Page 2 of Pink Cheeks (DKAG Summer Shorts #2)

DOUG

Take this job and you can work from anywhere…

That was the promise when the offer letter still felt like a lottery ticket and not a veiled threat.

They gave me a hell of a package with generous options, a huge bonus plan, and the kind of health insurance that actually insured you.

But the real golden goose, or so they said, was unlimited time off and remote freedom.

What was it that they said about things being too good to be true?

In reality, the only place I could work from was my condo in the city, because if I was logged in from anywhere else, the security team sent me a polite but menacing email about geofencing, VPN compliance, or the risks of working from Starbucks.

Half the time, I couldn’t even use my phone hotspot without the MFA timer running out and locking me out for the afternoon.

If I had a dollar for every time someone in leadership chirped about work-life balance, I could buy my own airline and not have to worry about firewalls or deadlines for the rest of my life.

I had exactly one point of contact in HR and he was an idiot.

A gen-Z’er with a condescending smile and a stickered MacBook who once scheduled a “mandatory self-care training” at 5:00 a.m. Pacific to be inclusive of our global colleagues.

This kid liked to tell me to just close the laptop and be mindful of the present.

That was great, but then when he gave me the stink when I mentioned taking some of my unlimited PTO to go to a wedding, I was tempted to put him over my knee and remind him to respect his elders.

The CEO, on the other hand, was old school.

Corbin was the main reason I took the job in the first place.

I’d known his family for years, and he was a good man.

When I ran into him in the breakroom and sighed a little too heavily at the constant dings of my phone, he helped me make the decision I’d been struggling with for weeks.

“Son, you’re putting in too many hours. You’ll burn out and end up like one of those guys who marries his toaster or some shit.

Take a trip. Hell, take two. That’s what all those PTO hours are for.

” I’d never appreciated the man more. And since it was straight from his mouth, I felt like I could actually do it.

“Work will wait. Not everything else does.”

So I did it. I transferred a nice chunk of my signing bonus to my checking account, dusted off an old Hawaiian shirt from my dad’s sixty-fifth birthday luau, and booked a ticket to Maui.

Jake seemed surprised when I told him I was gonna be at his destination wedding, and since I hadn’t seen him in person since grad school, that was fair.

But a few days in the sunshine without access to my work account would do me some good.

And if I were really lucky, maybe they’d be some cute cabana boy to help me unwind in the way I was long overdue for.

The only thing I hated more than flying was being stuck on a plane with people who loved it.

There was something particularly annoying about frequent flyers who treated boarding like a competitive sport, shoving to the front and hoarding bin space as if they were entitled to fit their entire household in those little boxes. Other passengers be damned.

I was in no hurry to fight with them and was happy to wait for the crowds to die down.

That’s how I ended up in a lounge at SFO, three hours early and methodically sipping complimentary Jack and Cokes.

It wasn’t completely relaxing but it was better than being at work.

When I finally headed to the gate, I went straight to the counter and asked if I qualified for any upgrades.

I wore my suit to pretend I looked like someone they’d want sitting in the front, but she just shook her head and turned away without comment.

As soon as I sat down in my back-of-the-plane seat, I wondered if it was too late to buy a business class seat after all.

Being wedged between a family of six and a man who looked like he’d just finished a hotdog-eating contest made me a little sick to my stomach, but I didn’t plan to stay awake for long.

Those drinks were doing their job and my eyes were shut before we even pulled onto the runway.

The flight passed in a blur, and I didn’t wake up until a flight attendant was gently nudging me to choose a sausage breakfast burrito or veggie stir fry. My mouth tasted like gym socks, so I took the burrito and a glass of orange juice just to perk myself up.

The descent into Kahului was all turbulence and low clouds until a spike of terror rang through me when the wheels didn't hit the runway exactly when I expected, but we were on the ground, and I was more than ready to start my vacation.

It was likely to be the last one I took for a long time, so I needed to make the most of it.

After grabbing my suitcase from baggage claim, I hopped in a taxi for the half-hour drive to the resort where the wedding was being held while scrolling through Instagram and trying to remember Jake’s fiancée’s name.

