The 10 Travelers You Meet on Every Group Trip
Birthday Trip, Turks & Caicos
Let’s Be Honest — Group Travel Is a Social Science Experiment
If you’ve ever traveled with more than one friend, you already know: group trips are where true personalities come out. Forget zodiac signs — nothing reveals who someone really is like watching them navigate airports, shared bathrooms, getting lost in a foreign city, and the emotional trauma of splitting a check six ways.
Traveling together is important because it forces everyone to communicate, compromise, and occasionally apologize for things said while hangry. It’s bonding, it’s chaotic, it’s unforgettable — and it’s the fastest way to learn who you’d survive an apocalypse with.
So let’s break down the cast of characters you always end up with on a group trip. If you don’t recognize at least three of these, congratulations, you’re the problem. Or, if you’re like me, you are at least three of these characters yourself.
1. The Planner (a.k.a. The Trip CEO and Unofficial Travel Agent)
Every group trip has that friend — the one who basically becomes a full‑time project manager the moment someone says, “We should book a trip.” They don’t just plan; they initiate, coordinate, and herd the chaotic cats known as your friend group. I often fall into this role… not because I’m that organized, but because I have the travel insight and contacts that can take the trip from ordinary to extraordinary.
This traveler researches every activity within a 20‑mile radius of your destination. They know which tours are scams, which restaurants require reservations, and which neighborhoods you should avoid unless you want a “character‑building experience.” They’ve watched YouTube vlogs, read Reddit threads, joined multiple Facebook groups, and if you’re me, you reach out to your local hotel and tourism board contacts for hook ups and insider tips.
And then the masterpiece. The itinerary. A beautifully organized document where every minute is accounted for. Breakfast? Scheduled. Pool time? Scheduled. A 12‑minute buffer to “wander and vibe”? Also scheduled. They even include travel time between activities because they know you’ll underestimate it and ruin everything.
At the airport, they arrive early enough to watch the sunrise. They glide through security like they’re on a conveyor belt made of privilege because, of course, they have TSA PreCheck, Global Entry, and three credit cards that give them lounge access. They know exactly which card earns 3x points on travel, which one gets free checked bags, and which one has a secret perk like “priority boarding if you smile politely.”
While the rest of the group is eating a sad $14 airport sandwich at the gate, The Planner is in the lounge sipping a complimentary mimosa, charging all their devices, and sending one last reminder: “Don’t forget — we’re meeting at baggage claim. Please don’t wander off.”
They are the backbone of the trip. The glue. The reason you’re not sleeping in a hostel that smells like regret.
And yes, they will absolutely judge you for not reading the itinerary. They spent six hours making it. The least you can do is pretend.
2. The “I’m Just Here For The Vibes” Friend
Every group has that one traveler who floats through the trip like a warm breeze. They show up to the airport and half the trip with nothing but vibes — vibes only. The “just tell me what to book and when to show up” friend and learns about the itinerary in real time as it’s happening. This is the easygoing traveler that you always question if they’ll show up, but know that no matter what they end up doing, they’re having a great time.
This could be the friend who will lean over mid‑flight and whisper, “Wait… where are we going again?” They will ask “What’s the plan?” every 45 minutes, even though the itinerary has been pinned in the group chat for three months. They’re not ignoring it — they simply live in a reality where plans are optional and time is a social construct.
They’re the ones who wander off in the airport because they decided they wanted to go shopping. They’re the ones who show up to a five‑hour excursion wearing flip‑flops because “I didn’t know we were hiking.”
And yet… they have the BEST time. They’re laughing, dancing, vibing, and somehow making friends with locals everywhere they go. They’re the human equivalent of a balloon floating above the group — carefree, unbothered, and radiating main‑character energy.
Here’s the irony: this is secretly where I thrive the most.
Yes, I’m usually The Planner — the one who organizes, coordinates, and keeps the group chat from collapsing into chaos. When I don’t have to plan? I love to show up and go with the flow. I’ve landed at airports I’d never heard of, arrived in cities I didn’t bother Googling, shown up to work conferences without knowing what hotel I was booked in, and once tried to take a taxi to my hotel in Venice like an absolute amateur. The list is long, humbling, and honestly… kind of iconic.
The truth is… I want NOTHING to do with decision‑making. I want to show up, hand over my brain, and let someone else tell me where to be and when. I want to be guided like a toddler holding a leash backpack.
There is something magical about switching off the “trip CEO” mode and becoming the person who just floats along. After weeks of planning, researching, booking, and reminding people to pack chargers, I want to be the one who simply exists. I want to be the friend who says, “Whatever you guys want to do, I’m down,” and actually means it.
So yes — I’m the planner, but spiritually? I’m also the “I’m Just Here For The Vibes” friend. The duality is real.
3. The One Who ALWAYS Loses Something.
Traveling with this person is like being on a scavenger hunt you never signed up for. Their phone disappears before the plane even taxis or every time they take their phone out for a photo op. Their wallet vanishes somewhere between ordering a latte and forgetting to pick it up. Their passport? Oh, that’s off living its own Eat, Pray, Love journey. Meanwhile, you’re becoming a regular at every lost‑and‑found desk on the continent, explaining "again” that your friend “swears they left it right here.”
