Two Award Booking Requests Where I Failed to Deliver and One Where I Refused to Help

I’ve been offering an award booking service since 2009, which has booked several billion miles worth of premium cabin awards at ‘saver’ or ‘low’ levels.

It’s grown a lot since I first got an email where, instead of offering just advice I offered to actually make a booking for a fee (the customer was thrilled enough that they wrote to Conde’ Nast Traveler about the experience, and their letter was printed, I was off to a good start — and Conde’ Nast has listed me as one of their World’s Top Travel Specialists each year since 2010).

In fact I have a partner in the business now who has earned tens of millions more miles than I have in his frequent flyer career — and enlisted the help of disabled Thai rice farmers and New Zealand college students to do it.

I like to think I know a decent amount about booking awards, and can come through even on some of the most challenging requests. But there are some things that I Just. Can’t. Do.

Israel, Departing on El Al on the Sabbath

A family of four e-mails wanting to go to Israel in business class, just a roundtrip New York to Tel Aviv. Straightforward enough.

Except that they have two very specific requests.

  1. They want to fly El Al. If they’re going to go to Israel they “want the experience to start right away.”
  2. They want to maximize their time, since vacation days are limited. They have to leave after work on Friday, and return on Sunday a week later.

They were actually pretty flexible on which weeks they’d travel, but those two things were their non-negotiables.

Now, there are many things that I can do with miles and points. But causing El Al to depart New York on the Sabbath is not one of them.

I offered the family connecting flights on Lufthansa in business class. They decided to rethink their trip instead.

Australia for a Family of Five in First Class

The first thing to understand is that Australia and New Zealand represent among the toughest frequent flyer awards. This family wanted to travel during the December/January peak of peak season for that award.

They were a family of five, and they would only travel first class.

At the time it was fairly easy to find business class seats on Virgin Australia (such as Los Angeles – Brisbane, using Delta miles that can be transferred from American Express).

Much of the time clients have to route via Asia in order to get award tickets at peak times. Sometimes that’s a deal-breaker, it’s a lot of extra flying. To others it’s a great opportunity for an enroute stopover.

Getting five seats though? Outside of a fluke (such as an airline accidentally making more award seats available than they intend, United once opened up their entire front cabin to Sydney as saver awards), it’s highly unlikely I’d be able to satisfy the request for first class direct flights between the U.S. and Australia. The only way to do it is extra mileage awards.

I couldn’t offer them first class saver awards non-stop for five passengers. But the first time I visited Randy Petersen‘s ‘House of Miles’ (office, on ‘Frequent Flyer Point’) in 2002 I saw a sign in the training room advising staff never to say “no” and instead to respond, “what I can do for you is…

So I managed to scare up four business class non-stop award seats on a single flight. They could split up and take two different flights or they could buy a fifth ticket. The client’s response?

You see? I knew these miles were worthless.

Sometimes, despite my best efforts, I do fail. But I also don’t ever want unhappy customers, which is why payment is always what comes last and we don’t charge a fee unless we can meet mutually agreed-upon criteria. In both of these cases, I couldn’t.

One Award I Refused to Book

Several years ago I was contacted a woman’s travel roundtrip in business class to Iran, and just a one way to Iran for her 8 year old daughter.

There was no way I’d ever get the full story. What’s the most innocent explanation I can think of? Maybe the father was going to bring her back to the United States — a roundtrip ticket back to Iran for him, a one way ticket for his daughter.

I wasn’t comfortable helping a woman drop off her 8 year old daughter in Iran and leave her there. I couldn’t stop her from doing it of course and maybe she didn’t need to be stopped but I didn’t have to be a part of it.

Not Everything Works Out

We’ve had thousands of successfully booked awards. Things aren’t as easy as when I started. I once helped a family of 7 fly together non-stop roundtrip in Lufthansa first class. Getting started booking awards during the Great Recession with airline premium cabins empty and award space plentiful made it seem like this would always be easy.

Now it’s harder work, and there are more tradeoffs. Sometimes all we can offer are connections and a passenger will only fly non-stop. My job is to explain the tradeoffs and help a client make an informed decision. And my job is also to know when I can’t (or am not comfortable) helping someone and be straight with them about it up front.

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. […] Award booking services are a great service for people who don’t know how to use their points effectively. I used them when I got started and when I saw what was possible, it opened up a world of new opportunities. On View From The Wing, Gary writes about what it’s like to run a booking service and how he’s not able, or in one case not willing, to fulfill every request he gets. […]


  1. Can you give me an estimate for five PAX to Australia, Fiji, back to NYC, EWR in F for 5, or 2 in F, and 3 in J Dept June 5-8, returning 6 weeks later. Would around the ATW be best? Have point banks with Chase, and Amex. AARP Member, prefer non US carriers.

