My Life Lately – The Florida Keys

You’d be surprised at how much persuading it took to get me out to the Florida Keys. Even with promises of a free round-trip flight, lodging in my own resort cottage, and meals served by a private chef throughout the weekend, I was determined to stay in San Francisco tied to my priorities. I just don’t have time for this kind of thing — I’m busy! It stresses me out just thinking about going on “vacation”.

But after much convincing (and after a girlfriend promised to fly down with me), I agreed. Not without airing my grievances, of course, but I agreed.

And y’know what?
… It was actually kinda’ fun.

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Here are some of my favorite pictures from the trip:


Those coconuts were monstrously large. I lifted mine like a kettel-bell while tromping through Duval Street in Key West. Pretty sure I’m super buff now.

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A peek into online dating.

“Do my shoulders look sunburnt?” I’m rubbing my arms self-consciously, sitting across the table from a first date I actually haven’t flaked on.
“No!” He says, smiling. “You look tan, actually. Great. Gorgeous. Beautiful — y’know, you’re really pretty.”
“Okay-okay! Stop, stop,” I say, laughing and glancing around our table, embarrassed.

We’re at Elephant Sushi, and this is our first time meeting face to face. He’s handsome. Tall. Tan. And he carries himself well.

So far, so good.

“Why are you on Hinge?” He’s smiling at me, leaning over the table toward me with his arms folded.
“I don’t really know,” I say, laughing. “I guess I feel guilty deleting it? Hinge featured me on that San Francisco’s 30 Most Eligible thing, and now it’s like… Hinge is the one dating app I can’t delete, or something.”
“You’re trapped!” He laughs. “I’m serious, though. You’re really pretty. I can’t imagine you’d need a dating app to meet someone.”
“You’d be surprised,” I say, fumbling with my water glass. “I am constantly working. I really don’t have time for anything else. And when I do go out, it’s because I’ve spared time to spend with my family or close friends, or because some company has decided to fly me out somewhere to film something, or some venue is treating me to VIP, or I’m doing some photoshoot for my fans — I don’t really …” My head lulls back and I mock-snore, whining, “I am so tired.”
“Tough life,” he says, teasing me.

But we’re both tired, I guess. Because he travels too, and he loves his job just as much as I love my job, and he saves his spare time to see his family and friends just like I save my spare time to see mine, and we both don’t have time to meet people in the real world because when we should probably be out pretending to grocery-shop so we can run into someone cute, we’re both sleeping instead. Y’know. Because we’re busy.

I almost flaked on him for this date in favor of sleep.
And I would’ve gotten away with it, too, if he hadn’t seen it coming from a mile away.

* * *

After leaving a client’s office around 5PM that same day and snagging a banana from their kitchen, I hopped into an Uber, dropped my head back against the head-rest, closed my eyes, peeled my banana drowsily, and ate it while half-asleep. When I woke up 5 minutes later still in the cab, I had a wilting banana peel in my lap and a half-gulped water bottle (where did that come from?) leaking onto my dress. Ffffuuuu.

Realizing how tired I was, I remembered I had a date, and tried to wriggle my way out of it with a few leading texts.


God damn it.

* * *

“Can we not talk about work?” I ask, waving away the subject. “I’m done with work. No more work-talk.”
“Okay,” he says, thinking quickly. “What’s the last movie you’ve seen?” I burst out laughing at the generic question, and he laughs, too. “That was the first thing I thought of. I know. I’m creative.”
“I actually don’t remember the last thing I’ve seen,” I say, glancing down at the floor, hoping it’ll spark some vague memory of whatever film I may have pulled onto Netflix recently. … Nope. Nothin’. “Wow. Have I really not seen a movie in this long?” I sigh in despair. “I seriously work too much.”
“The last movie I saw was that Alan Turing movie,” he says, “the one with the gay guy, and the computer, and World War II.”
“I SAW THAT ONE!” I say, giddy, feeling like I have a life again. “… On a plane ride during a work trip,” I finish, slumping a bit in defeat, laughing at myself because FML. “But I liked it. I like Benedict Cumberbatch, actually. He was genius in Star Trek.”