They spend half the trip retracing their steps and asking if anyone has seen their charger, their sunglasses, their boarding pass, or—on particularly chaotic days—their dignity. They spend the other half of the trip attached to your every move because you are their source of payment, communication, and sense of being for the remainder of the trip. Eventually, you learn to start carrying extra copies of their documents or keep their Apple ID details in a safe place because you know, deep down, they will absolutely lose the originals. And when the inevitable happens, they always say the same thing with wide, innocent eyes: “This is so weird, I never lose things at home.”
Sure, babe. The traveling gods just have it out for you… exclusively while abroad.
4. The Troublemaker (Usually the one who goes to Jail)
Every group has that one traveler who treats rules like gentle suggestions from a distant aunt. They’re the traveler who somehow ends up in places they absolutely should not be. They’ll wander past a velvet rope because “the lighting looked better over there,” climb a monument because “it felt like a viral video moment,” or casually open a clearly locked door just to “see what’s inside.” They’ll feed the animal everyone else is keeping a respectful distance from, hop onto a restricted platform for a photo op, or start chatting up a guard like they’re old friends, only to accidentally insult their entire family lineage. They’re the person who sets off a museum alarm by leaning too close to a priceless artifact, or gets us kicked out of the bar for drinking too much and tried to start a fight.
You blink, and suddenly they’re being “spoken to” by someone in uniform while shouting over their shoulder, “IT’S FINE, I GOT THIS.” They do not, in fact, got this. Meanwhile, you’re standing off to the side rehearsing your “I’m so sorry, we didn’t know” face and wondering how you became the designated adult of the group.
They may not always go to jail, but they definitely collect warnings, stern looks, and “Ma’am, please step back” moments like I collect souvenirs.
5. The Foodie
Every group has that traveler whose entire personality becomes food the moment the plane lands. Maybe they’re the foodie who has a well researched and organized local foodie guide and will drag everyone across the city for a cannoli they saw on TikTok. Maybe they’re the vegan who must research every menu like it’s a college thesis. Maybe they’re gluten‑free and spend half the trip whispering “Do you think this has wheat?” like it’s a conspiracy. Maybe it’s the traveler you must feed every couple of hours before they turn into The Hulk. Or maybe they’re the “ballin’ on a budget” eater who insists on finding “something cheap” instead of the mutually agreed upon spots across the group.
The foodie traveler will debate dinner plans like it’s a UN summit, passionately defend their preferred spot or eating choices, and act personally wounded if you suggest “just grabbing whatever’s nearby.” But you forgive them every time, because whether it’s a fancy tasting menu or a hole‑in‑the‑wall with plastic chairs, the meals they lead you to usually end up being unforgettable — sometimes because the food is superior, and sometimes because the group meltdown over dietary restrictions becomes its own kind of bonding experience. It’s certainly an experience you’ll talk about for years to come after the trip.
6. The Early Riser Who Thinks Vacation Means 6 A.M. Hikes
This traveler wakes up on vacation with the energy of someone who has never known exhaustion. Even if they went out the night prior, you can always expect them to be up before the sun, fully hydrated, SPF‑ed, and already halfway through a motivational podcast. Meanwhile, the rest of the group is clinging to their hotel pillows like emotional support animals. They text the trip group chat at 7:12 a.m. with a chirpy “Rise and shine!” and that’s when you remember to put your phone on “DND.”
They’re the kind of person who believes sleeping past 8 is “wasting the day,” and will proudly announce that they’ve already been to the gym, grabbed coffee, saved pool lounge chairs for the group, and “took a little stroll around the neighborhood” while you’re still trying to remember what country you’re in. They’ll propose a sunrise hike like it’s a casual suggestion, not a threat, and somehow convince you to join — only for you to spend the entire climb questioning every life choice that led you here.
Traveling with them means you will see parts of the city no one else has ever seen, mostly because normal people are still unconscious. And yes, you’ll complain, you’ll drag your feet, you’ll swear you’re never doing this again… but then you’ll reach the top of some hill, see a ridiculous view, and begrudgingly admit they were right. Just don’t tell them that. They’ll schedule a 5:45 a.m. “bonus walk” tomorrow.
7. The Nightlife Enthusiast Who Never Sleeps
This traveler is powered entirely by coffee, adrenaline, and the promise of a DJ set that “you just have to hear live.” They arrive in a new city and immediately know which bars stay open until sunrise, which clubs have the best rooftop views, and which bartenders pour heavy. Within 48 hours, they’re on a first‑name basis with every person who works in nightlife — and somehow also know their last names, childhood traumas, and whether they’re “thinking about switching careers.”
While the rest of the group is brushing their teeth and easing into pajamas, this traveler is slipping on sequins and shouting, “We’re just getting started!” They close down the bar, migrate to the club, then end up at an after‑party hosted by someone named Luca who “has great energy.” They return at 5 a.m. smelling like a nightclub floor, glitter in places glitter should not be, and still manage to show up at breakfast bright‑eyed, ordering a mimosa like sleep is a concept for the weak.
You don’t know how they’re alive. They don’t know either. But somehow, they rally again the next night — because it’s a theme night and we couldn’t possibly miss a cute outfit op,” and apparently, you’re coming too.
8. The Photographer Who Turns Every Moment Into a Photoshoot
This traveler cannot walk ten feet without gasping, “Wait — the lighting is insane right now.” They’ll stop the entire group mid‑stride, mid‑conversation, mid‑existence because a random alleyway suddenly has “major editorial vibes.” They take 100 photos of the same building from slightly different angles, crouching, tilting, backing up into traffic, and whispering things like “Yes… yes… she’s giving.” Every meal becomes a full‑scale production, complete with overhead shots, side angles, and a dramatic pause before anyone is allowed to touch their food and the millennial favorite: a video cheers of our drinks and beautiful smiling faces.