  2. There could be a million reasons a parent wants to book a one way ticket for the daughter. Assuming that because they are going to Iran she is being abducted is purely racist. Only former Iranian citizens can travel from the US to Iran without being part of a tour. So the mother was taking her daughter home. It shows a lack of capacity to understand other cultures to assume otherwise. This type of xenophobia and racism is actually not a legitimate reason to turn away business. Just because you aren’t a public utility doesn’t mean you need to be a racist.

  3. Maybe you could wander over to r/awardtravel and help out the idiot who posted the day of the missile attack, and again yesterday, of her desire to have a relaxing enjoyable holiday in Iran. She’s not dropping off a kid so you should be all set. Personally I hope you can help her get there, and stay.

  4. I guess you are trying not to actually advertise your service but just out of curiosity can you tell us how much you charge?

  5. (I’ve got it bookmarked, but haven’t used the service yet.)

    We charge $199 for each roundtrip (with 1 stopover) ticket booked. One way awards are $99.
    Multi-City awards are quoted separately based on number of stops and routing complexity
    Voluntary changes after booking finalized are $90 per one way, plus any applicable airline change fees
    Voluntary cancellation after booking finalized are $90 per award, plus any applicable airline cancellation fees

  6. Thanks for sharing those anecdotes. Makes total sense, but I was not specifically aware you had that award booking service. I’m sure it’s a fun challenge most of the time, but some of those requests (and expectations) border on ridiculous..

  7. I once tried to use Gary’s service and I think whoever I worked with I made crazy with my indecisiveness and moving target of a schedule. What I can say is Gary has always been generous with his time in helping me know where to look.

    For me, it works out because there always seems to be a last-minute option available. you just need to have patience and flexibility.

    Thank You, Gary, for always responding and helping when I need ideas.

  8. The fact that you got to the point of 4 biz class non-stop seats to Australia in peak timing is pretty amazing

  9. @Emma you must be quite happy you got to call a white male boomer a racist today! Good for you. But you’re an idiot. I live overseas in a country with draconian child custody laws. Kidnapping children as a result is a real and serious problem. In this case it just happened to be Iran. I didn’t read any racism into Gary’s actions.

  10. Wow pretty cool. I don’t always agree with your posts but great insight into how booking works. I’m not really sure of the first example but I know five to Australia first class is a little like winning the lottery!
    @emma. Really? I mean REALLY? I had to double check the news. Unless I missed it nobody made you the xenophobe racist police. Go away

  11. Just keep doing what you’re doing Gary, some people just don’t understand how all of this works. They all assume that if they have a million miles with an airlines, they could get 5 first class seats at anytime lol.

  12. Lately I’ve become leery of helping friends and family book flights since their demands are typically hard to fill…and I’m nervous supporting them if things go awry. I may just hit you up booking a fairly tame itinerary simply because you’ll continue to help if changes are needed or are forced on us by the airlines. Worst of all you have to keep up with the changing landscape with airlines and alliances/partnerships. Totally worth $199 for me to not have to figure all that out!

  13. Belinda,

    The refusal to accept the business of the customer was based on his buying into a racist stereotype.

    If your most local gun shop refused to sell guns to a “white male” just because of the stereotype that mass shooters are “white males”, wouldn’t that be a racist refusal to do business?

    If your local store refused to do business with “black teenagers” just because of the stereotype that “black teenagers” may be shoplifters, wouldn’t that be a racist refusal to do business?

    If your local travel agency of sorts refused to do sell tickets to “Asian female” traveling alone with a “younger Asian female” to Florida because of the stereotype that “Asian females” are sex trafficked into Florida, wouldn’t that be a racist refusal to do business?

    The answer of those wedded to their own racist prejudices is likely to be to deny racist behavior as being racists, but don’t let me get in the way of you defending whatever questionable behavior you want to defend.

  14. @Emma

    “Assuming that because they are going to Iran she is being abducted is purely racist.”

    “It shows a lack of capacity to understand other cultures to assume otherwise.”

    Emma, given your deep and extensive capacity to understand the nuances of other cultures, I’m sure you are well aware that Iran is approximately 97% white, that the caucuses region in Iran gives us the name “Caucasian” and the word “Aryan” is from the Old Persian “Ariya” meaning a Persian (Ultimately from Sanskrit arya – “compatriot”).

    So I’m curious why you automatically assume that just because this woman was engaged in some possibly (but not certainly) suspicious behavior, that automatically means she was a minority? Maybe you watch too much Hollywood? In real life, assuming that that all suspicious actors are minorities is considered … racist.

    I suggest you perhaps watch more foreign films, which typically give a more balanced view of human nature than American movies, and perhaps consider desisting from labeling other people “racist” until you have raised your own consciousness. It’s up to all of us to make this world a better place for everyone!

  15. My family of five did first class on qantas to Australia from lax over two nights the week before Christmas last month. Qantas had up to 4 seats available per day. Quite astonishing lol

  16. SeanNY2,

    Most Americans and others view Iranians as “brown people”, just like with most Indians from India.

