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Thoughts from the Hobbit House | I Made Every Gay Dating Mistake So You Don’t Have To

Robert and Ryan

A public service announcement & gay dating guide no one asked for, but many desperately need.


Let’s start with a disclaimer.

This is not a guide to straight dating. I am wildly unqualified for that. If you need help navigating heterosexual courtship, I suggest literally anyone else.

This is a guide to gay dating.

If you are a gay man—or have ever considered dating one—congratulations. You are the target audience for this deeply questionable expertise.

Why should you listen to me?

Because I have, with remarkable consistency and commitment, made nearly every mistake in the gay dating handbook. Not just once. Repeatedly. With confidence.

And yet—against all odds—I somehow ended up married to an incredible man who is also my husband (yes, both things can be true) and who has tolerated me for the past ten years. Scientists are still studying how.

Also, an ex-boyfriend once told me,
“I’m glad I dated you because I learned all the things I don’t want in a relationship. I was then prepared to meet my husband.”

So, to summarize: dating me prepared him to find the love of his life…who was not me.

Which, if you think about it, makes me less of a romantic partner and more of an emotional internship. An internship that led him to getting the job- err husband he always wanted.

So yes, I think we can all agree, I am extremely qualified to author this piece.

My first piece of advice when it comes to gay dating:

Don’t.

For the love of Pete and all that is good and emotionally stable—don’t do it.

However, if you insist (and you will), here’s what to do—and more importantly, what absolutely not to do.

Note: All of the following events occurred before I married my dear husband, who I would like to remind you is still here voluntarily.


Don’t Leave Love to Chance

In my twenties, I once locked eyes with a fellow who was witty, charming, and unfairly attractive while he waited on our table.

At the end of the meal—fueled by courage and carbohydrates—I wrote a note on a napkin:

“I love your smile, and I’d like to see it again. –Ryan”
(plus my phone number, because I am nothing if not thorough)

I folded it into a delicate paper flower and left it on the table like a rom-com protagonist who absolutely wasn’t about to ruin his own life.

The next day, I received a text:

“I liked your napkin note flower. I’d like to see your smile too.”

Reader, I levitated.

We arranged to meet for coffee. I arrived early, emotionally prepared, radiating what I can only describe as “medium confidence.”

And there she was.

A lovely, enthusiastic woman in her 50s.

The hostess.

As it turns out, she had cleared the table, found the napkin, and—bless her optimistic heart—assumed it was for her.

And honestly? Respect.

Now, you might be wondering how long it took me to clarify the situation?

Over an hour. We’d made it through two coffees and an appetizer.

Because once you’ve accidentally asked someone out via rogue napkin, there is no graceful exit. There is only commitment. There is only suffering.

Eventually, I gently explained.

I still think about her sometimes. I hope she found someone who writes her intentional napkin notes.

And I hope you learned something important here:

Always. Write. The. Name.

Or better yet—don’t flirt using table linens like you’re in a low-budget Nicholas Sparks adaptation.


Don’t Rely Solely on the Internet

I once met a guy online who lived over ten hours away in Utah.

Ten. Hours.

Which, in gay dating terms, is either a red flag or the beginning of a deeply unnecessary emotional saga.

(Spoiler: it was both.)

We talked for six months.

Six.

Months.

No meeting. Just escalating emotional intimacy and increasingly unhinged future planning:

  • “What will our retirement look like?”
  • “Where should we live?”
  • “What should we name our first dog?”

(We had not yet confirmed if we could tolerate each other chewing.)

Eventually, he drove ten hours all the way to Spokane so we could finally meet and spend a week together.

He arrived with flowers. A handwritten love letter and poem.

He read the letter.

He read the poem.

Then he looked at me and declared:

“I am in love with you. You are the love of my life.”

And that…that was the exact moment I knew.

This was not going to work.

Six months of talking.
Ten minutes of reality.

It took me twenty more minutes to say,
“I don’t think we’re compatible…”

He cried. He left. He drove ten hours back.

To this day, I feel awful.

But then—plot twist—he wrote a fantastic article for a national publication about the asshole in Spokane who broke his heart.

The asshole was me.

And honestly?