Our conversation flows like this for a while. We share a bottle of wine, eat good food, politely push away not-so-good food, and talk about our families, our heritages, our siblings, and what we’ve been up to. That’s what this is, after all; a chance for us to get to know each other; to see if we like one another; to see if the pictures we thought were so attractive on a dating app measure up to the real thing.

“You’re really lovely in person,” he says, reading my mind. He’s holding my hand now, leading me safely over Muni tracks and across the street to this ice cream parlor next door. I’m masterful in high-heels, but what girl doesn’t like being offered an arm just in case?
“Thank you,” I say, unsure of whether to return the compliment or not. On my end, I’m still figuring him out. He’s nice, but … Like my dad always says, boys are supposed to be nice to you. They don’t get special treatment just because they’re being sweet.

When we reach the ice cream parlor, there’s a long line ahead of us.
I guess it’s a popular spot?

“You’re so tiny,” he says as I step up onto the elevated entryway and turn to face him. Standing in front of me, a level lower, he’s still taller than me. And I’m in my high heels.
“Pfft, you’re huge!” I joke, play-defensive.
“How tall are you, again?” He asks, placing his hands on my hips, smiling.
“5’1,” I say, returning his smile and easing his hands away gently. “How tall are you?”
“6’1,” he says. Confident. Grinning.
I roll my eyes at him.

Oh, tall boys.
You’re all the same.

We’re walking down the street now, ice cream in hand, trying each others’ flavors and joking with one another about this or that. He’s boisterous now, laughing louder, having a good time. But he’s also a bit grabby? Which, I mean, is fine because he doesn’t come off as rapey or anything, but …

“On a scale of 1 to 10, 10 being blackout drunk, what are you?” I ask, posing my favorite question for drunk people.
“Why, do I seem drunk?” He asks, pausing, smiling at me.
“Yeah, you do,” I say, laughing.
“I’m a 4.”
“No way. You’re at least a 6. Most likely a 7.”
“No I’m not!” He says, holding his ice cream spoon up defensively.
“You so are! I can tell! Because I’m, like, a 4 right now, and there’s no way you’re a 4, too. Maybe you think you’re a 4 because you’re way more drunk than this on a consistent basis, and so you’re measuring based on your drunk frequency scale.”

We’re both laughing now, and we’ve made our way into some random wine bar in Russian Hill. We order a glass to share, pick at our ice cream, and talk.

“Okay. I’ll be honest. I had a beer before I came to see you tonight,” he admits.
Just a beer?” A likely story. I’m laughing.
“Okay … A scotch. So, two drinks. … And okay, before that, I had a drink with some coworkers –I was nervous!!”
“Nervous?!” I’m cracking up, one hand to my heart, attempting to still the laughter welling up from my chest. “Why would you be nervous?!”
“Well, I’m not nervous anymore!!” He says. “I didn’t know you were so easy to talk to! You never have a shot or something before a date?”
“NO!” I say, still laughing. “And I had no idea guys did that. That’s … That’s so cute.” I’m rubbing laughing tears from my eyes, smiling at him.
“I guess.” He says, smiling back at me, shaking his head.

The night nears that point when it feels like it’s a good time to say goodbye.

“I don’t want you to go home,” he says.
“It’s not like you’ll never see me again,” I remind him, squeezing his hand. We’re standing outside now, and it’s cold out.
“It depends on how busy we both are, right?”
“Yeah … That, again.”
“That again.”
He grins. “Okay. I’ll get you a car.”

When my ride arrives, we hug goodbye, smile at one another, and part.

At home, I tweet:

Boys are so funny.


Then I climb into bed, and go to sleep.
I have work in the morning, after all.

~ Sherilynn “Cheri” Macale

PS. Here’s my “first date” look. Do I look sunburnt?

sunburnt or nah