They insist on a group photo every 20 minutes — in front of a fountain, on a staircase, next to a stray cat, inside a grocery store “because the colors are incredible.” They’ll adjust your hair, fix your posture, and tell you to “relax your face” like they’re your personal Vogue editor. I personally love this traveler because I know every moment will be documented and we’ll have incredible photos that give everyone back home “travel FOMO.” They catch all your favorite memories that make the whole trip feel a little more magical while also capturing your best angles that you didn’t even know about.
9. The Overpacker Who Brings Their Entire Personality in a Suitcase
This traveler packs like they’re preparing for a natural disaster, a destination wedding, and a surprise Arctic expedition all at once. Their suitcase is the size of a small hatchback and weighs roughly as much as emotional baggage. They show up at the airport sweating with hopes and prayers that their luggage isn’t over the 50lb limit, but still insisting that “it’s not that heavy.” Meanwhile you watch the check‑in agent mentally prepare for battle. Inside this behemoth is everything: three jackets for a summer trip, six pairs of shoes “just in case,” 10 going-out outfits for a short weekend, a full pharmacy, backup chargers, emergency snacks, and 5 hair tools that requires its own zip code.
They’ll unpack in the hotel room like they’re moving in for a semester abroad, laying out outfits, accessories, and a toiletry spread that rivals Sephora. And while you mock them relentlessly, you also know deep down that when you need sunscreen, ibuprofen, a safety pin, a poncho, or a phone charger at 2 a.m., they will have it. They always do. They’re chaotic, they’re dramatic, they’re absolutely bringing too much… but they’re also the reason the group survives.
10. The Drama Queen
Every group trip has at least one traveler who doesn’t just bring a carry‑on — they bring chaos as a personal item. While the rest of us are out here trying to live our best hot girl summer, they’re busy starring in a soap opera no one asked to watch.
They’re always “dealing with something back home,” which somehow requires a 47‑minute phone call right as the group is trying to leave for the day. They’re rage texting on their phone throughout every dinner. They’re late to breakfast because someone posted something “vague” and they’re seeking clarity. They’re late to the tour because their situationship said “we need to talk” which sparked a full-blown meltdown. They’re late to the airport because a tiny hiccup — like a misplaced lip balm — instantly becomes a crisis that apparently outranks making the flight.
And if they’re not knee‑deep in drama from home, they’re creating fresh drama on location. Suddenly they’re mad at someone in the group for posting a photo where the lighting was bad. Suddenly they’re crying in a bathroom because the waiter looked at them “weird.” They’ll complain about waiting in line “too long,” the food being “too salty,” and the weather being “too weather‑y,” as if your group personally curated these inconveniences just to ruin their day.
But here’s the thing: they’re also the group’s entertainment. They provide subplots. They keep morale high through sheer absurdity. They give you stories you’ll retell for years — usually starting with, “Remember when she lost it because her phone hit 12%?”
Travel wouldn’t be the same without them. Mostly because you’d actually be on time… but also because the trip needs at least one dramatic cliffhanger.
Every Vacation Needs its Full Cast of Characters
Group travel isn’t just about seeing new places — it’s about seeing your friends in their raw, unfiltered, sleep‑deprived glory. It teaches patience, teamwork, and the art of laughing through mild disasters. These personalities, as chaotic as they are, make the trip memorable. Without them, you’d just have photos of buildings. With them, you have stories you’ll tell for the rest of your life.
Traveling together is messy, hilarious, and occasionally stressful… but it’s also one of the best ways to grow closer. Every group needs a planner, a chaos agent, a foodie, a rule‑breaker, and someone who loses their phone twice a day. It’s the Breakfast Club of travel.
And if you don’t know which one(s) you are? Ask your friends. They definitely know.
Instagram vs. Reality—The Part of Travel No One Posts About
The part of travel no one likes to post about
Flight delay on my return home
If you follow my TikTok or Instagram handles @flightsoverfeels, you know I’m usually out here romanticizing travel like it’s a full‑time job. Okay, technically it is my full‑time job. I could talk all day about dreamy destinations, perfect lighting, capturing the moment, and that “look at me thriving abroad” energy. My feed is basically a highlight reel of how incredible exploring the world can be.
But for every glamorous moment I post, there’s an unglamorous one I don’t. I’m quick to broadcast the messy side of modern dating and relationships, yet when it comes to travel, I tend to focus on the magic. The freedom, the beauty, the escape, the growth.
This week, my parents almost canceled their two‑week twentieth anniversary trip because a weather‑related flight cancellation sent everything into chaos. Watching them stress over whether to go at all made me realize something: the unglamorous side of travel deserves just as much honesty as the glamorous side I love to share, because it absolutely contributes to the growth experienced during traveling.
So in honor of transparency, and in honor of them, it’s time we talk about the part of travel no one posts about.
The Truth About Traveling
Travel is beautiful. Transformative. Expansive. It’s the thing people romanticize in movies, write about in memoirs, and curate into perfect squares on Instagram. But anyone who has ever sprinted through an airport, spent the night in a terminal, or eaten pretzels for dinner because everything else was closed knows the truth:
Travel isn’t always glamorous.
