From Swipe to Swoon: The Lisbon Lovah
A sun-kissed hottie, three cocktails, and the boldest night of my life. Hot man alert: this one was worth the razor burn. He kissed my cheeks, stole my breath, and nailed the date (Literally).
Last time on Flings & Other Things: How a hair refresh, a dating app, and a daring plan got me Lisbon ready.
Read on to see where my international swiping takes me.
My flight is delayed, but it’s fine. The conference doesn’t start until noon the next day, so I decamp to the lounge and start swiping through the Portuguese profiles. Time flies, because let me tell you—these men are stunning.
And it’s not just the locals. Lisbon seems to be awash in European gorgeousness. Italians and Spanish men with their sun-kissed skin and devilish smiles. Parisians and Londoners, effortlessly polished in tailored jackets and shiny cuff links. And then there are the Nordic guys—tall, brooding, and straight out of a Viking fantasy novel. Pillage away, gentlemen.
And the backdrops in these photos? They’re not just flattering—they’re aspirational. We’re talking vineyards! Cobblestone streets! Swanky rooftop clubs! These guys don’t just know their angles—they own them.
A few matches roll in, which is impressive given the time difference. There’s a 37-year-old architect (refined, probably reads Proust). A 46-year-old wine sommelier (yes, please—marry me and let’s drink our way through life). A 40-year-old photographer with a smoldering gaze and a scarf situation that doesn’t look like it came off a YouTube tutorial (teach me your ways, scarf man). Even a couple of guys in their 20s, which is great for my ego, but no—this cougar is staying in hibernation. For now.
I savor the tiny circles of faces waiting for me to make the first move, scrolling deeper into their profiles. And then it dawns on me: I’m probably one of dozens of matches these guys have, sandwiched between a neuroscientist who volunteers in her spare time and a yoga instructor who teaches kite surfing in Bali. The stakes suddenly feel absurdly high.
According to the rules of engagement, I’m supposed to message first to weed out the creeps. Fine. But when it comes time to type out my open line, my mind is a vacuous void. I try to think of something scintillating, witty, or at least mildly intriguing. Instead, I land on… “Hi.”
Brilliant. A literary masterpiece. Hemingway would weep.
I send a few of these groundbreaking “Hi” messages and just as I start to overthink whether to add an exclamation point, D finally responds. Thanks, D. Great timing.
After the obligatory “How dare he!” reactions to my news about X, he takes a look at my brand-new dating profile.
D: You need a photo that shows some skin. Everyone shows skin.
Huh. Unfortunately (or maybe fortunately), I don’t have a whole album of dicpics like some people. I review my phone again for skin. Tasteful skin. I settle for a beach shot from a couple of years ago. You can’t see much, but can tell I’m in a bathing suit. No double chin. And my collarbones are on full display. I’ve been told I have nice collarbones.
Then it’s boarding time. I travel economy, because sadly, the requisite billionaire boyfriend has yet to materialize. But do I suffer? Nope, because, as usual, I’m prepared. My seat mates look on in incredulous amusement as I construct my in-flight fortress: travel pillows, blanket, inflatable footrest, and my trusty phone tether (because yes, I once lost a phone mid-flight and I’m not risking another Bermuda Triangle moment.)
Because I’m a germaphobe, the hoodie goes up—my hair’s not touching the nasty airplane headrest. Finally, I stick in ear plugs, slip on travel socks paired with hotel slippers, and finish the ensemble with a padded eye mask that I leave perched on my forehead while I pop an Ambien. (No, I can’t provide a link to that.)
I buckle myself in, making sure the seatbelt is fastened over my blanket so no one disturbs me. Beauty sleep is of utmost importance.
Airplane mode on. If the broadcast system decides to glitch, I’m not going down before my new dating life gets off the ground. I grab my Kindle, navigate to my travel collection (Puck Me Secretly, The Stopover, and my ultimate favorite, Managed), and read until I doze off.
The next morning, touchdown. My phone buzzes back to life, and naturally Bumble is my first stop. A tiny red dot over the chat icon indicates messages await. Honestly, I’m not sure what to expect. Flattery? Banter? Genitalia? Turns out, it’s a mixed bag.
There’s the mundane:
“Hi.”
