Here’s a true story: On my honeymoon, I walked up to the front desk of our hotel with a giant smile on my face, still in my wedding dress, and asked if there were any suite upgrades available. There were. And they promptly gave it to my husband’s best man.
That’s how extraordinarily bad I was at scoring free upgrades. It’s also direct proof that getting travel perks isn’t as cut-and-dry as “be nice.” I am nice, dammit. What’s the catch? I asked flight attendants, hotel clerks, Uber drivers, friends, friends of friends. I asked those mythological karmic beings who just cruise around sopping up life’s good graces. (We all know one. They make great travel partners.)
Turns out, there’s strategy involved in getting strangers to do things for you. You’ve got to be nice and you’ve got to speak the heck up. Be it a flight, a hotel, a ride, or a restaurant, you paid for this experience and you should be getting every benefit that you possibly can -- within reason. Here’s how it’s done.
For a flight upgrade, arrive at the airport really early
There are two schools of thought here. One is, get to the airport early and chat up the gate agents. Once you’ve got a good thing going, ask if there are any upgrades available and you may end up at the top of the list. Even if the initial answer is no, they’ll remember you at the last minute should Joe Schmo in first class be indefinitely delayed.
... or really, really late
Second school of thought: Ride the adrenaline high of a mad-dash through security, get to your gate at the last minute, then ask if there are any unfilled seats -- you may be able to claim a no-show’s forfeited seat that way. There’s also a chance the flight is overbooked. You’ll be moved to a later one and can request a first-class seat for the inconvenience.
Volunteer to go on later flights
Along those same lines, when your gate agent announces an overbooked flight -- which hardly ever happens, right -- be the chivalrous passenger who volunteers to wait it out at the bar for a later run. They’ll probably reward you with a first-class seat.
Be loyal to the same hotel chain
As it turns out, loyalty is an appreciated virtue pretty much anywhere you go. That story I told about my husband’s best man getting the Presidential Suite on our wedding night? (A suite so grand it came with an actual grand piano, by the way.) He didn’t even ask for it. He was gifted it because he traveled so much for business, and stayed at that particular hotel chain whenever possible. Do that, and eventually they just start giving you grand pianos.
Be able to say “Well, last time I was given... ”
We’re still on loyalty, but that’s because it works. Not just at big chains, either -- smaller boutique hotels and independent inns often have even more to offer, and a smaller pool of committed clientele vying for their perks. They’ll remember you.
The same logic follows for smaller airports. Rental car companies are more likely to notice that you’ve rented from that chain before, or a lot of times before, and will upgrade your vehicle for no reason other than they can.
Don’t book through third-party sites
I think it goes without saying, but if you book through a third-party discount site, don’t bother asking for anything. That goes for hotels, car rentals, and flights. You’re basically invisible to anyone with any power.
Slip your hotel concierge a $20...
Ah yes, good old bribery. The “$20 trick” is a common piece of Vegas lore that has no reason not to apply at any hotel. Rumor stands, slip a $20 to the desk clerk checking you in and straight-up ask if there are any room upgrades or other deals available. It will go one of three ways: You’ll get an upgrade, you’ll get your $20 back, or you’ll get a “nope, but thanks.”
Tip. Tip everyone, and tip well.
Tip your housekeeping staff, your bellboys, your everyone. If you’re a return customer or have to extend your trip, it’ll pay off. And if a hotel or restaurant does end up with a better room or table -- who are they going to give it to? That crazy old coot in room 7 who never tips? No, silly. It’s you!
Don't ask for things when other guests or customers are around
If possible, don’t inquire about free stuff when other guests or customers can hear you. The hotel clerk, or whoever, knows that elementary school birthday party rules will apply: If they give one to you, they’ll have to give one to everybody.
Always give feedback -- both good and bad
Being honest about your experience requires you to be vocal about it. I don’t think I’m alone in having the instinct to just smile silently and trust that those in charge will know what I’m experiencing and compensate me accordingly. If your service is great, say so. If your hotel room has a funky smell or some doohickey on your flight is broken, definitely say so. Maybe a better alternative is available, or maybe, to make sure you’re a happy customer, the provider will go above and beyond. Complimentary drinks, baby.
If you're celebrating something, tell literally everyone
If you’re celebrating an engagement or a honeymoon or an anniversary or graduation or birthday or literally anything, make sure you say it out loud. To everyone. Hotel clerks, Lyft drivers, bartenders, waiters, flight attendants (especially that lead attendant while you hand them their chocolate). There’s no harm in making conversation, right? And make sure that conversation includes a mention of why you’re very special and deserving of free shit.
Or mention that you’re planning a special event
For example, if you’re vacationing at a winery with your SO and you mention you’re looking for a wedding venue, you can probably expect some nicer-than-usual treatment. If you’re thinking of planning a big anniversary or birthday party at your favorite restaurant, make sure your waiter -- or even better, the manager -- hears about it the next time you’re having dinner.
But don’t lie. THEY KNOW.
Y’all, don’t say it’s your birthday if it’s not your birthday (especially at the airport, where everyone and their mother is looking at your ID). Faking an injury, death, or emergency to get a flight upgrade automatically makes you the scummiest person on the plane. Scummier than the dude who brought on McDonald’s and reclined his seat. And nearly every flight attendant, hotel employee, or wait staff I spoke to said they can tell when you’re lying. Just be a good person, m’kay?