Sometimes it’s downright chaotic.
You may see me post a stunning beach sunset, but you didn’t see the eight‑hour flight delay spent sitting on a tarmac beforehand. I’ve shared photos from a lush rainforest, but not of the sixteen swollen mosquito bites that came with it. You’ve seen the fun from a friends’ getaway to Nashville, but not the part where I woke up with a severe back injury where I couldn’t move my body, and I had to figure out how I was going to make it to 6pm for a flight home across the country with a large check-in bag and excruciating pain. Literally fight or flight mode.
And yes, you saw me post having the time of my life in Venice, but you didn’t see me miss my 3:00 a.m. wake‑up call. It was the perfect way to kick off a twenty‑three‑hour travel day that felt like a marathon I never signed up for.
These aren’t the moments we rush to post. But they’re part of the story, and part of the growth I’m always preaching about. The truth is that these messy, unglamorous moments are the ones that shape us. They’re the character‑building chapters that make the beautiful ones feel earned.
The Chaos Behind the Magic
No one tells you that travel is fifty percent magic and fifty percent “figure it out.” But that’s exactly what makes it meaningful.
A missed flight teaches patience, the kind you can’t learn from a self‑help book. It teaches critical thinking under pressure to figure out your next move, which could be a very costly decision. A weather disruption teaches surrender, because when you’re determined to do something, sometimes the universe says “guess again” and there is nothing you can do about it. A reroute teaches adaptability, the kind that reminds you that you’re capable of pivoting faster than a dating app bio. A lost bag teaches resourcefulness, because you can survive with only the items in your carry‑on. Or it teaches you to adapt a new mindset on packing for future trips: “how can I fit only what I need in my carry-on” mentality vs. “how can I fit 20 extra outfits for this trip just in case.”
These moments don’t look pretty. They don’t feel glamorous. They don’t get the likes.
But they teach you, and then they build you.
The Character Development You Didn’t Know You Signed Up For
Travel forces you into situations you can’t control, and that’s where the growth happens.
Eventually, you learn how to stay calm when plans fall apart. You learn how to find joy in the unexpected. You learn how to trust yourself in unfamiliar places. You learn how to laugh when nothing is going according to plan.
And maybe most importantly, you learn that discomfort isn’t the enemy. It’s the teacher.
The chaos becomes the story you tell and laugh about later. In fact, my crazy travel stories mixed with my chaotic dating life became the idea behind “Catch Flights Not Feels” with everyone suggesting I should share my experiences.
Similar to relationships, the inconvenience you experience during traveling becomes the lesson you didn’t know you needed. The discomfort becomes the moment you realize you’re stronger, more flexible, and more resilient than you thought.
The Beauty of Imperfect Travel
Travel isn’t perfect, and neither are we. That’s the point.
The magic of travel isn’t just in the postcard moments. It’s in the moments that force you to breathe, adjust, and try again. It’s in the moments that remind you that you can handle unpredictability, discomfort, and the unknown, and still find joy on the other side.
And sometimes, the ugly moments blossom into beautiful stories.
You lose your backpack in Mexico on the way to your hotel, and a stranger returns it to you, restoring your faith in humanity, and making a new friend along the way. A bus driver no‑showed on a tour to the Cliffs of Moher on my last day in Ireland which would have forced us to cancel the trip, and somehow I became the stand‑in guide for an eight‑hour excursion. One minute I was a tourist waiting for a bus, and the next I was responsible for getting forty strangers to one of the most iconic sights in the country. It was a huge misunderstanding that turned into one of my favorite travel memories of simply winging it. Queen Elizabeth’s wake fell during my trip to England, and I was urged not to go because of closures and flight cancellations. I went anyway and witnessed a historic moment I am honored and lucky to be a part of.
These are the kinds of moments that remind you that travel doesn’t always go according to plan, but sometimes the detour becomes the story.
The truth is that there will always be a reason not to do something. There will always be a warning, a disruption, a closure, a risk. It may not work out. But what if it does? And what if it doesn’t? What if I had gone to England and every excursion really was closed, just like they warned? Maybe that would have been my chance to find something off the beaten path. Maybe I would have wandered into a local pub, the kind where the floors creak and the bartender knows everyone by name. Maybe I would have discovered something I never would have planned.
Travel is messy. Travel is unpredictable. Travel is real.
And it’s in those imperfect moments that we meet the most honest version of ourselves.
How to Embrace Imperfect Travel
If you want to make peace with the messy parts of travel, here are a few things that help:
Leave room for flexibility. Build an itinerary, but don’t marry it. Don’t plan every moment. The best unexpected moments often show up when your plans fall apart or you leave room to wing it.
Expect the unexpected. Delays, reroutes, closures, cancellations. None of it means the trip is ruined. It just means the story is getting interesting. The best thing you can do is stay calm, understand that things happen outside of your control, and getting upset isn’t going to change anything. Take a breath, understand the assignment at hand, and get to work!
Pivot without guilt. Changing plans isn’t failure. It’s adaptability. It’s resourcefulness. It’s character development in real time. If you missed out on something you were looking forward to, understand you can always go back. As if we need any excuse, here it is. Four tours booked and canceled to the Amalfi Coast? Guess it wasn’t meant to be this time. Looks like I’ll be pivoting to try the world’s first pizzeria instead and will need to come back to see the Amalfi Coast.