    And US CBP definitely tends to view Iranians as likely to be non-“white” whenever CBP is out on its racist profiling bandwagon and has Iranians in particular in scope.

    The idea that Iranians on average are “white” or “Caucasian” like Europeans is a canard. It’s like saying that Arabs can’t be anti-Semites when we are using anti-semitism to refer to anti-Jewish dispositions. Everyone and their dog can yap that Arabs are Semites, but it doesn’t mean that some Arabs can’t be anti-semitic.

    A Caucasian of sort being racist against a Caucasian of a different sort is possible. And by the way, Iran is a multiethnic country, and there are some non-Caucasians there too. Or do you now want to say that Iran’s Arab and African minorities are Caucasian just because they have Persian names at times or that it was unlikely that the Iran-bound customer was anything but fully Persian?

    For all we know, unlikely as it is, perhaps the person wanting to go to Iran was a Persian Jew. That doesn’t mean a Jewish European-American’s refusal to do business with the Iran-bound person can’t still be racist.

  17. Gary,
    Great story! @Emma and @GUWonder, just wondering how you both vould pull away from CNN to post a comment, perhaps time to take a Xanax and watch some puppy videos.

  18. David Szerlag,

    It sounds like Xanax and puppy videos are your thing. Glad to hear you find them so helpful.

    TV isn’t my thing, but cutting into the arguments relied upon to try to justify racist profiling and other racist behavior is my thing.

  19. @GU . So envious of your life task being one who can identify and call out racist behavior but perhaps before considering oneself an expert you should purchase a Webster’s dictionary and understand what the definition of racist is: a belief that race is the primary determinant of human traits and capacities and that racial differences produce an inherent superiority of a particular race. No one apparently except you believe that Iranians fall into a “brown race”, and your comment about CBP is just ludicrous, perhaps some proof of how CBP “profiles’??? Iranians are Persians and are of the caucasian race. Last time I checked Gary was as well. So please get educated and leave your holier than thou attitude at the jetway before you spout off about other people’s motives or beliefs’

  20. Gary,

    What’s your defense to being called out as a …….. “boomer” (by Belinda)? Beside being in your mid-40s and not from the late ’40s. Next thing you know, it’ll be Belinda saying your action is being criticized because you’re a “white male grandpa”.

    Oh, “white male boomer”, I already know your defense about refusing to help the Iranian mother take her daughter to Iran using miles. Not that I will buy it as being a sign that you didn’t operate upon a nasty stereotype when refusing to do business with that woman.


    Thank you for your strident defense of the most subjugated group in America, “white male boomers”.

  21. I’ve used the service many times and it is excellent. Saves me time and I know all options have been considered. I also realize that using award points often means one has to compromise on some things (routing, change of planes, etc) but it’s cheaper than paying for biz class and on international flights that’s the only way to go.

  22. David Szerlag,

    Your cherry-picked definition is not the only one out there for what is racism and racist.

    Iranians are generally viewed in your neighborhood as “brown” in much the same way as Arabs and South Asians are viewed as “brown”.

    Gary is of a different ethnic background than most Iranians and he is not Persian. In that way too your “Caucasian” defense falls on its face, just like the defense that Arab anti-semitism isn’t possible because Arabs are Semites and Jews are Semites.

    Iranians are not all Persians. Persians are just the large majority of Iranians, but there are Kurds, Baluchis, Arabs, Afghans, Armenians and others who are Iranian without being Persian. Iran is a multi-ethnic country, as shouldn’t be surprising given the history of empires in the world.

    CBP does engage in racist profiling. Iranian-Americans, including young children, again learned that the hard way this month.

  23. Of course I must have missed your overtly correct definition. You keep living the dream, I need to get back to work. Be well.

  24. This thread = :popcorn:

    I didn’t view Gary’s refusal to book the one-way flight to Iran for the girl as racist… not at all. The first two things that popped up in mind were: (1) Potential child trafficking, and/or (2) A girl who may be sent against her will (or blissfully ignorant) from a country with many freedoms/rights to one with very few rights for young females in the Islamic theocracy.

  25. Gary logs in as “Emma,” then criticizes himself just to get the comments and clicks going. Brilliant!!

  26. @GUWonder “A Caucasian of sort being racist against a Caucasian of a different sort is possible.”

    In response, I would like to quote the immortal words of Inigo Montoya:

    > “”Hello, my name is Inigo Montoya. You killed my father. Prepare to die.”

    Oh sorry wrong quote. This is the correct one:

    > “You keep using that word — I do not think it means what you think it means.”

  27. How the heck did this turn into a racist thread? Was that necessary? And, calling someone “boomer” (and he’s not) is rude. I found this post interesting; if you didn’t, scroll on by.

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