Groundbreaking stuff. I could cry from the excitement."Hey."
Ah, the slightly more casual cousin of 'Hi.'"How are you?"
I guess boring begets boring?
The creepy:
"Hi. Do you live alone?"
And now we’ve entered the Dateline portion of this exchange…“Hi hottie, I’m just playing with my 11 incher.”
11 inches? Ha. Just an inch short of a ruler. Unmatch.What your kink?
Grammar. Use it correctly, and we’ll talk.
The forward (but less creepy):
"Hi! So what’s a stunning woman like you doing on this app?"
Not 100% sure, honestly. But tell me more about this ‘stunning’ business."Hello, beautiful. I’ve been waiting for your message."
Calm down, Fabio.Hi. If I told you I’m already planning our second date, would that be too forward?
Well, aren’t you ambitious? Let’s focus on surviving the first one.
Interspersed are a few responses in Portuguese. After a quick detour through Google Translate, it’s just more of the same:
“Olá. Como vai você?” (Translation: “Hi, how are you?”)
“Você quer tomar um café?” (Translation: “Do you want to grab coffee?”)
“Você é linda.” (Translation: “You are beautiful.”)
At this point, I’m ping-ponging between Bumble and Google Translate as if I’ve signed up for Dating Beyond Borders. Who has the time for this? I don’t Duolingo. I don’t even separate my laundry. Let’s just agree I’m charming in English and leave it at that.
These messages are starting to feel like I’m sampling a buffet of banality with the occasional side of bizarre. Is this dating? Is this my life now?
Still, I persist. Swipe, type, repeat. If nothing else, this is excellent research material.
I respond to a few innocuous messages, and these conversations bounce back and forth throughout the day. As the hours pass, I start eliminating candidates—red flags? Gone. Weird vibes? Bye. General inconvenience? Pass. Emojis, punctuation choices, and overuse of "haha" are all under the microscope. Dating, it seems, is a lot like editing.
By 6pm, I’ve whittled my list down to three potential dates. I finally make plans to meet M, a Spanish hottie. The deciding factor? His choice of bar: just a few blocks from my hotel. And a must-visit according to a few in-the-know sites, backed up with over a thousand five star google reviews.
M’s charming, well-traveled, and even spent a few months in NYC before settling in Lisbon—a built in conversation starter. And his pics are cute, head tilted just so, perfect smile, Just the right amount of stubble. Tall. Young. But still within the range of acceptability. I swear.
And now, preparation. My hair’s still in tip-top shape thanks to C’s sorcery and frizz-fighting serum. (Don’t judge me for not washing it after the flight, those blowouts don’t come cheap. Plus, I highly doubt I’ll find a stylist who’ll hype up my dating profile while perfecting my color.)
My shower is a multi-step ordeal.Round one consists of the hotel-provided soap for shaving gymnastics. Years of laser, and the hair persists. I contort myself into Cirque du Soleil-worthy poses to get everything, towel off, and then grab my trusty hand mirror for some precision work—only to have its tiny light die mid-check. What is it with me and all my low-life appliances?
Round two: back under the water to rinse off any strays, this time with my own soap—and I finish by practically dunking myself in a vat of matching body moisturizer.
Underwear: Black, seamless, and nice enough. No panty lines, no nonsense. I’ve never understood book heroines swanning around in lace and thongs. First of all, lines. Second, butt floss. No thank you. My Calvins are sexy enough for me, so anyone else will have to deal. Besides, packing for this trip was about priorities (ahem, protection), and new lingerie didn’t make the cut.
Outfit: Cute jeans, cute top, no heels. Makeup: I don’t cake it on—if the night goes my way, M will be getting close. Real close. And I crease. I check my handiwork again. Pores. Ugh. The bane of my existence.
Finishing touches: Deodorant. Perfume (safely in a travel atomizer). Normally, I stick to a light spritz on my wrists. It’s pricey, and I don’t want to stain my clothes or break out, and who really sprays behind their ears? Well, apparently tonight, I do. Wrists, ears, and—yes—between the boobs. This is how far I’ve fallen.
I stick a condom into my wallet, add another and some sex wipes and some extra spritzy stuff into a little black satin pouch I got at some wedding that aptly proclaims “Fly me to the moon.” My bag of wishful thinking.