Look for the story inside the inconvenience. Every chaotic moment has a lesson, a laugh, or a memory attached to it. Sometimes all three. Next time you experience an inconvenience, I urge to you to think about how it influenced or shaped the rest of the trip. Did you learn something new for future travel? Did something so chaotic happen you had to text the group chat at home in real time for a good laugh? During my 8-hour flight delay, my group chat and I started placing bets on the next chaotic step because it was unbelievable how far it went.
Look for the silver lining. Chaotic moments are inconvenient, but it’s important to remember what’s important. You’re safe and you’re alive. Perhaps that thing that didn’t work out saved you money. That flight that canceled kept you safe. Maybe you weren’t meant to go on that tour today, but there are bigger plans for you in the future.
Ask locals for help when things go sideways. They know the shortcuts, the hidden gems, the backup options, and the places tourists never find.
Trust yourself and your gut. You’ve handled hard things before like a messy breakup. You can handle a missed train or a surprise detour. You’re more capable than you think. Similarly, if something feels off, it probably is. Listen to the voice in your head.
Remember that the magic doesn’t disappear when the plan does. It just shifts. And sometimes it shifts into something better. The most important part is that you will likely try something you never would have stumbled upon and that can be the real magic of travel.
Embrace the Unknown
Travel will test you, stretch you, delay you, reroute you, and then reward you. Yet people often get caught up in the drama of the messy parts: the delays, the disruptions, the unexpected detours. They cancel the trip, cancel the day, or miss out on experiences simply because the chaos feels inconvenient or overwhelming.
But here’s the truth: you can’t let the chaos win. Look it straight in the eye and say, “Not today.”
The magic feels different when you’ve earned it. I talk a lot about the growth experienced from solo travel, and the growth feels deeper when it comes from the moments no one posts—the Instagram vs. reality moments. The moments that force you to adapt, stay patient, and keep going even when the journey gets messy. It’s the version of you that comes home a different person than you left it.
The reward is always there. You just have to get through the chaos to reach it sometimes.
And while we may not post about the chaotic moments, they can often turn into the best travel stories.
Exploring a World of Different Flags—and Avoiding the Red Ones
Traveling the world is supposed to expand your horizons and open you up to a world of new cultures and possibilities — but let’s be honest, it mostly expands your awareness of how many types of men exist on this planet. Every country has a flag, sure. But every man? He’s got a whole flag system of his own.
And in 2026, when dating apps have gone global, remote work has turned everyone into a “digital nomad,” and half the men you meet claim they “found themselves in Lisbon,” navigating these flags has basically become an Olympic sport. Which is ironic, because men love nothing more than showing off their flags during the Olympics — chest out, colors on, full national pride. Meanwhile, women are out here creating our own Olympic event: identifying men’s flags they don’t even realize they’re waving. Sadly, our event has a lot more penalties and lot less scoring.
Welcome to Flights Over Feels, where we don’t just collect passport stamps — we collect stories, delusions, and the occasional emotional bruise from ignoring obvious warning signs. Consider this your international guide to romance, chaos, and the flags you’ll encounter along the way.
Exploring a World of Flags
Before we get into the emotional flags men wave, let’s acknowledge something: have you ever noticed how actual countries put intention into their flags? They’re not warnings — they’re previews. Little visual hints about identity, personality, and what you’re about to experience.
Japan keeps it clean and centered — calm, minimal, balanced energy.
Switzerland is structured and dependable — peaceful and neutral.
Brazil is bright and bold — vibrant, fun, full of life.
Canada? Polite, steady, maple‑leaf sweet.
Flags don’t say “beware.” They say, “Here’s who we are — welcome.”
And honestly? I wish more men were the same. Wouldn’t it be great to have a symbol or visual preview of the type of energy or character we’re about to encounter? Don’t get me wrong… every guy has his own personal flag system — colors, patterns, and signals that tell you exactly what you’re about to encounter—if you know how to look for them and read them. They’re there, but they’re not as obvious up front as the countries you visit.
The Green Flags (Rare, Like a Free Upgrade)
Green flags are like spotting a unicorn in the boarding area or hitting the jackpot in Vegas: unexpected, magical, and probably not real. But when they appear? Chef’s kiss.
He packs snacks for both of you. A man who thinks ahead? A man who brings extra? That’s a man who deserves TSA PreCheck. If he’s a green flag? He probably already has it.
He actually reads the itinerary. Not just skims it. Reads it. Asks questions. Offers suggestions. This is emotional maturity disguised as Google Docs engagement.
He knows the difference between “traveling” and “running from his problems.” If he’s in Bali for “clarity,” run. If he’s in Bali because he likes surfing and sunshine? Green flag.
He doesn’t treat flight attendants like his personal staff. Respect is sexy. Always has been.
He charges his devices before the flight. A man who prepares for the journey prepares for the relationship.
He’s curious. Have you ever traveled with a man who travels like he’s back home? Eats at McDonalds and wants to sleep in until 11am. A man who’s interested in exploring other cultures, meeting the locals or eating their food is giving green flag energy.
He already has Global Entry. This needs no explanation. IYKYK
Green flags are the quiet comforts of travel — the little signs that maybe, just maybe, this man won’t become a cautionary tale on your blog. They’re rare, they’re reassuring, and honestly? A green‑flag man is the real upgrade. Not the seat, not the lounge access, not even the free Prosecco — him. And in a world full of red‑flag turbulence, that kind of upgrade feels downright first‑class.
