🌈 Pride 2023 #1: Miles

As a gay man, I am uniquely qualified to provide these details

For the last few years, I’ve celebrated Pride month at Stripe with a special month of notes. It’s nice to kick off the summer with a little bit of serendipity and something that deviates a bit from my usual brand of writing.

The flag pole bracket that the previous owners had screwed into the tree had fallen off, so I rigged up the apparatus that you see here in order to get the flag up in time without damaging the tree. This DIY project sponsored by Milwaukee tools.

This year I’ll be revisiting some of the themes from the past couple years and introducing some new ones. I hope you enjoy.

Miles

At essentially every airline, you can earn (and/or buy) loyalty “miles” that can then be exchanged for all manner of perks and travel. Travel is a cornerstone of the modern gay man’s lifestyle, and so I’m here as a figurative expert to explain what you can use the miles from each airline for.

Southwest

I have no better analogy for Southwest than “the Trader Joe’s of Airlines”. You’ll almost certainly get to know your flight attendants in the same way that you don’t want to get to know your Trader Joe’s cashier, and they manage to do everything just a little bit differently.

One of my partner’s favorite aspects of flying Southwest is the first-come-first-serve parts of the experience. Check in exactly 23 hours and 59 minutes before your flight for…well, something. When you arrive, you get to stand your ground in line to get on the plane, marking your earliness with your carryon bag at the front of the numbered queue.

For every 1,000 miles you accumulate, Southwest’s gate agents will look the other way as you shove past another passenger to get a lower boarding number. For 5,000 miles, if you’re at the front of the line, they’ll actually let you onto the plane before boarding officially starts. For 10,000 miles they’ll break out the good snacks that they only serve on flights to and from Hawaii.

Frontier

Truly the budget option, Frontier is the choice of the homosexual with way too much PTO and not enough cash to fly American for a long weekend in PVR. Packed in like sardines with an astounding 239 other passengers on an Airbus A321neo, you get to enjoy the comfort of the thinnest seats on any other jet in North America.

For 10,000 miles, you don’t need to worry about sneaking that needlenose pliers on board: Frontier will disable the smoke detectors for you when you use the bathroom. If you open a credit card with Frontier and spend $1,000, they’ll include a safety instruction card in your seat back pocket.

Alaska

Pretty much across the board, folks seem to have good experiences with Alaska. The planes are comfortable, the flight attendants are very nice, the service is adequate. Despite its name and (potentially problematic?) indigenous mascot, the company has been headquartered in Seattle since 1953.

That hasn’t stopped Alaska Airlines from keeping up the Alaskan theme, though. For 20,000 miles they’ll let you fly over Sarah Palin’s house so you can see Russia. For the real adventurer/American, you can spend 150,000 miles for a weekend-long getaway shooting wolves from a Southwest helicopter.

Delta

Lots of people enjoy flying Delta. It’s a great choice for business travelers and people obsessed with their airline status. Delta Medallion status sits just above Crossfit and below veganism in the ranking of things you’ll be sure to learn about someone.

For a clean 50,000 miles, you will receive assurance that they won’t throw your pet’s carrier when loading it into the cargo hold. For 75,000 miles, they’ll try to make sure they still have food options available by the time they get all the way back to your row.

Spirit

Nobody chooses to fly Spirit because they want to. Traveling Spirit is a compromise you make with yourself. And folks who value their vacations more than personal comfort—or who have medications they can rely on to avoid remembering travel on Spirit—will find themselves with miles on America’s least favorite airline.

You can redeem 30,000 Spirit miles to be booked on a flight where the pilots receive regular drug tests. For 50,000 miles, the flight attendant will give you free beverages, but loudly announce it to everyone within earshot. For 70,000 miles, the flight attendant will instead pretend to run your card.

JetBlue

When I fly JetBlue, it gives me the same vibes that a cell phone kiosk at the mall gives. There’s a lot of fun colors and it seems like it’s going to be very modern and trendy, but then the machine runs out of ink when it’s printing your boarding pass and you have to go stand in line and get yelled at because the ticket was booked under “Matt” instead of “Matthew” like the barely-above-minimum-wage TSA employee gives a flying fuck¹.

For 15,000 miles, JetBlue will give you a copy of the in-flight safety video on a flash drive to enjoy any time you like. For 30,000 miles, they’ll turn the wifi off and back on again for you when it stops working immediately after you pay for it.

Virgin

Virgin is a cool brand. Very premium. Virgin is what JetBlue wants to be so badly. But alas, you’ll take your incredibly comfortable flight from the lone Virgin gate in a disused corner of some terminal that time has forgotten. You’ll enjoy an authentic Tom Hanks experience before you settle in under the soft indigo lighting of the plane while the MDMA from the music festival wears off.

Besides the usual perks for miles, 5,000,000 miles will get you a flight on Virgin Galactic. Note that this does not cover the flights to and from Spaceport America in New Mexico—you can use more miles to book that (hopefully round-trip) flight.

For the dedicated Virgin flyer, you can save your miles to earn Triple Branson status. Besides free booze, you’ll get access to the cockpit and a private bathroom stocked with condoms.

United

Other than Air Canada, which is a delight, United is perhaps the only Star Alliance member airline that most Americans will ever fly. There’s nothing really all that special about United, frankly. If you’re flying to SFO, you’ll probably take United and immediately forget the flight afterward because it’s so…adequate. Hell, they even decided that the swoopy-U logo they adopted in 1974 was too spicy and adopted the generic-globe-that-looks-like-an-IKEA-lamp logo that Continental had left over after their 2010 merger.

While there are no secret perks to United miles, the more miles you use on a flight, the lower down on the list you’ll be for involuntary deplaning. If you put up 5,000 miles (or apply for a United credit card) they’ll guarantee you won’t be knocked unconscious by a security officer.

American

The history of American includes shiny, unpainted planes that just look like you’re going to absolutely roast when you get on-board. American has the most hubs in America (10!), servicing amazing tourist destinations like Charlotte, NC and Phoenix, AZ.

With a paid membership, you can get access to the Admiral’s Club. However, with AAdvantage miles, you can get access to the Flagship Lounge. With both AAdvantage status and Mileage Plan points (through the Alaska partnership), you can get access to the Armada Lounge.

With Mileage Plus status and an Admiral’s Club membership, you can get complimentary access to the Navigator’s Helm. Those of you who have Platinum Pro and MVP Gold 75K can enjoy a weekend retreat in the Aeronaut’s Resort. Concierge Key members with five years of earning 500,000 miles each year may be inducted by invitation to the Fraternity of Jetsetters at an undisclosed location.

Pride month roadmap

Some tentative plans I have for the remainder of the month:

• Pride horoscopes

• A ranking of my motorcycle helmet covers by gayness

• Designing drag personas for startup founders

Let me know what you want to see in the comments.

1. I’m not bitter