Frequent Miler’s 2023 Featured Image of the Year

I hope you’re not tired of our goofy antics, because we have another fun little contest to share: the 2023 Featured Image of the Year. Because of the way our blog posts are displayed on the homepage, each post gets a featured image assigned to it. This has become yet another outlet for having a little fun, which you know we are apt to do.

As the person who taught the team how to use the Photoshop-like web tool “Canva”, I take full responsibility for the goofiness you’re about to witness. But you have to admit, some of these creations are pretty clever. Here are my 10 favorite featured images of 2023, starting from number 10.

10: Mattress Running

This image appeared in Nick’s posts “An end-of-year mattress run decision” and “Should you mattress run the Bilt Hyatt Promotion?“

This image cracks me up because it emphasizes what a weird, niche term “mattress running” is. So niche is this term that our stock photography library can’t produce a better image for it than these guys literally running with a mattress.

(If you don’t already know, “mattress running” is not actually running with a mattress like these fellows are doing – it’s booking a hotel stay that you don’t necessarily intend on using, solely for the points, promotion, or status requirements it fulfills.)

9: Tim the AI generated teammate

This image was featured in Greg’s post “No joke – Tim goes full time” 

I loved this featured image from Greg’s April 1st post about Tim going full time because it generated some amusing comments from readers.

“Given the Photoshop skills of the FM Team, (and their fondness for practical jokes), how can we be sure that “Tim” isn’t a secret code for “Chat/GPT-generated content”? In any case, real (wetware) or virtual (software), welcome to the best blog on the web & keep up the great work!”

Now that you mention it…I’ve never seen Tim and ChatGPT in the same room together…

8. Trolling LifeMiles

This image appeared in Nick’s post “LifeMiles manual booking: patience compulsory, persistence pays off“

I love when the guys show a little bit of harmless snark. On its own, this image is pretty cute and funny, but it’s especially funny when paired with this caption from Nick in the post:

A live look at the LifeMiles manual booking team in action.

7. Fear and Loathing in New Zealand

This image appeared in multiple posts Greg wrote about New Zealand, including “Delta sale as low as 42K Skymiles roundtrip to New Zealand“, “Air New Zealand business class awards wide open close in” and “Greg’s New Zealand trip tips and recommendations“

I love the absolutely unhinged chaos going on in this picture, making New Zealand look like a Hunter S. Thompson piece. I’m not sure what sort of conversation the goat and the penguin are having there in the back, but it looks a little intense. And I don’t think that sea lion is going to share his wine any time soon, (to the utter disappointment of Gollum).

6. Hertz So Good

This image appeared in Greg’s post “Delta makes it Hertz so good“

This post was hilarious in and of itself with Greg basically turning it into a parody of John Mellencamp’s “Hurts So Good”, riffing off of the fact that Hertz had falsely accused a bunch of renters of stealing their cars. Apparently when Hertz does this, they also accuse the cars of aiding and abetting these crimes, which is why Tim and his rental car are both stuck in jail together. (As another layer to this funny little featured-image onion, Greg made this image shortly after Tim actually did have a Hertz rental car stolen in Columbus, Ohio.)

5. No Points For You

This image appeared in Stephen’s post “IHG Shareholder Rate: Save money, gain flexibility, but lose rewards“

Stephen really understands the art of making a good meme (and it was hard not just filling this whole post with them). I probably don’t need to even explain this reference to most of you, but just in case Nick is reading, this is taken from (the wildly popular and therefore probably dismissed by Nick tv-show) Seinfeld when George Costanza is denied soup because he had the audacity to point out that they’d forgotten his side of bread. “No soup for you!” or in this case, no cashback, points, or elite night credits for people using the IHG shareholder rate.

4. More Frequent Miler teammates in jail

This image appeared in Stephen’s post “I had to go to Mauritius because Australia thought my wife was a criminal“

Stephen was really lucky that Australia thought his wife was a criminal, otherwise he may not have had such a good opportunity to use this hilarious picture of him and his wife in jail. Was this picture taken at the Ohio State Reformatory? Alcatraz? 1880 town in South Dakota? Turns out Stephen and Shae have visited so many jails I’m beginning to see why Australia was suspicious.

3. Cat fight

This image appeared in Greg’s post “Stop telling me that value is what I would have been willing to pay“

If you find yourself in a debate that’s getting a little too spicy, I’ve found that picturing yourself as a disgruntled cat is a very effective way to lighten things up a bit. It’s hard to take yourself too seriously when you’re whiskered and adorable. (Is the gray cat Greg and the tan cat Nick maybe?)

2. Stephen strikes again

This image appeared in Stephen’s post “Wyndham shopping portal math strikes again“

This meme (and the commentary he added to it in his post) are a great demonstration of Stephen’s wittiness at work:

I particularly love this time of year because Wyndham takes us on a journey to somewhere that math rules no longer apply. I hope you have an itchy scalp because the Wyndham portal calculations will leave you scratching your head.

1. That time we all visited Santa and Tim became a thumb

This image appeared in Tim’s recent post “Frequent Miler’s travel rewards holiday wishlist“

So much to unpack in this crazy picture. First of all…how is Stephen’s dog Truffles positioned so perfectly on Nick’s lap? Did Stephen and Truffles secretly fly to Finland for this cameo? Secondly…why does it simultaneously look like Tim shrunk me to elf size but also made me look true-to-life? (And why did no one teach me that pointing is rude?)

Lastly…why is Tim depicted as a thumb with googley eyes? This is a fun little easter egg that I can actually explain! On April Fool’s Day, I replaced everyone’s images on the About Us page with goofy little smiling thumbs. Then, on April 2nd when I went to switch everyone’s pictures back…I couldn’t find Tim’s picture in the media library. So I messaged him that he’d need to send me another image of himself and until he did, he’d have to stay in his thumb form. I think it was several months before poor Tim got to go back to his human self. (When you’re AI, you can shape-shift like that.)

Tim wins! But did we miss anything?

If you want to join in on the fun, I’m all ears! Tell us about the Frequent Miler images (or quips) that made you laugh this year!

Want to learn more about miles and points? Subscribe to email updates or check out our podcast on your favorite podcast platform.