It was like Kelly…but not Kelly. Maybe Kiley. No, Kaley. Definitely Kaley.

I’d been told the Four Seasons at Wailea was “nice, but not fancy.” They lied.

It was the kind of place where the valets wore white gloves and the cocktails had more accessories than I did.

I half expected my parents to put me in an old storage room, but they had me in a suite that overlooked the pool and a horseshoe of turquoise ocean.

There were two weddings happening on the lawn that afternoon, both featuring inflatable flamingos and a small army of shirtless twinks in matching board shorts.

Maybe I needed to do a little exploring before the rehearsal dinner. No harm in seeing what amenities the resort had to offer…

The rehearsal dinner was at six.

By five, I was three drinks deeper into my vacation buzz and had yet to unpack.

I’d intended to wear something light and festive but ended up in a linen button-down and khakis.

With some time to kill, I lingered in the lobby and scanned the parade of guests who passed me by.

It was the perfect time to play a little game I liked to call “Spot the Closeted Groomsman.”

There were some strong contenders.

Jake found me before I had a chance to make it inside the restaurant.

The wedding party had just finished their actual rehearsal on the beach, and it was time to party before the big day.

He hadn’t changed much since undergrad. He had the same shit-eating grin, same broad shoulders, and the same ability to make you feel like no time at all had passed since we last hung out.

He hugged me with genuine affection and a pre-wedding buzz of his own.

“Doug! Jesus, I thought you’d show up in a tracksuit and flip-flops. You look like you own the place.”

I chuckled and patted his back. “Don’t let the linen fool you. I’m just pretending to relax. The rest is booze.”

He introduced me to the cluster of friends, cousins, and at least three ex-boyfriends I’d tried and failed to forget that were walking with him.

The bride floated in on a cloud of perfume and satin and came straight to me.

“You must be Doug. Jake is so glad you could make it.” She was beautiful in a way that made you want to protect her, but also like she might know exactly how to break your kneecaps with a stiletto. I liked her immediately.

“That’s me.” I returned her hug. “It’s wonderful to meet you. Thank you for inviting me.”

I fell into easy conversation with the group, trading stories of college debauchery and mutual acquaintances lost to suburbia or mortality. The wine flowed and dinner was served. It was so much more fun than I’d expected. For a minute, I forgot why I was ever reluctant to come.

I was loose and smiling until the subject of “plus-ones” came up and a sharp elbow found my ribs. “Dougie, you didn’t bring anyone?” Ryan, one of the groomsmen that we also went to school with, was waggling his eyebrows at me. “Don’t tell me you’re still living that bachelor life.”

“Just me, myself, and I.” I shrugged and took a drink of my scotch. “Wanted to be open to what the island has to offer.”

“Cheers to that.” He laughed and clinked my glass. When the conversation changed, he leaned closer to me. “Let me know if you want company after-hours. I’m here alone too, so…”

“Okay.” I raised an eyebrow, flattered and a little surprised by the offer. “I’ll keep that in mind.”

There was a familiar spark in his eyes. We’d hooked up once in college, but the next day, he made it very clear he was straight and it would never happen again. I didn’t think about him much after that, but maybe things had become more clear for him. “I hope you do.”

Ryan was a good-looking guy who had aged well, but he wasn’t really my type. He’d probably be fun for a night, but he wasn’t the submissive type. The one time we were together, I bottomed for him. That wasn’t how it would work if we were together again. But, I was willing to keep my options open.

You never knew what or who the night might serve up.

After dessert, the crowd thinned and the afterparty migrated to a poolside bar.

The bride and groom got cozy under the tiki torches while the rest of his buddies swapped stories and made half-assed passes at the bridesmaids.

Some finance bro circled back and challenged me to a game of pool.

It was fun and reminded me that I needed to have fun more often.

There was more to life than work, and I’d forgotten that somewhere along the way.

By midnight, the bar was nearly empty, so I made my way back to my room. The air was thick with plumeria and ocean salt, and my mind was pleasantly numb. I stared at the ceiling fan for a while, letting the room spin before I closed my eyes and drifted off to sleep.