messy and still deeply worthy of respect.

And you are absolutely allowed to take your time.