8 of the Most Awkward Travel Scenarios and How to Survive Each

See recent posts by Kyle Valenta

Let's face it: There are almost limitless things that can go wrong when you travel, from financial disasters to getting lost in a place where you don't speak the language. Putting yourself out in the world and exploring takes guts. The risks are, of course, part of the reward, but it doesn't mean you won't find more than your share of potentially awkward or uncomfortable situations while you're traveling. Thankfully, the Oyster.com team has experienced nearly every unpleasant travel scenario under the sun. With that in mind, we've come up with some tips on how to best avoid or handle the most awkward scenarios that you're likely to find when you're out on your next adventure.

1. The Epic Friend Fight

You’re stressed at work — or have been for some time — and a text from your friend comes along begging you to join him or her on an impulsive whim to fly to Europe for a week. You decide to join. But what you may not be prepared for is a little strife. Yes, quality time with a best bud in a foreign country can be an incredible bonding experience, but unless you two spend 24 hours a day together seven days a week on a regular basis, you’re likely to discover some personality quirks that will show themselves quickly when you’re traveling. Epic travel fights between even the closest of people have erupted over everything from where to eat, what kind of hotel to book, and getting from point A to point B. 

So how can you avoid any issues in advance? Set some boundaries before you board the plane. If you need to share a single hotel room, discuss any potential nighttime visitor protocols in advance (and stick to them!). Build in some alone time every couple of days to give yourself some space to experience your chosen destination on your own terms. This will give you both some breathing room and make those nights out together even more fun, as you catch up on all the cool things you’ve seen and done. 

2. The Taxi Ride From Hell

Street at the Renaissance New York Times Square Hotel/Oyster

Street at the Renaissance New York Times Square Hotel/Oyster

Tourists are easy prey for everything from pickpocketing to extortionate bills for food and drink. One of the most famous rackets you’re likely to find in Asia — particularly India — is the taxi or tuk-tuk ride that turns into an impromptu tour of the city’s supposedly most famous silk/souvenir/marble/trinket shops. Alternatively, the driver might suggest that the hotel you’ve booked is no longer open, helpfully offering to take you to an alternative that only he or she knows about. Once you’re inside the vehicle, you unfortunately have little recourse beyond a firm, “No.” And in many cases that will work — but not always. That’s why it’s important to prevent yourself from getting in this awkward situation in the first place. 

Ride-hailing apps can be a useful way around this racket, as the user-review function and readily identifiable drivers make it virtually impossible for a driver to harass their passengers without consequence. However, these services aren’t universally available. If hailing a ride on the street, you should always arrange the fare before entering the vehicle, making clear that you don’t want to stop anywhere along the way. If you’re opting for a taxi service at the airport, always book directly through the official counters, rather than making deals with the drivers who approach you asking if you’d like a cab. 

3. Rampant and Unavoidable Poverty

Havana, Cuba/Oyster

Havana, Cuba/Oyster

It feels almost criminally insensitive to include this on a list of awkward moments, but the truth is that many travelers aren’t quite sure what to do when confronted with desperate poverty in places like India, Cambodia, Brazil, and elsewhere. And the truth is that there’s no easy way to handle this situations: It will feel awkward, you will feel uncomfortable, and — yes — you are partly to blame. The very social conditions that permit you to travel to exotic corners of the world are likely founded on economic systems that have had a role in keeping those impoverished countries’ economies in the gutter for decades (if not longer). 

To be clear, internal economic structures, social policies, and everything from caste systems to nepotism do their fair share of exacerbating poverty — as they do all over the globe. But in South and Southeast Asia — as well as parts of Latin America — poverty and wealth can sit disarmingly close together. This means that travelers are likely to see the two extremes side-by-side. This includes street begging, being approached while eating at tables in restaurants, or while waiting in train or bus stations. Aside from politely declining, or passing a few coins their way, there’s little you can do to cope. It is perhaps worth picking up some books on where you’re going before you arrive to learn a bit about the history and context of what you’re going to see. Eduardo Galeano’s “Open Veins of Latin America” or “Memory of Fire” trilogy are great places to start for Central and South America, while Suketu Mehta’s “Maximum City” is a fascinating window onto Mumbai and India. 

These days, there are developments that may ease some of the guilt for travelers when interacting with people who lack the same means as themselves. Some of these options may even be economically beneficial to the local population. Favela tours in Rio de Janeiro or slum tours in Mumbai are just two such options, though they’re not without their critics who see these practices as exoticizing poverty while doing nothing to remedy the social construct that has led to it. Voluntourism is another way to potentially do some social good while expanding your horizons, though you must do a significant amount of preliminary research to make sure your money and time are actually benefitting the local community and not just some non-profit office workers back home.