The Yellow Flags (Proceed With Caution, Babe)
Yellow flags are tricky. They’re not deal‑breakers… yet. They’re the “delayed flight” of dating: annoying, but survivable. The ones you have to convince yourself “I’m not settling, am I?”
The warning signs:
He says he’s “spontaneous,” but it means “unprepared.” Spontaneous is booking a last‑minute flight. Unprepared is showing up with no wallet, no plan, and no deodorant.
He insists that hostels are part of the experience. Yes — the experience of being 19. You’re 39. Grow up.
He has a favorite country… and it’s concerning. If it’s Thailand, Colombia, or anywhere with cheap beer and cheaper decisions? Yellow flag with red undertones.
He insists on boarding the second they call Group 1… and he’s in Group 7. Calm down, Maverick.
He says “let’s go camping instead.” Not a crime, but not for me.
He insists on checking a bag. If he packs more than me, I’m not judging. But I have questions.
He says “I’m not really into planning.” Translation: I will be planning.
Yellow flags are the soft warnings — the gentle nudges from the universe that say, “Sweetheart… keep your eyes open.” They’re not red enough to run, but they’re not green enough to relax either. They’re the men who pack too much, plan too little, and somehow make a two‑hour flight feel like a long‑haul. You don’t bail… but you absolutely keep your seatbelt loosely fastened.
The Red Flags (Do Not Board)
These are the flags you can spot from the other side of the terminal. The flags that scream, “ABORT MISSION! Turn around NOW.”
He can’t commit to a date. If he commits to trips like he plans your dates, run!
He posts the trip, but not you. If you’re not in the frame, you’re not in the future.
He says “I hate culture.” He just travels for the McDonalds and hotel Wi-Fi.
He’s chronically “between jobs.” For three years. On purpose.
His opening line on a dating app is “I see you like to travel. Where are you taking me?” Into my “unmatch” file. Next!
He claps when the plane lands. I’m sorry. I don’t make the rules.
He “forgets” his wallet. At the airport. At dinner. At life.
He calls every ex crazy. Usually there’s a common denominator. Spoiler alert: it’s YOU!
He treats the middle seat like a territorial conquest. Elbows out, legs wide, vibes hostile.
He’s rude to staff and doesn’t tip well. Lack of respect gives me the ultimate ICK.
He thinks “digital nomad” means “unemployed but with Wi‑Fi.” Red flag with a side of delusion.
He turns his phone off and doesn’t reach out when he travels without you. Sir, did you attend a silent retreat?
Red flags aren’t subtle — they’re the full‑body shiver you get when the turbulence hits. They’re the behaviors that don’t just inconvenience you… they cost you. Time, energy, sanity, peace. They’re the men who turn vacations into recovery periods and relationships into survival missions. And once you see a red flag clearly? You don’t negotiate. You don’t rationalize.
You grab your carry‑on, keep your dignity, and head straight for the nearest exit — no gate change required.
Learning the Signals
In the end, exploring men is a lot like exploring countries: every flag has meaning. Some welcome you in, some make you pause, and some tell you to turn around immediately. But that’s the fun of it — learning the signals, trusting your instincts, and knowing when to stay, when to wander, and when to book a one‑way flight out of there. Because the world is full of flags… but you only need one that feels like the right destination. Welcome to the life upgrade.
And if all else fails? There’s always the upgrade list as a backup plan.
Most Friends Can’t Coordinate Dinner While Mine Plan International Trips
A celebration of the chaotic, committed, passport‑ready friendships
Most friend groups can’t even agree on a dinner reservation. Someone’s “not doing carbs,” someone else “already ate,” someone’s running late, someone can’t afford the venue and someone mysteriously disappears the moment the words Where should we go hit the chat.
Meanwhile, my friend group? We’re out here planning international trips like it’s our part‑time job. Oh wait, it technically is my job so I suppose it helps when you have one in the friend group always planting the seed.
While other groups are still debating sushi vs. tacos, we’re comparing flight prices, comparing outfits, dropping hotel stay links, and casually saying things like, “Should we just do Turks & Caicos?” We don’t pick a restaurant — we pick a country.
And honestly? I’m so proud of us.
It’s a big enough challenge for me to get a boyfriend to commit to a trip. Actually, it’s just challenging to get a man to commit to plans on a Saturday. These men are clearly part of the other friend groups who can’t even plan dinner.
Getting a group of adults to commit to anything — let alone a trip that requires PTO, passports, and a full itinerary — is nothing short of miraculous. It’s diplomacy. It’s logistics. It’s blind optimism. It’s friendship at its highest difficulty setting.
What’s even more impressive is the diversity of our friend group all being in different places in our lives to come together and make it happen. Some are married long term, some are newlyweds that we’ve known since the beginning of their love story, some are divorced, some are newly engaged and some of us are as single as our passports are stamped. But, it just works.
And when it works? When the trip actually makes it out of the group chat? It becomes the kind of memory that bonds you for life. 📱
When the Trip Actually Makes It Out of the Group Chat
There’s a moment — a sacred, almost spiritual moment — when a group trip crosses the threshold from chaotic fantasy to actual reality. It’s when the group chat shifts from memes and unhinged voice notes to… logistics. Real logistics. The kind that require calendars, commitment, and courage.
It always starts with one brave soul typing the words that change everything:
“Okay, but seriously… are we doing this.”
