Dating Into Oblivion, ep1

Well, this little endeavor is off to a great start.  I hope you all enjoy this as much as I am so far.

To recap: my goal is to throw $20 at a date once a month and see what happens.

What could possibly go wrong?

It’s like I threw a party and no one came.

Don’t read too much into that last word.

And here’s the deal, I could see throwing a party and maybe no one shows up.


But today was the 4th time it’s happened.  Technically, the 3rd and 4th time.  That’s how quickly my faith collapsed inward, I scheduled two dates in one afternoon.

But it wasn’t always so grim.

It started off much worse.

My first attempt crept on me.  I went into a bar after seeing a movie one afternoon early this month.  

The bartender hit on me.

Flattering.  It wasn’t the first time, either, and it was appreciated.  But I didn’t dwell on the prior instance and just enjoyed the moment.  He went to the bother of finding me on the Facebook Messenger later that night…we aren’t friends on the Facebook, so I decided to be impressed by the minimal effort that required.

I really do have the bar set low.  Like, ground level.  It’s left me quite dumbstruck how hard guys make clearing a low bar look.

So, me and the bartender are talking about meeting up and I mention how interested I’d been in dating him since the first time I met him.

He goes silent-er.  Instead of multiple daily messages, it’s a response every other day and he’s steered clear of actually committing to a date/time.  Reading between the lines, I dial it back and say that if he’s looking for casual, it’s not really my thing but I’d give it a second thought with him.

Then it hits me.

“Oh my GOD.  You’re still MARRIED, aren’t you?!?”

The first time I met him, I’d been sitting at the bar at Hobo’s talking to Everybody’s Uncle Dave.  His group walks in and he tracks me as he walks by and bee lines it for the bathroom.  As is my usual lot in life, his friends pick the barstools immediately next to mine on this 40 foot long bar.

When he comes out of the can, instead of sitting on the other side of his friends, he hops into my lap.

He’s significantly attractive, so I cannot care.  He gives me his number quick and says we should get together.  

As I’m listening, it becomes obvious that this is his Stag Party and he’s getting friggin’ married.

Picture me standing up, him sliding onto his adorable butt on the ground and me leaving, because I think that’s what actually happened.

So, the second time around was about as elegant…he never replied.

Shake it off, Galby.

The second attempt moved from real life to something less analog, but still kinda quaint in the age of apps.  I’ve kept one asocial media website profile active for the last forever.

I was on said site and sent off a few smiles.  I keep it light, usually.  Im an older guy hitting on younger guys, if they don’t want to engage, I take the hint.

A nice looking guy bothered to strike up a conversation.  His profile had several private pics, which he kept locked.  I appreciated this, since if it’s meant to be something I see, it’ll be in person.  So many of these gay-tards (Chrisism) think they have no value past their sexual use that I usually know what someone’s junk looks like before I know their name…if I ever even get to know their name.

We talked for about ten days, discussing getting together and setting a date to meet.

This being my life, he cancelled because he got a job interview.  Priorities.  I get it.

Suddenly, his pics are unlocked.

I explain that I don’t want nor do I expect to see them and why.  Then he says he feels bad…but doesn’t lock them.

Several days go by.

I don’t visit the site often, but get an email every day that I have mail waiting.

Finally, I log in to make sure I didn’t miss something.

No mail.

And his pics are still open.  Since it looks like he’s never going to talk to me again – so dramatic – I take a look to see if his 28 year old physique matches his cute mug.


It’s like the very reason I don’t have boudoir pics.  On a guy that has about 40% less reason to excuse said reason.

Why?!?  No, not “why?”  I think I’m actually jealous that this guy is so comfortable in his skin to have these pics.

My mind is fairly boggled.

But, I do never hear from him again.

Attempts three and four happened concurrently.  It wasn’t anything impressive or typically Portland, like a couple trying to date me.  These two opportunities simply presented about the same time.

Me, being old and prone to confusion, asked them both out on the same day, today…which happens to be my Saturday.

Attempt three is someone who responded to a personal ad I placed.  Talk about old school.  He replied, included a face pic and a couple unsolicited and unexpected but not unwelcome – see above – body pics.  It’s ok, technically, since his name was in his email address.

He seemed nice and charming and genuine.  We set up a date to meet – today – which happens to be both our day off.  His only day off since he works full time and is a student.

Shut up, he’s 38.

My red flags are two:

He works nights, I work days.  We might only have one day per week to get to know each other.  

My second hesitation was that he’s from Mexico.

Hey, it can be a turn on and red flag at the same time!

My concern is that with English being his second language and so much of my persona being…snarkiness, a lot can get lost in translation,

I was impressed that he followed up to confirm this morning at 8:30.  I had an acupuncture appointment at 8:15, but replied at 9:30 when I got out.  

“Just give me a when and a where and I’m there”, I say.

At one o’clock, I’m still waiting.

I go scrolling through the Craigslist, killing time.  Also, maybe I need to be looking for February’s no-show.

I mean, date.

I click on an af that sounds up my alley.

There’s a few pics I recognize.

“Looking for today”…posted seven hours ago.

I’m having trouble getting my mind around someone who places this ad, emails me to confirm our date an hour later and then goes silent on me.

Obviously, he’s getting laid.

Only possible conclusion, right?  Setting aside my conviction that if he’s got…well, nevermind.  The point is, I call him on it.

He responds within minutes.

Full stop.  I’ve waited about four hours for you to give me a when and a where and when I tell you, “I get it, it’s your only day off for the week.  Take care of business” you suddenly have all the time in the world to respond?

Unfortunately, he chose to respond with, “You know how flakey gay guys are.  But I really want to see you!”