Lastly, I need to make sure M’s not a serial killer. I send screenshots of his profile to D, and turn on location sharing (though I really don’t know how much good this will do since he is an ocean away). Then I grab one of my Apple Airtags out of my suitcase and toss in my purse. And then I get another out of my wheelie bag and stick that into my shoe–this is so not comfortable, but what’s a little stabbing pain in the name of peace of mind? If M does kill me, I just hope he’ll make it quick and painless.
I scan my room one last time. It’s in decent shape, thanks for the miracle that is hotel housekeeping.
When I get to the bar, M is waiting outside. Our eyes lock, and… wow. He’s good-looking. Like, really good-looking. Just like his photos. (Because let’s be honest, only in books do guys show up looking better than their pictures.) I hold my breath, bracing for that moment where he looks like he might have been catfished.
But no. He smiles, and oh my god, it’s giddying. It feels like my libido, which has been in sleep mode for years, just screeched back into action.
He leans in and kisses both my cheeks in that very European way. And it’s game on.
We get chatting. The conversation is lovely—made even lovelier by the three whiskey-based cocktails that I order. I wish I remembered what they were called, but I guess it’s a sign of how good they were that I can’t. I like booze, and a little social lubricant never hurt anyone.
Maybe that’s why, halfway through some discussion, I do something bold. Terrifyingly bold. “Do you want to come back to my hotel?” The words leave my mouth, and suddenly, breathing becomes optional. Is this what bravery feels like? Or stupidity? How do people do this? In my books, I end chapters with a cliffhanging “Come with me,” (usually in the MMC’s POV), and then we cut to the next scene where she is half undressed.
This? This is real life. There’s no fast-forward button. No perfectly placed fade-to-black. We have to navigate the whole awkward lead-up. Wonder of all wonders, he says yes, and doesn’t make it seem leery.
I blurt out, “I haven’t done this in a while.” Translation: never. Does that make me sound like a mess? A bad lay? What if he backs out now? Why didn’t I wait until we finished our drinks to say something? But he’s unfazed. Nice about it, even.
When the time comes, he pays the bill—despite my offer to split it. (Don’t worry, there’s a whole protocol for paying on dates saga coming in future episodes.)
We leave the bar and head back to my hotel. We don’t hold hands. Not that I expected to. Because that would be weird. Holy shit, am I really doing this? It kinda feels like I’m outside of myself watching two people get ready to do the SEX.
We walk into the lobby and the attendant nods at me. He doesn’t say anything to the guy. I keep feeling like he’s judging me. Then I remind myself that he probably sees this stuff all the time and can’t care, but I’m still glad that the elevator comes quickly.
Then we’re in my room. The bathroom light’s the only illumination, just as I planned. Anything more would only highlight the flaws that many years of marriage allowed me to ignore. The air is faintly scented with my Caudalie Beauty Elixir Mist, generously spritzed on the pillows beforeI left. Strategic ambiance? Check. Execution? Uh…Pending.
Because then… I just stand there. What now? Should I say something? Make a move? My brain is cycling through every romantic scene I’ve ever written, and all I can think is: Why am I not better at this?
Luckily, M doesn’t wait for me to figure it out. He steps closer and—praise be—takes the lead.
He kisses me, and not the "meh, this is fine" kind of kiss. No, this is full-on movie magic: hands cupping my face, pulling me in, and suddenly, I’m not worried about what to do anymore. He’s got this. Oh, he’s definitely got this.
Afterwards, he asks to use my bathroom, and leaves. No lingering, no weirdness. I revel in the lack of drama, the sheer efficiency of it all. I get back into bed and lie there, still in shock.
Oh. My. God. That. Was. AMAZING! Like, all-caps, bold, italicized, exclamation-pointed AMAZING. All the type treatments I’d never use in my books, but for this? Absolutely warranted. YES to all the embellishments. It was everything I could’ve wanted and more. Did I already say Oh my god? Well, I’m saying it again.
I bask there with the stupidest smile on my face, and all I can think?
#Winning.
Next time on Flings & Other Things: Back in NYC, I’m swiping with Lisbon-fueled optimism.
Spoiler Alert: it doesn’t last.