Suddenly, everyone plays into a role. You have the friend who always asks to go on trips with you but will never commit. They are the ones that watch but go silent. You have the core group that you know will always say “count me in” because we can’t bear the FOMO that will come from missing out on the memories from another international debauchery. You have the friends who are already looking up flights and hotels before we even decide where we’re going and the others who just say “tell me what to book” and just show up.
And then it happens. The moment that separates the dreamers from the doers:
Someone finally books their flight.
That’s the point of no return. That’s when the trip officially escapes the gravitational pull of the group chat. That’s when everyone else has to either commit or admit they were never serious.
If you’re lucky, your friend group has a points guy who travels so much for work that he accumulates the highest level of status and invites everyone on his itinerary to book business class for under $200 per person. If your friend group doesn’t have that guy, start looking for one.
And when the confirmations start rolling in — seat selections, hotel reservations, business-lounge access, passport renewals — you realize something magical:
This isn’t just a trip anymore. It’s a collective triumph.
A logistical miracle. A testament to the fact that your friend group is built different.
🌍 We’re Not Just Friends — We’re a Travel Task Force
Every group has roles, and ours are elite:
The Planner (this is usually me as the Travel Industry hook up)
The Points Guy
The Flight Deal Hunter
The Spreadsheet Queen
The “I’ll Go Anywhere” Wildcard
The Boat Guy (yes, our trips often involve being on a boat)
The Human Yelp Review
The One Who Packs Like They’re Fleeing the Country
The One Who Packs 20 Minutes Before Leaving for the Airport
Together, we’re unstoppable. Separately, we’re… well, still unstoppable, but with less shared luggage.
🧳 We Don’t Just Travel — We Commit
We’ve mastered the art of:
Coordinating PTO like a synchronized swim team
Booking flights at 2 a.m. because “the price dropped $14”
Pretending we’ll wake up early to journal and drink water
Packing all brand new outfits we bought for the trip that we absolutely will not wear but may gift to our trip mates
Fixing our schedules so that we never miss a sunset
Creating itineraries that are 40% realistic and 60% delusion
And somehow, it all works.
Because the moment we step off that plane — sleep‑deprived, over‑packed, possibly over-stimulated and buzzing with excitement — everything clicks. The chaos becomes comedy. The planning becomes payoff. The group chat becomes a living, breathing adventure and our base of sharing the hilarious or oh-so-cute photos we took of each other.
🌄 We Collect Memories, Not Just Menus
Some friend groups bond over brunch. Ours bond over:
Getting lost in foreign cities
Catching boats and daily sunsets
Themed nights and matching outfits for the cutest photos
Laughing until we cry while pregaming in someone’s hotel room
Sharing chargers, snacks, beverages and emotional support
Turning every mishap into a story we’ll tell forever
We don’t just go out to dinner — we go out into the world.
And that’s the difference.
💛 Because These Are the Friendships Worth Traveling For
Anyone can show up for a meal. But showing up for a passport‑stamped, time‑zone‑crossing, memory‑making adventure? That’s a different level of friendship. That’s family.
It’s commitment. It’s chaos. It’s love. It’s choosing each other — not just for a night out, but for a whole experience.
Most friend groups can’t even plan a trip to dinner. Mine plans international trips. And honestly? I wouldn’t trade them for anything. From Newport, to Nashville, to Cabo, to Las Vegas, to Tulum, to London and Paris, to the Mediterranean, to Miami, to Turks & Caicos and the Bahamas, I can’t wait to see where the next adventure takes us and the memories that come along the way.
✈️ Girl Math: The Unofficial Financial Philosophy Powering Women’s Travel Trips
Girls trip to Tulum
If you’ve ever justified a plane ticket because “future me deserves this,” or declared that a hotel upgrade is “basically free” when split four ways, congratulations — you’re already fluent in Girl Math, the playful, logic system that makes travel feel more joyful and a lot less guilt‑ridden.
Girl Math didn’t appear out of nowhere. It grew out of a generation of women where everything — housing, groceries, travel, even basic fun — costs more than it ever has. And let’s be honest—we’re no longer marrying men to help out with our financial situation. It’s our way of saying: If the world is going to financially screw me anyway, I’m at least going to find a loophole to enjoy where I can.
Girl Math isn’t about ignoring financial responsibility. It’s about reframing spending in a way that aligns with how women actually experience travel: socially, emotionally, and with a healthy dose of humor. And honestly, it works.
Let’s break down how Girl Math shows up on female or solo travel trips — and why it makes those trips even better.
💄 1. The Pre‑Trip Purchases That Don’t Count
According to Girl Math, anything you buy before the trip is an investment in the experience — and therefore not a real expense.
New swimsuit? “I’ll wear it for multiple trips and summers to come, so it’s basically free.”
Matching vacation outfits? “Memories and the cute photos are priceless.”
New luggage? “Purchasing a new carry-on saves me time and money from checking in.”
The logic isn’t about denial; it’s about acknowledging that preparation is part of the fun. Women often bond through planning, and Girl Math turns that bonding into a guilt‑free zone.
👗 2. The “Save Here, Splurge There” Equation
Girl Math thrives on balance — or at least the illusion of it. Nowhere is this more obvious than in the way women prep for travel. We’ll hunt down $12 SHEIN dresses, $6 sunglasses, and a $9 bikini set… all while boarding a $10,000 vacation like it’s nothing.
Because in Girl Math, outfits are temporary, but the experiences are forever.
