Sexual Health Without the Awkwardness: The Chat That’s Actually Attractive

I recently spent about twelve minutes rewriting one completely normal question.

“When were you last tested?”

Delete.

“Random question, and absolutely no pressure…”

Delete. Too HR department.

“Just wondering when you last had an STI test?”

Better. Still somehow sounded like I was about to request supporting documentation and two references.

Eventually, I sent something normal. He replied normally. The earth remained on its axis.

My notes app has seen things, but even it seemed embarrassed for me.

The funny thing is, I’ve spent months getting better at dating men. Better at saying what I wanted. Better at admitting when I was nervous. Better at understanding that being newly out didn’t mean I had to pretend I’d been issued some secret gay instruction manual at Pride.

I’d already written about dating men for the first time and the very humbling discovery that communication generally makes things less awkward, not more.

Apparently, sexual health was the next module.

Which brings me back to the question I was apparently treating like a diplomatic incident.

I Thought Asking Would Make Me Look Inexperienced:

This was the bit I didn’t want to admit.

I wasn’t really scared of talking about STI testing.

I was scared of exposing the fact that I didn’t quite know how people talked about STI testing.

There’s a difference.

When you start dating men later than you expected to, it’s very easy to imagine everyone else has been doing this flawlessly for years.

They know when to bring things up.

They know what questions to ask.

They presumably have a beautifully organised calendar of appointments and confidently say things like “sexual-health screening” without immediately wanting to crawl underneath a table.

Meanwhile, I was still occasionally approaching dating apps like I was updating LinkedIn.

Tragic.

A lot of this is the same pressure I put on myself when I was trying to work out whether I was bi, gay, queer or simply overthinking the entire thing.

I thought everyone else knew something I didn’t.

Then I slowly realised most people are just people.

Some are confident. Some aren’t. Some have brilliant communication skills. Some can send a six-minute voice note about their fantasy football team but become mysteriously unable to form a sentence when the conversation involves condoms.

Trying to Be “Chill” Was Actually Making Me More Anxious:

For a while, I wanted desperately to be chill.

Newly out Ollie was very committed to seeming unbothered.

“What are you comfortable with?”

“Oh, whatever.”

“What do you want?”

“I’m easy.”

I was not easy.

I had preferences. Questions. Boundaries. Things I wasn’t sure about yet.

I just thought admitting any of that would make me difficult.

I learned this the hard way, obviously.

Because what happened when I didn’t ask questions wasn’t that I became wonderfully spontaneous and carefree.

I just worried afterwards.

Had we actually talked about what we were comfortable with?

Had I agreed because I wanted something, or because I didn’t want to create an awkward moment?

Was I making sensible decisions or auditioning for the role of Most Relaxed Queer Man in Manchester?

Turns out “chill” is not a sexual-health strategy.

Devastating news for my twenties.

The shift for me was realising that safety isn’t about assuming something bad is going to happen.

It’s about respecting myself enough to make decisions with the information I actually need.

The Chat Got Easier When I Stopped Treating It Like an Interrogation:

I think part of the awkwardness comes from how we imagine these conversations.

“When were you last tested?” can sound, inside your head, suspiciously close to ‘Please provide evidence that you are an acceptable human being.’

That isn’t what I’m asking.

I’m not asking somebody to prove they’re “clean”, because having an STI doesn’t make somebody dirty.

I’m not asking for their complete sexual history.

I’m definitely not getting a desk lamp and demanding names.

I’m asking because we’re both allowed to make informed choices about our bodies.

That’s it.

What I Actually Say Now:

I am not suggesting you memorise a script and deliver it while maintaining intense eye contact.

Please don’t blame me for whatever atmosphere that creates.

But having a few normal sentences ready genuinely helped me because it stopped every conversation feeling like I needed to invent the perfect wording on the spot. Keep it simple:

“Just checking — when did you last get tested?”

Or I’ll lead with myself:

“I got tested recently. When did you last do yours?”

Sometimes:

“Before we go any further, can we do the boring responsible bit for thirty seconds?”

That one feels particularly me.

The important bit isn’t finding a magical sentence.

It’s asking the question clearly enough that both of you know what you’re talking about.

I used to think I needed to make every preference sound negotiable.

I don’t anymore.

Knowing My Own Sexual Health Made the Conversation Easier Too:

There is a point where my lived experience stops and actual medical advice needs to begin.

My notes app does many jobs. Being a qualified sexual-health professional isn’t one of them.

What I have learned is that I feel much calmer discussing testing when I’m also taking responsibility for my own.

The NHS notes that many STIs don’t cause symptoms, which means you can have one without knowing. Testing is therefore the way to know your status rather than relying on whether somebody looks or feels completely well.

That’s been an important mindset shift for me.

Testing isn’t something you only do because you think you’ve been reckless.

It can simply be part of looking after yourself when you’re sexually active and meeting new partners.

Their Reaction Is Information Too:

Something else I’ve learned: you can tell quite a lot from how somebody reacts when you bring this stuff up.

Not whether they’re perfectly smooth.

Smooth isn’t the goal.

Somebody might stumble over the conversation. They might be embarrassed. They might need a second.

Fair enough.

I have personally turned one question about STI testing into a twelve-minute notes-app event. I’m not judging anybody for mild awkwardness.

What matters to me is whether they’re willing to talk.

There’s a big difference between:

“God, I never know how to have this conversation either, but yeah…”

and somebody dismissing your question, making fun of you or pressuring you to drop a boundary.

I don’t need perfection.

I do need respect.

And I’m becoming much less interested in convincing somebody that my comfort matters.

Someone being momentarily awkward doesn’t bother me.

Someone making me feel ridiculous for asking does.

That’s not drama.

That’s information.

My Very Unsexy Sexual-Health Checklist:

Things I’m learning (don’t be cringe):

• Ask before you’re completely caught up in the moment. I find conversations easier when nobody feels rushed.
• Lead with yourself if that feels easier. “I got tested recently…” often feels more natural than firing questions at somebody.
• Say what you’re comfortable with clearly. Especially around condoms, barriers and other boundaries. “I’d rather…” is enough.
• Don’t rely on symptoms. Many STIs can have no symptoms, so testing matters.
• Remember that consent can change. Agreeing to one thing isn’t automatically agreeing to everything else, and anyone can change their mind.

Protection and Pleasure Aren’t Opposites:

I used to have this weird idea that preparing for things would make them feel less spontaneous.

I’ve changed my mind.

Having condoms around doesn’t mean I’m assuming anything will happen.

Knowing what makes me comfortable doesn’t make me boring.

Keeping a decent lubricant nearby isn’t exactly an admission that I’ve become someone’s dad.

It just means I’d rather make comfort easy than discover at an inconvenient moment that optimism isn’t actually a substitute for lube.

If you’re building your own version of the sensible drawer, you can browse condoms or explore water-based lubricants without turning it into a major life event.

For anything involving anal play, comfort matters particularly. Use plenty of suitable lube, go slowly, and stop if there’s pain. If you’re using anal toys, choose something designed for anal use with a flared base so it can’t travel fully inside the body.

Nobody gets a prize for rushing.

I checked.