I’m My Own Worst Enemy When It Comes To Booking Family Travel

Filed Under: Travel

There aren’t many things in life I’m good at other than singing along to Taylor Swift songs in the shower, getting irrationally excited every time I see a goldendoodle, consuming lots of champagne without getting hungover, oh, and being able to predict award space.

And sometimes I feel like that’s a curse. Or I just need to lower my standards.

Case in point — if there’s one thing I love more than flying a great airline product, it’s making sure that my parents are flying as comfortably as possible. Nothing makes me happier than when they’re happy.

My mom wanted to go to Germany for her birthday this year, so she phoned me up to see what could be done with miles, about a month before she intended to travel.

“Okay, what day do you need to leave?”
“June X.”
“We’ll make that work. There’s nothing good right now, but I promise something will open up. Lufthansa opens first class space at most 15 days out, while Singapore often has space close to departure as well.”

Understandably she was a bit apprehensive about not actually having a ticket booked to Germany. I get that. But at the same time, I’m an expert and she should trust me… or so I’d like to think.

“I really want to plan, is there nothing at all available?”
“Well yes, there’s Lufthansa business class available, which you hated.”
“Oh that’s fine, I just want to know exactly when I’ll arrive so I can start planning.”
“But it’s Lufthansa’s old business class. Remember, the product you thought was so bad that you assumed your seat was broken when you put it into bed mode?”
“I just want to get to Germany, that’s fine.”
“No. I’m not letting you fly Lufthansa old business class for your birthday. That would mean I’ve failed you as a son.”
“Oh please just book Lufthansa business class.”
“Please just trust me. Please. I promise I’ll get you there in the morning on June X in a better product.”


Understandably, after that conversation she started texting me about eight times a day to see if anything had opened up. Which I totally get. Because for someone who doesn’t spend all day looking at award space, it seems kind of inconceivable to think that I could “guarantee” something better when it wasn’t in fact open.

Fortunately space did eventually open, in Singapore Airlines Suites Class to boot.


Between that flight being wide open and another “flagship” Lufthansa flight not having a single seat occupied in first class, I knew it was a sure bet.


Of course now my mom is incredibly excited about flying Singapore Suites Class (and my dad had faith in me all along, so he wasn’t worried one bit about space opening — though I don’t think I’ve ever failed him when it comes to travel planning), but my goodness was it a battle!

As usual I checked award space constantly, but dealing with the constant questioning and intermediate sadness made this one of the tougher awards I’ve had to book, despite how straightforward it was.

I guess what I should have done is book Lufthansa business class as a back-up, and then later switched when something better opened up. But I really didn’t feel like calling Avianca LifeMiles to cancel an award and I knew space would open, so…

Or I could have just booked Lufthansa business class and kept that as the award, and I’m sure she would have been happy about it. But I was holding her travel to a higher standard than she was.

On the plus side, I’m sure she won’t mind too much when she’s on her Singapore flight and asked whether she wants Dom or Krug. 😉


Has anyone been in a similar situation with family, where you hold your family’s travel to a higher standard than they do, much to their frustration?

  1. Nailed it. I cringed as I read this one. Yuck.

    Obviously what you should have done is lied, told her it was booked, even when it wasn’t. Then later you’d book it and she’d never been the wiser. Which you would never do. Except that one time as a teenager, when…

  2. it’s not just family… it’s any time i help someone who doesn’t understand how these things work. i am now helping a friend booking trip to South Africa and i advised him to transfer Amex membership points to Delta to book a trip on Virgin via London (there is availability on his very exact date, short connection etc).
    he simply doesn’t get it… he thinks it’s impossible to use Delta skypesos to book Virgin… he just won’t do the transfer. uh…

  3. What a great son! Sounds like Mom will have the time of her life on SQ. (Ummm…I would have been texting you 8 times a day too.)