He wasn’t wrong.

So here’s the lesson:

Don’t rely solely on the internet to connect with someone. For both your sakes.

And also:

Don’t be an asshole.


Do: Weaponize Snacks

At this point, you may notice a pattern:

Two “Don’ts,” very little evidence that I know what does work.

That feels correct.

But I do know this:

Food works.

Apparently people need food.

When I was trying to win over the man who would become my husband, I did not rely on charm.

I relied on snacks.

For months, I left small, thoughtful food offerings on his desk.

Nothing overwhelming.

Just enough to say:
“Hello. I exist. I am kind. I have access to excellent snacks.”

It was less of a courtship and more of a breadcrumb trail.

Eventually, when he got hungry enough, he followed the snacks back to me.

And the rest is history.

So let this be your takeaway:

Flowers wilt. Texts get ignored. Personalities crumble.

But men need snacks. Even gay men need snacks.

Use delicious foods to land a delicious fellow.

My delicious fellow was partial to Cool Ranch Doritos.


Don’t Rely on Temporary Tattoos…or Whatever This Was

If you are my parents—or any extended family member who somehow got their hands on this—or my colleague or my colleague’s colleague— for the love of Pete (still no idea who Pete is), please stop reading immediately.

Seriously.

This is your exit.

Alright. If you’re still here, that’s on you.

Now, at one point in my life, I told myself I was going to “save myself for marriage.”

That might be a lie.

A bold, unnecessary lie.

What I did tell myself was that I would at least wait until the fourth date. Maybe the third. Ok, at least the second. Long enough to establish that we could, at minimum, tolerate each other in daylight.

The problem?

I am a man… I am a very GAY man.

A very human, very flawed, occasionally and often overly enthusiastic man.

And this turned out to be…challenging.

So, like any rational adult, I developed a system.

Before a date, I would take a permanent marker and write across my abdomen:

“I have an STD!”

(Yes, with an exclamation mark. Why? Science does not know. My therapist has theories.)

This, I reasoned, would ensure that no impulsive decisions were made. A built-in accountability measure. A moral safeguard. A deeply unhinged but effective strategy.

And you know what?

It worked.

Right up until it absolutely did not.

One evening, I went on a date with a man who was charming, attractive, and—dangerously—very good company with abs to match. The kind of date where you start making highly questionable decisions.

At some point, I suggested we go late-night skinny dipping.

Because clearly, nothing says “good decision-making” like removing both clothing and safeguards near a body of water.

But I had a plan.

It was dark.

Surely he wouldn’t see the writing.

And if he did? The water would wash it off.

Reader, the water did not wash it off.

What it did do was smear the ink into something far more confusing.

At one point, he grabbed my arm, squinted at my torso, and tried to decipher the now-blurred message.

After a long pause, he looked at me—deeply concerned—and asked:

“…Are you in the Spokane Police Department?”

Because, apparently, what he read was:

“I’m the SPD!”

And just like that, the evening took a sharp and irreversible turn.

Nothing kills the mood quite like accidental law enforcement impersonation.

Especially enthusiastic law enforcement impersonation.

The date went downhill from there.

So let this be your takeaway:

If you feel the need to write warnings on your own body as a dating strategy…

DON’T. You may need a different strategy.


Don’t Do Something For Them They Explicitly Told You Not To

This one feels obvious.

Painfully obvious.

So obvious, in fact, that you might be thinking, “Surely no one needs to be told this.”

And yet…here we are.

According to my now-husband, this particular moment in our early dating life came alarmingly close to ending things.

Which, in hindsight, feels fair.

At one point, I went through a phase where I believed—deeply, passionately—that every window in a home should have a window seat.

Not just some windows.

All windows.

Was this based on architectural training? No.
Was it based on logic? Also no.
And yet I proceeded with building window seats for every window anyway.  

Around this same time, I decided my then-boyfriend’s office could use “a little organization.”

So, being a reasonable person, I offered:

“Would you like me to build you some shelves and a window seat?”

He politely declined. Several times. Because I’m annoyingly persistent.

A normal person would hear this and think, “Great, boundary respected.”