It’s not hypocrisy. It’s prioritization.
Cheap outfits = “I’m being financially responsible.”
Expensive trip = “I’m investing in my happiness.”
A once‑in‑a‑lifetime excursion = “You can’t put a price on memories.”
We want to look good, but we want to feel even better — and that feeling comes from the trip itself. The laughter, the late nights, the beach days, the inside jokes, the photos we’ll scroll through for years. The clothes are just props; the moments are the main event.
Girl Math says: If I save money on the little things, I’ve earned the right to splurge on the big things.
🧮 3. Cost Per Wear… But Make It Travel
Girl Math loves a good cost‑per‑use calculation. On trips, this becomes cost‑per‑memory.
A $200 excursion? If you talk about it for the next five years, that’s practically pennies per emotional return.
A $50 beach hat? If it appears in 12 photos, the cost per Instagram moment is unbeatable.
A new $2,000 Louis Vuitton bag that I’ve been obsessing over? I will be wearing it for life and I saved $400 getting it tax-free overseas! And the stories that will surround this special purchase… priceless. It’s not just a bag, but the bag I got at the flagship, two-story Louis Vuitton store in Paris strolling along the Champs-Elysees.
Travel isn’t just about the activity — it’s about the story you’ll tell later. Girl Math simply quantifies that truth.
👯 4. Splitting Costs = Everything Is Cheaper
One of the greatest gifts of women’s group travel is the communal approach to spending.
A $400 villa split among six friends? “Practically free.”
An upgrade from Garden to Ocean View split between friends? “No brainer.”
Shared Ubers? “Cheaper than staying home.”
A charcuterie board for the table? “Group expense — doesn’t count.”
Girl Math thrives in community. When women travel together, the financial load becomes lighter, and the emotional payoff becomes bigger.
🙋♀️ 4. Investing in Future You
One of my favorite and most-used forms of Girl Math is the art of spending today so future you can thrive on vacation. It’s not delusion — it’s long‑term financial strategy with a side of serotonin.
· Pre‑Booking an All‑Inclusive = Future Me Lives for Free. There is no greater Girl Math high than stepping onto an all‑inclusive resort property and realizing everything is already paid for. Suddenly, every meal, every drink, every poolside snack is “free.” Honestly, I’ve spent less on a week at an all‑inclusive than I have on groceries, gas, and random Target runs at home. That’s not a vacation — that’s financial optimization.
· Gambling for Future Discounts. Is it risky? Sure. Is it Girl Math? Absolutely. If you gamble enough on a cruise or at certain hotels, you can qualify for discounted or even free future trips. So yes, go play that roulette, sis — you’re not losing money, you’re investing in future vacations.
· Loyalty Points: The Girl Math Retirement Plan. Hotel chains and airlines practically beg you to earn points, and Girl Math says it would be irresponsible not to. The more you travel, the more freebies you unlock — room upgrades, lounge access, bonus nights. It’s like a rewards program for being fabulous.
· Travel Credit Cards = Future Flights in Every Purchase. If you’re not earning points on every coffee, grocery run, or impulse buy, you’re leaving future vacations on the table. Travel cards turn everyday spending into flights, hotels, and upgrades. That’s not debt — that’s an investment to future joy.
· Booking Your Next Trip Before You Leave. One of the most powerful Girl Math moves: booking your return trip while you’re still on vacation. Resorts and cruise lines often offer massive discounts if you book before you leave. And honestly, what better time to commit to another trip than when you’re sun‑kissed, relaxed, and convinced you’re moving abroad permanently.
🍹 5. Vacation Calories and Vacation Dollars Follow the Same Rules
Just like vacation calories “don’t count,” vacation dollars operate in a parallel universe.
The $18 cocktail is part of the ambiance and support of the local economy.
The overpriced airport snack is a survival tactic.
Ordering the region’s signature dish isn’t indulgence — it’s research. You’re educating yourself about other cultures. That $28 entrée? A tuition fee.
The souvenir bracelet is a future heirloom.
The rooftop bar is an ROI on excellent photos.
Travel Girl Math says: if it enhances the vibe, it’s worth it.
👜 6. Time Is Money — And Girl Math Values Time Highly
Women often juggle work, caregiving, emotional labor, and social commitments. So when they finally take a trip, time becomes the most precious currency.
That’s why Girl Math justifies:
Paying extra for a direct flight—Bonus Girl Math: If you take the red-eye flight, you pay for one less hotel night and increase your time abroad by having a whole extra day!
Upgrading to a hotel closer to the city center—Bonus Girl Math: staying in the city also saves you money by paying less on transportation if it’s a walkable city.
Booking the spa appointment instead of “roughing it”.
It’s not indulgence — it’s efficiency.
🌍 7. Experiences Are Assets
Girl Math reframes travel as an investment in personal growth, friendships, and mental health.
You don’t “spend” on travel. You gain:
Confidence
Connection
Perspective
Joy
A camera roll full of serotonin
In this framework, travel isn’t a luxury — it’s a form of self‑care.
💖 Why Girl Math Works for Women Travelers
At its core, Girl Math is a playful way of acknowledging something deeper: women deserve rest, adventure, and pleasure without apology.
It’s not about ignoring budgets. It’s about giving yourself permission to enjoy the life you work hard for.
And honestly? If Girl Math is what gets you on that plane with your best friends, it’s worth its weight in gold.