    Advise Mom, no talking to strangers this trip. 😉

  4. I’m also trying to book my mother a flight from LHR to MNL in late July using LifeMiles. Cabin doesn’t matter, but there’s no availability across all three classes. Do you think I should hang on for an opening, or should I bite the bullet and buy a ticket?

  5. Having same issue booking family on trip to Hawaii. Last year when traveling with my wife I change departure out of Hong Kong 3 times till I got CX F HKG to JFK.

  6. My … cousin.
    I just introduced him to this game a few months ago and he learned it fast.
    He’s planning a trip for his mother and brother to Asia next year, on CX J thanks to Barclays US Airways and Citi AA cards. He applied both for his mom and bro and they all got approved.
    Everything worked out flawlessly, points were posted, flights were booked.
    One day, his mom said:”Son, cancel the ticket. We should not fly like this. It looks like it’s illegal to me. I’m scared someone will arrest me. There is nothing free in America. There is no way we can fly roundtrip in business class to Asia for 200 dollars”.

    OH LOL.

  7. I know the feeling. Star Alliance had tickets to Spain for $1800 in business class. As I’m carefully deciding which Lufthansa plane to put my mom on, the sale goes poof…

  8. “No. I’m not letting you fly Lufthansa old business class for your birthday. That would mean I’ve failed you as a son.”

    That is some serious self-imposed pressure.

  9. Lucky – Are you using the Lifemiles website to monitor for flight availability or just to book SQ? LH? Or?

  10. What is the best way to check SQ availability… the only time I’ve seen it was when I lucked out on a FRA-JFK on the Aeroplan website.

  11. @ Harvey Yang — Since Singapore makes most space available exclusively to members of their own program, you’ll have to check directly through their website.

  12. @ Stephan — I’m using Singapore’s website to search Singapore availability, and Aeroplan/ANA to search Lufthansa’s space.

  13. @ Anton — If she has a bit of date flexibility I’d say there’s great odds of space opening. I may hold off a bit.

  14. @ Lucky’s Reader — I mean sadness over not being sure if the trip will work out, etc.

  15. I feel like I’M the mom! I’m the one with the anxiety when what I want isn’t open…RIGHT NOW. lol.

  16. I have. Was ticketed on Avios in JAL on their NRT-JFK 787 flight in biz, but I really wanted to fly their 777-300 in new First. But nothing was opening up, yet I knew there were still 6 empty seats in the cabin. Sure enough 3 days before my flight home, a First class seat opened up. I ticketed myself and immediately thereafter cancelled my Biz class ticket on the 787. What’s so wonderful about BA’s exec club is you can cancel until bat 24 hours before and get full refund and miles posted back to your account pretty much instantly.

  17. Funny post. Maybe book her now for next year and then you will be all set….well in biz class for now then you can change it to first last minute if anything opens up closer, right? Hopefully you are taking the JGK – FRA route and not the long way through SIN? Haha. Unless she likes that way.

  18. any advice on best way to get to Barcelona in July 2016 for a cruise? would like to then fly to Greece for 4-5 days before heading back to Washington DC or BWI. Greece can come before the cruise too. We have 600,000 AA pts, and 350,000 ultimate rewards pts, 50,000 alaska and 60,000 virgin elevate pts, 50,000 TY pts, & 50,000 starwood pts, Will be getting 150,000 membership rewards pts soon too. Would love to fly business, would be 2 adults and 2 kids. best options to look for?


  19. Hey Lucky, I impulsively decided to book a quick trip to DAY-HNL leaving next Tuesday (9th) as a birthday surprise for hubby. Wanted to fly AA business/first saver…nothing really open right now that fits our schedule. Any chance of you knowing if AA opens domestic flights to HNL a day or two beforehand? Any info would be helpful! Thx!

  20. Me and my Dad flew Singapore F from John “Eph” Kennedy:) to FRA. He acted as if maybe we should wait for the ticket (secretly hoping the space would disappear). We got the SIA ticket and he was over-the-top stoked when we got on the plane. After pre-departure beverages he says:”I vas hoping zis plane would fill up and we would be forced to fly Lufthansa.” (My dad and I both love lufthansa, but LH business over SIA F) He then said “I’m glad ve booked zis instead, just to give it a try, now I know what I vhant next year, Lufthansa.”

