How to navigate a complicated world, one near-miss at a time.

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Q: Should I tip my flight attendant if I order a drink?

This is a matter of some debate. I was told years ago that tipping your flight attendant would result in, at least, attentive, happy service, and at best, free drinks. I tried it once, and it worked! I got a big smile and a free drink. Then I tried it again on a different flight, and had a situation not that different from The Time I Tipped Someone In China, which to this day remains one of the most excruciatingly embarrassing moments of my life.

According to Taylor Garland, spokesperson for the Association of Flight Attendants-CWA, you should not offer gratuity. “Most airlines have a policy that doesn’t allow Flight Attendants to accept tips,” he told R&K over email. However, off the record, others said that most flight attendants are trained to accept a tip if the flyer insists in order to avoid causing a scene. Because tipping has the potential to be extremely uncomfortable, it’s best to color inside the lines. Offer enthusiastic thanks and smiles instead.

Q: I’m traveling through Tuscany this summer and am planning to propose to my boyfriend. I’m looking for a restaurant off the main tourist circuits where I could pop the question. Any favorite spots?

Bold move with the under-the-Tuscan-sun-style proposal, but I like it. (Have I mentioned my husband proposed to me in a pizza joint in Brooklyn?) There’s really no want for romantic little spots in the region, but I’m particularly fond of Ristorante Osteria del Merlo, nestled in the bottom of a historic church in the tiny town of Cetona. It’s the sort of place where you can sit outside along the town’s piazza and eat the most luscious, tiny lamb chops of your life while drinking beautiful wines from around the country while locals argue over grappa in the corner. By the time they plunk down a bottle of limoncello at the end of the meal, pretty much anyone would be ready to say yes.

Q: I was on a 12-hour plane ride next to a very chatty guy. You know who I’m talking about. He talked to me about his first and third ex-wives, his job as a salesman, his fantasy football team. Tried opening the in-flight magazine and putting on a movie but he just kept jawing away. On and on he went halfway around the world. How do you defuse a dude like this without being a total asshole?

One’s first defense is always to try very obviously putting on headphones. There is a special place in hell for people who do not respect the headphone rule: headphones mean no talking. Even if your headphones are clearly not even plugged into a device, they are the equivalent of a Do Not Disturb sign.

Once someone has crossed this line, you’re basically forced to have a mildly awkward social interaction, so steel yourself. Very politely, turn to the person after the next interruption and explain that you’ve enjoyed chatting, but you reserved this time for work/catching up on sleep/watching porn/whatever. You paid good money for the privilege of sitting in this recycled-air box contemplating the possibility of your untimely and horrifying demise. As long as you do so civilly, requesting time to yourself is not rude. If your seat mate decides to be insulted or makes you uncomfortable—or, if the person is being so chatty because they are visibly intoxicated—you can also approach a travel attendant and request to be moved to another seat. That might feel like a nuclear option, but remember, this person is imposing on you, not the other way around, and you’re probably never going to see them again. Except that you’re locked in a floating prison with them for X number of hours, of course. Other than that, never again.

Q: I’ve been with my boyfriend for two years now and we’re planning a two-month journey through Asia. We’ve done a bit of traveling before, but always weekend trips and short getaways. This will bet the first big international trip together and he seems to be totally ready to go, but I’m a bit frightened. We have trouble deciding on movies and take-out. How are we expected to manage travel snafus in Laos and Cambodia together? Any advice on how to plan this so we don’t murder each other?

My husband and I did some serious scrapping early on in our travels, as is, to a certain extent, inevitable. But after many early mornings, late nights, and fender benders, we came up with a simple motto that has proved extremely helpful: be on a team with me.

Be on a team with me. It sounds simple, but it’s a powerful mindset to have when pitted against the slings and arrows of travel, especially international travel. You’re going to be frustrated and confused, but rather than seeing your partner as the source of your problems, think of them as an ally in overcoming them. It really is you against the world. When your partner is lagging behind with an oversized bag, help him cross that finish line. When he blocks you from getting the tasting menu that is only available for two because he doesn’t eat pork, think of all the times he’s had bread for dinner so that you could try the ribs. Remind yourself, as that initial wave of anger begins to crest, that you’re going to get through this together or not at all; also, that this is their big vacation just as much as yours. Teammates don’t hide their flaws from one another; they evaluate their strengths and weaknesses and help each other compensate where needed. And when you and your partner begin to forget this motto—which you will! It sounds obvious but I guarantee it is NOT at 4 a.m. on a bus in Bucharest!—and begin to blame one another and point out what could have been done differently, say it again. “Be on a team with me.” It’s a very hard request to refuse when you care about someone. If it’s not, find a new team.

Q: I travel a lot for work, and while I’m not very wealthy, I’d like to splurge on something to make my travels a little easier. If you were picking one high-end gadget to make long-haul travel more bearable, what would it be?

Very few travel gadgets are worth anything at all, and a few are downright irritating in their uselessness. (I’m looking at you, airplane cocktail-making kit. Drinking on planes is for survival, not pleasure.) But one indulgence I’ve grown to love is a pair of high-quality, noise-canceling headphones. I never realized how much of my discomfort while traveling was due to the low-frequency hum of most modern modes of transportation. It’s like the entire plane is an anti-human whistle. Most headphones provide a certain amount of passive noise cancellation—meaning covering your ear with pretty much anything blocks some noise—but an active cancellation system, which actually interferes with sound waves, is particularly helpful for the insanity-inducing buzz of a train or plane.

My favorites are the price-y but fantastic Bose headphones. I prefer the earbud style, as this makes them easy to throw in any bag, even for a very short journey, while still providing a lot of sound reduction. Other travelers prefer the slightly better noise-cancelling abilities of an over-ear headphone, but I find the tradeoff for bulk not worthwhile. However, a friend and frequent traveler raves about this wireless version, also from Bose. That’s a serious investment, but if you have the money, they look pretty awesome and people flip out over them.