Rolling down my window, I couldn’t resist. With a grin, I
called out, "Hey, Sailor! Need a ride?"
He laughed, jumped in, and just like that, our first date
officially began.
As we drove, he asked me to pick the restaurant. That’s when
my brain went into absolute overdrive.
I wasn’t a fancy person, and I definitely didn’t want to
spend all of his money—especially if it might put him in an awkward spot. But at the
same time, I didn’t want to default to fast food either.
And so began the great restaurant dilemma.
I overthought everything. Should I pick something
casual? Would a sit-down place be too much? How do I balance making it feel
like an actual date without making it too formal? Am I the only person who
spirals into these tiny decisions before a date? Geez.
Hours ticked by as we drove through San Diego, deep in
conversation, and yet—I still hadn’t made up my mind.
Finally, I pulled into Denny’s. Simple, easy, no pressure. A
place where the focus could stay on us, rather than the menu.
Honestly?
If a guy can’t handle a $12.48 Denny’s tab, I might need
to reconsider my options.
With dinner wrapped up and no financial crisis in sight, it was time to figure out our next move and where the night took a turn.
We headed to Wrangler’s Roost, referred to simply as "the Roost", a
country-western bar where you could always find a live band, friendly people
and a dance floor that took you outside through one door and back in through
another.
And Pat? Pat wasn’t just ordering drinks—he was
orchestrating them.
A former bartender, he leaned confidently against the
bar, rattling off drink names like a seasoned pro, instructing the bartender
step by step on how to mix each one.
"You ever made this one before?" he’d ask
with a smirk.
What started as a simple round quickly spiraled into
something resembling a bartender’s boot camp, with Pat leading the
charge. The bartender was loving every second of it—grinning as he took
on the challenge, following Pat’s instructions, and occasionally chiming in
with his own suggestions.
Then came the drink names.
At first, it was innocent enough—classic cocktails, standard
mixes.
And then? Hop, Skip, and Go Naked.
One glass, two straws.
Try keeping a straight face while staring at someone you
barely know over a drink with that name. Ha!
We both tried—tried so hard—to be normal, to sip casually,
to make it feel like just any other drink.
But the longer we held eye contact, the harder it became.
A slow smirk. A twitch at the corner of my mouth. Then his.
And that was it—we lost it, laughing into our straws,
the bartender shaking his head with amusement.
Next up? Sex on the Beach.
Cue even louder laughter, the bartender chuckling, and me wondering exactly what I had signed up for. By now we had a crowd.
But the real kicker?
"Let’s do an Orgasm!" Pat announced.
That did it. I nearly fell off my barstool.
The bartender was chuckling now, Pat was unfazed, and I was
trying very hard not to burst into full-on hysterics.
By the end of the night, we’d spent $80.00 on drinks,
though at that point, it felt less like a tab and more like a record-breaking
mixology experiment with a side of comedy.
It was the kind of night that was impossible to plan, yet
unfolded perfectly.
And, one that led to one last date before we headed out in very different directions.
Stay tuned for date number 2!
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