4. Eating Alone as a Solo Traveler

The Sea Grape's buffet at Half Moon/Oyster

The Sea Grape’s buffet at Half Moon/Oyster

So you’re thinking of traveling alone. Well, you’ll need to be prepared for a whole host of awkward moments, but — as we’ve already told you on many occasions — the benefits of solo travel vastly outweigh the risks. However, if you’ve never done it before, eating alone can be something that feels a little uncomfortable for many people. If you want a little practice, try doing this alone at a restaurant in your hometown before you attempt your solo-dining skills elsewhere. If that’s not an option, there are a few approaches you can take to ease the stress you might feel about it. 

For starters, aim for the bar or bar-like seating areas in whatever restaurant you’ve chosen, should full menu service be available at the bar. You’re less likely to be the only solo diner. As that’s not always guaranteed, though, you need to be prepared for the likelihood that you’ll be seated at a table that’s far too big for just one person. We’ve found that a reliable Wi-Fi connection and a few hilarious texts to your friends back home is helpful. Alternatively, a good book is always a solid way to divert your attention from any crushing senses of loneliness. That and wine.

5. The Squat Toilet

Outside of North America, the squat toilet isn’t exactly uncommon. Even in the older corners of Western Europe, you may come across this relic. However, they’re far more common in parts of the Middle East and across Asia. There’s really no delicate way to tell you how to use them — simply squat, aim, and hope for the best. The real trick, though, is to keep in mind that toilet paper isn’t guaranteed in many of these types of bathrooms. Instead, pitchers are often provided for cleaning one’s self (this is the reason you’ll see a majority of Indians eating only with their right hand, as the left is reserved for taking care of less-clean functions). If you’re traveling across South Asia simply get in the habit of carrying your own roll of toilet paper or a pack of wipes, plus plenty of hand sanitizer. Alternatively, if you can hold it and search around, you should be able to find a Western-style toilet, particularly if you’re in a big city.

6. You're Not Allowed to Share a Room with Your Opposite-Gender Travel Companion

Depending on where in the world you’re traveling, hotels may not always permit male and female travelers to cohabitate unless they’re married — this often depends on local law. Yet even in places that forbid mixed-gender cohabitation (like Dubai), most hotels will turn a blind eye. But not always. It’s not just countries with religious-informed laws that sometimes enforce these rules either. Travelers to Vietnam have reported issues with trying to land a hotel room with their Vietnamese fellow travelers unless they could prove marriage, due to prejudices against sex work, particularly among Vietnamese women attached to non-Vietnamese men. To avoid any issues, simply check ahead with your hotel if you’re traveling in places where this may be an issue (Dubai, Qatar, other Middle Eastern destinations, some parts of India, and Southeast Asia are just a few places where this may happen). However, in most instances, simply telling them you’re married may be enough, as married couples with different last names are quite common across the world. 

7. Exposing More of Yourself than You Intended

Bathroom in The Hudson Studio at The Standard High Line/Oyster

Bathroom in The Hudson Studio at The Standard High Line/Oyster

We love sexy hotel design, and properties like the Standard High Line in New York City are awe-inspiring sights all on their own (and that’s before you get to take in the views of Manhattan’s skyline from inside). However, for those of us who do not clearly fall into the exhibitionist category when it comes to exposing ourselves, you’ll need to take some precautions. Particularly in cities where high-rise hotels are the norm — and where all-glass architecture is proliferating like wildfire — you’ll want to be careful exactly where in your room you’re undressing (or taking care of other unclothed business). Otherwise, prepare to be putting on a show.

8. You Get Stuck With a Travel Companion Who Turns Out to Be Terrible

While many travelers arrive in a destination with a pre-determined pack or travel partner, solo travelers and backpackers are particularly susceptible to this problem. You see, when you’re traveling alone or are backpacking and running at a more casual pace, you’re far more open to connecting with other travelers. This is due to a wide array of circumstances ranging from potential loneliness (if you’re traveling alone) to bedding down in hostels where socializing is the norm.

The story goes like this: You meet someone or a couple people with whom you click, or with whom you bond out of the necessity to keep your travel expenses lower. The first few days are fun, but then they get throw-up drunk or won’t stop talking about this formerly unknown town that’s been spoiled by tourists. After a few days, this can become grating, at best. Luckily, if you’re bedding down in hostels you have plenty of chances to meet other people and alter your travel plans. This comes in handy on longer-term trips. 

If your schedule is tighter, it may be time to bust out that credit card you’ve been keeping for emergencies to find your own hotel room. To avoid getting in the situation in the first place, never reveal more than your plans for the next day or two until you’ve gotten a better read on the kind of person with whom you’re agreeing to bunk. Once you’ve gotten through a day or two together, simply continue on your way untethered.

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