I heard this and thought:

“He doesn’t yet understand how much he needs this and how much he would enjoy a window seat on which to sit upon and gaze out the window.”

So I did what any deeply misguided but enthusiastic partner would do.

I waited until he left.

And then I built it anyway.

Not just a shelf.

Not just a tasteful addition.

A full-scale construction project.

Shelves.

A window seat.

An entire wall transformation.

Then, because I am nothing if not thorough, I went through all of his belongings and organized them onto the shelves.

Because I told myself I was helping.

When I finished, I closed the door, tied a metaphorical bow on the situation, and waited.

He came home.

I led him upstairs.

He opened the door.

And I, filled with pride and absolutely no self-awareness, yelled:

“Surprise!”

Which, loosely translated, meant:

“Here is the thing you explicitly said you did not want, but I decided you needed anyway.”

Reader…he did not love it.

In fact, I believe the phrase “What did you do?” was involved.

And possibly several others that are not suitable for print.

The relationship did survive.

Barely.

But let this be your takeaway:

It is not romantic to ignore someone’s clearly stated wishes.

It is not thoughtful to override boundaries with enthusiasm.

Not every window needs a window seat.

And it is definitely not a good idea to reorganize someone’s entire life when they told you not to.

Do not make decisions for them. Make decisions WITH them.  

 

Do: Loudly Announce You’re Done Dating Forever

At this point, I feel a moral obligation to provide another “Do,” since I’ve already issued several “Don’ts” and at least one public apology.

So here it is:

Do loudly proclaim—to anyone who will listen, and especially to the universe—that you are done with dating and fully committed to being single forever.

I’m serious.

After a truly impressive streak of poor decisions, I reached a point where I thought, “You know what would be good for everyone involved? If I stopped.”

For my well-being.

For the well-being of other gay men in the greater Spokane and Washington (and even one in Tennessee) area.

For public safety.

So I did the work.

I looked myself in the mirror. I reflected. I grew. I deleted the apps. I retired the “three buttons mysteriously undone on my shirt” look (universally understood in gay culture as “available and making questionable choices”).

I stopped bleaching my hair and wearing puka shells (also universally understood in gay culture as “available”).

I committed.

Fully.

To being single.

And then—because subtlety has never been my strength—I essentially announced to the universe:

“I AM DONE. I CHOOSE SOLITUDE. I WILL BE ALONE AND THRIVE.”

The gay dating gods heard this.

Paused.

Exchanged knowing glances.

And, with a dramatic flick of the wrist, said:

“Oh…that’s what YOU think.”

Because quicky thereafter they dropped an intelligent, handsome, charming man directly into my workplace.

My workplace.

My carefully constructed, drama-free, personal-growth zone.

I tried to resist. I really did.

But then he smiled.

And three of his buttons were undone and his hair was bleached.

And just like that, all my hard-won commitment to singleness melted faster than ice cream in July.

Reader, I was done for.

Completely smitten.

I started depositing Cool Rach Doritos on his desk.

So here’s the lesson:

Absolutely work on yourself.
Absolutely commit to being single.
Absolutely announce it with confidence.

Because that is the exact moment the gay dating gods will notice you, laugh, and send your future husband directly into your line of sight.

You’re welcome.


Final Thoughts

Gay dating is chaotic, illogical, and occasionally traumatic.

But it’s also hilarious, human, and—somehow—worth it.

Even if, along the way, you accidentally ask out the wrong person, break someone’s heart, impersonate law enforcement, gift something they didn’t want, and lure your future spouse with Cool Ranch Doritos.

So go forth.

Make mistakes.

Learn something.

Bring snacks.

And for the love of Pete—

write their name on the napkin.

Ryan Oelrich is a highly regarded mental health trainer and facilitator, having trained thousands of professionals since 2008. He’s developed mental health curriculum used by Washington State. He is a Robert Wood Johnson Foundation Culture of Health Fellow and has an MBA and an MA in Leadership. Oelrich was awarded the Peirone Prize for service in 2016 and has received congressional recognition for his work on poverty and homelessness issues. Oelrich has founded 3 nonprofits focused on youth issues, and he’s an advocate for increased collaboration and coordination.

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