Yes, I do know how flakey gay guys are.  And I am not able to reconcile how four hours goes by without you picking a fucking time and coffee house while seven minutes elapsed between my j’accuse moment to his sudden reply.

Which brings us to my 4th attempt. 

This is a cute kid that I didn’t meet a couple of years ago when I moved back to town. 

I don’t drive + he lives in Vantucky = we never met.

But, we were already connected on the Facebook and when I joined the instagram last year, he was a suggested follow.  So, now there’s that.

Which is where I got into trouble.

But before that, last year, he got into a wreck that left him laid up for quite a while.  Long enough that he lost his entry level job at a quick serve restaurant and I’d been following his job search via status updates for a while.

I’m always – literally, if you know someone looking in Portland, OR let me know – hiring, so since we didn’t date I felt absolutely no awkwardness about extending an opportunity his way.





Oh, well.

I thought about following up, but do I really want an employee I had to chase down to apply working for me?


No, I don’t.

Some of the ones that voluntarily applied are enough of a probl…challenge.

So, I let it lie.

Then last week, we got into a DM on the Instagram that ended in him giving me his number.

We move to text and go at it like teenagers for a few days.  I can tell he’s no conversationalist, but get the vibe that he wants me to ask him out.

I do.

Thursday evening, about 6 or 7?


I check in last night with a text, a 24 hour confirmation and hear nothing.

That was 22 hours ago and I don’t know if my thoughts are along the “Fucking millennials” or “Fucking fags” line.

Still…fucking something.

I do know that after a couple of years of not knowing him in real life, I feel as if I know what he wants or needs better than hizownself does.

He’s a Lost Boy.  That doesn’t make him a bad person, just lost.  Nothing more, nothing less.  But with potential in both directions, depending on whether he pulls his head out of his ass sooner, later or never.

I can say that my prior inclination to “raise” – for lack of a better word – a younger gay into a man is…not gone, but certainly sublimated.  I think it’s the job of a partner to help their SO become a better and better version of themselves.  I’m just aware that not every cute guy I come across with his act lying in shambles around his ankles isn’t automatically a perfect fit for me.

That’s a good realization.

There you have it. Episode 1 of Dating Into Oblivion.  Meanwhile, I’ve saved $80.  I’ve also enjoyed two and a half beers at Big Legrowlski while tapping this out.

And flirted with a probably straight guy over sci-if books.  So there’s that.

In theory, I’m quite an attractive option.

In reality…50 (minus 80-ish hours) and single, people.

Dating Into Oblivion, ep1

6 thoughts on “Dating Into Oblivion, ep1

  1. Masculine Perspectives says:

    Wow. The games some guys play. I’m a divorced (it’s been ten years officially but at least 12 twelve since my marriage really broke up) bisexual; one who’s been trying to understand this whole “find and [try to] date a dude” (or at least fuck a dude) game for years. While I’ve been fortunate to have had several “one-night sands” (Do they still call them that or am I showing my age) in recent years, – with a couple of regular fuck buddies over the years (since I decided to leave women alone and pursue my stronger passion for men), I’ve yet to find any guy (and apparently, he hasn’t found me) to date. In short, g, I’ve never dated a guy. Ever.
    Reading your escapades (for lack of a better word) kinda encourages me into realizing that for older, serious, “got-their-head-together” type guys…that is, men like us who already know what they/we want, it seems (and I’m judging only from my limited post [hetero]-marriage experience) that guys like us are in the minority (depending on location, I suppose) among a bunch of younger and/or probably same-aged guys who don’t know what they want, and/or who aren’t willing or can’t be serious, and for whom sex is everything. The “establishing and nurturing a friendship” factor is not part of the game. That alone is fuckstrating to me.
    Well, at least I enjoy reading how you’re still willing to put yourself out there. You must be younger than me and have a lot more practice and patience. I’m short on practice and am patient (often without choice) but my patience has its limits. Still, constantly do I tell myself that I need to put myself out there more often; if for no other reason than the possibility that the kind of guy I’m looking for just might find ME. I also need to not let my age (57 though I’m told I look ten years younger – if that matters) be a hindrance. I’m not a bad looking person by any measure. I just do not know what supposedly serious, mature, same-gender loving guys want – assuming of course, there live in my area.
    ANYWAY, sorry for the long comment, Galby. Thanks for sharing a good story. Be well, g. ☺️

    Liked by 1 person

    1. Ok, first…fuckstrating is a great word. Love it! But I can’t believe you trot that out and leave sexcapades in the stable in place of escapades. 😂
      Second, thank you for reading and taking the time to comment. It means a lot to me.
      And, third, here’s some maybe good news. My best friend – The Silver Fox is his blog name – has a similar life arc as yours. Was that bad English? I think it was. Anyhoo, I think he made his life change around 50 and has managed three long term situations in the decade and a half since. So there’s that. And, if my dating success continues, I have him and he has me. We call each other NSLPs, which stands for non-sexual life partners, and we are neighbors separated by a park. If that’s my longest term relationship, I can highly recommend it! 😊

      Liked by 1 person

      1. Masculine Perspectives says:

        Hmmm… it sounds like your NSLP friend, Silver Fox may have a blog that interests me. I’ll look his name/blog up and check it out. Thank you!
        And the word “sexcapades”; of course, g! That indeed is a more fitting word to use than “escapades”. LOL! Thanks for the reminder, Galby! I suppose it did not occur to me simply because it’s not a word I use regularly, while “fuckstrations” on the other hand is one I’ve been using (in both verbal and written form) in lieu of “frustrations” for about thirty years or so. ☺️ Have a great day and an awesome weekend!

        Liked by 1 person

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