    I’m seriously worried about my dad, he said he would rather fly angled LH business then SIA F.

    In the end all was good, he got his LH fix on our connection from FRA-HAM and on the way home FRA-DEN with new F. We also enjoyed the brand-new 737-900 that United flew us on from DEN-JFK. It had these new, blue seats in F and blue leather slimline back in coach.

  21. This is a very timely post as I am feuding with my mother over her upcoming trip to her hometown of St. Petersburg, Russia. In previous years she would fly economy on Delta from SFO to SVO via JFK and then take an Aeroflot flight up to LED.

    This past weekend I decided to surprise her. Thanks to Lucky, I knew Transaero had some great fares for Imperial Class. So I got her on UN’s flight from LAX to Vnukovo–in Imperial Class!–and then connecting to LED. It was an unbelievably great deal. Pretty cool, huh?

    Not according to my mother.

    “Who asked you to spend so much money! Have I ever complained about sitting in economy? Did I not teach you the value of frugality? So I guess I now have to buy a new dress just so I don’t look like a peasant in your fancy Imperial Class…”

    And on and on it went…until she stopped talking to me altogether.

  22. If you booked with Life Miles and had to cancel, you can always have Tiffany cancel it for you since her baseboards are looking a little rough. Or book your parents in the old LH business class and then sue LH…lol

  23. Family is my constant struggle. I’m always happy to help my parents book flights with their points, but they never seem satisfied.

    2 biz class aa seats on the 777-300ER in biz from LAX-LHR over peak summer months on the exact days she requested? Mom complained the connections were a little long.

    2 first class qantas seats DFW-SYD one week before Christmas? Parents didn’t like the idea of booking with BA and then canceling.

    2 ritz Carlton cards and a little patience to earn a Southwest companion pass for 24 months? They were worried it wouldn’t work. (I was a little worried, but don’t tell them, because it totally worked!)

    I keep on telling her she’s going to enjoy it. And she does. But man! It’s a struggle. My dad just smiles and goes along with the ride. Family. Love them.

  24. It is often a great plan to not burden people with more information than is needed. 100% of the time, I share with my family and business associates that “it is handled”. Often, as with FOX News, we can even make up our own facts….

  25. Father when I told him that I’d be flying to Hong Kong for the first time on Cathay in first class via Aadvantage points: “Don’t come complaining to me when something goes wrong and you have to fork over money to BUY the ticket for the seat on the plane!”

  26. I had a meltdown this week for similar reasons. Perfect flight first class on Swiss to Milan and return air Canada business. Amazing price. Went to book that afternoon and poof, price tripled. My partner didn’t understand why BA business was a let down. I was shooting for platinum status on united and we would fly Swiss first! Don’t you understand!

  27. @ Missy — They sometimes do, but it’s not all that common, given how many people are trying to upgrade. I certainly wouldn’t count on it, unfortunately.

  28. @ TJ — With American miles it shouldn’t be too tough, though you’re not going to be able to do a stopover for free. I’d look at space on airberlin or Iberia, to avoid the pesky British Airways fuel surcharges.

  29. Wow, talk about self-absorbed. Instead of simply listening to what your mother actually wanted, you caused her needless stress and worry by imposing your desires on her. This time it worked out in the end, fortunately for you. But next time? Sure she seems happy with what she ended up with, but it was obvious from the beginning what she really cared about was being in Germany for her birthday and having that locked in ahead of time. Believe it or not, many people just care about getting to their destination and not all the fluff and BS with getting there!

  30. Lucky, i havent seen you fly SQ in a while so how where you able to have enough Krisflyer miles for the redemption? did you transfer the miles from another program?

Leave a Reply

If you'd like to participate in the discussion, please adhere to our commenting guidelines. Your email address will not be published. Required fields are marked *