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The Challenges and Rewards of Booking Miles and Points as a Couple

a man and woman standing in front of a waterfall

Sharon and I have been traveling with miles and points for probably close to twenty years. Over the years, Sharon has had to learn that I’ll randomly bring up some plans for a trip or credit card (Note from Sharon: #rolleyes). Meanwhile, I’ve learned that she doesn’t care about the details but, given limited guidelines, will do her part to help us earn extra points and miles. Nothing about either of these has changed.

Through experience, I’ve learned that traveling as a couple brings a certain number of challenges to booking award tickets. However, playing this game as a couple also has several advantages. I love the analogy that Sharon and I are now playing with points and miles in Two-Player mode. For those who are familiar with video games, this brings a whole number of advantages but also presents a set of new challenges.

I wouldn’t trade anything for the experiences we’ve had on our travels, but I feel it’s necessary for anyone who’s going to try to take on this responsibility to understand the thankless number of hours they’ll spend making trips work for the two of you.

CON

I often read articles about people booking an award seat on Lufthansa or Singapore in first class at the last minute. It’s possible to find that space if you’re looking for just one person. When you need to find two tickets, good luck. I’ve put many of those “dream” tickets out of my mind, and I focus on things that are possible.

PRO

It’s always possible to find those once-in-a-lifetime tickets for two; it’s happened to me… TWICE, but I’m not holding my breath. I was told that finding two first-class tickets to Japan on ANA would happen when H*LL froze over, but here are pictures of us in our first true lie-flat seats, back in 2009.

OMG. That MacBook was HUGE!!!!

So it pays to shoot for the moon – even if you miss, you’ll be among the stars and able to get way more than you would have otherwise.

CON

However many thousands of miles that flight cost in 2009 (I want to say 120,000 miles plus $582 in taxes?), It costs double that for the two of us. It was an experience I’ll never forget. Well, I forgot a little because I had them open a bottle of Shōchūand they insisted on refilling my glass for the whole flight.

PRO

If you need to spend twice as many miles for trips, you can rack up miles twice as fast with credit card sign-up bonuses. Since we both have our own businesses, we can double-dip on all the good personal and business card offers.

CON

Keeping track of all of those credit card accounts takes time. I’ve been known to miss a payment or two (only by a day or two but it still triggers a late fee). Since Sharon will only call a bank if she has to, I need to make sure it’s worth it to plead about waiving the fee. It has to be worth what we’re going to get out of the call and I also need to decide if it’s worth it for our marriage. (Note from Sharon: True story! Happy wife, happy life! LOLOL!)

PRO

Your traveling partner occasionally appreciates it when you can pull off that travel unicorn. She might have been able to get us tickets to see Harry Potter in London a few months after it opened (back when it was a really hot ticket), but I was able to get a room for the trip using award nights. While booking flights costs twice as much, hotels are the same price if you’re looking for one or two people. You can also leverage hotel points from both people to stay in fantastic places, like a suite at the Renaissance St. Pancras.

CON

When your travel partner wants to visit New York over Thanksgiving weekend, she expects that you’ll be able to find flights and hotels using points. If you were wondering, I did, using a combination of British Airways Avios, Delta SkyMiles and Marriott Bonvoy points. Here’s how I did it. 

PRO

We can leverage a combination of cards and programs by having two people playing. It’s not that bad. In fact, we might have too many free nights per year from our credit cards.  In addition, I have the Sapphire Reserve from Chase to earn 3x points on all travel expenses and to get the 1.5 cents per point value on redemptions through Chase Travel. I’m also an authorized user on her Sapphire Preferred card, allowing us to transfer points between Ultimate Rewards Accounts quickly.

CON

I’ve been doing this for years, and our account sign-ups and links are layered on top of one another. If I were starting over, I’d do it differently, but it’s too late to go back now.

That’s a glimpse of the trials and tribulations of booking miles and points as a couple. From the one doing most of the planning, it’s been worth it.  Like the first international award we booked to visit Japan:

I just hope Sharon remembers that the next time I ask her to call a bank to get a retention offer on a credit card (Note from Sharon: UUUUGGGGHHHH!!!!).

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