How I Pulled Off A Surprise Trip… Sort Of

Filed Under: Travel

Now, this is more of a personal story than an airline or hotel review, so if that doesn’t interest you, feel free to skip this post. I figured I’d share the story of how I pulled off this surprise engagement trip, even though I usually suck at surprises.

Ford and I talked about the possibility of getting engaged a while back, and at the time I jokingly said “let me surprise you.” If I recall correctly he laughed out loud, because I’m the worst person imaginable at surprises. Hopefully there are a few reasons Ford loves me, but my ability to surprise isn’t one of them. I’m just absolutely horrible with surprises, partly because I’m not at all creative, and partly because I have a terrible poker face.

The last big surprise I pulled off was with my dad, when I took him on a round the world trip for his birthday. But that was easy enough to do, because my dad quite doesn’t have a cell phone and doesn’t use the internet, so that was a secret that was super easy to keep. Furthermore, he knew we were going on a trip, just not where we were going. This was different.

While I’m not quite sure how I got myself into this, apparently I was proposing, and apparently it was going to be a surprise, because I can’t turn down a challenge. Oops. However, I didn’t give a timeline, and did say we had so much going on, maybe later this year, etc.

However, in this case we were in NYC for a weekend for some family commitments, and I figured this was the perfect opportunity to pull off a surprise trip.

I met Ford in NYC, and I told him before that we’d be flying back to LAX on American on Monday at 3PM. I explained that American was opening their Flagship First Dining facility that week, and I wanted to be among the first to review it. So I told him I booked us $650 business class tickets on American and managed to upgrade them to first class with Business Extra certificates.

I figured this story was believable since:

  • Ford knows how focused I am on reviewing things as quickly as possible
  • I got a deal on the flight, as far as he knew, and Ford knows I can’t turn down a deal

In reality I had just booked fully refundable American first class tickets to LAX. Little did he know that I had Air Serbia tickets booked from New York to Belgrade, departing around the same time.

Sometimes I’m not great with details (to put it mildly), and this was one of those cases. I had the flights and hotels figured out, but I hadn’t actually decided when I was going to tell him we weren’t going to LAX.

I told him I wanted to go to the airport plenty early to review the new lounge, so we took an Uber to JFK at around 9AM, and asked for us to be dropped off at Terminal 8 (American’s terminal).

We had our mobile boarding passes for our flights to LAX, and as it turned out, we were able to get a tour of the new Flagship First Dining facility. This was totally coincidental and had nothing to do with my grand plan. That’s because the Flagship First Dining facility open was delayed, so we couldn’t use it anyway.

We got a tour of the lounge, and probably spent about an hour in the Flagship Lounge. We had stored our luggage in the lounge, and I said “let’s get our luggage.”

We  got our bags, and at this point I walked towards the elevators and pushed the “down” button.

Ford asked “where are we going?”

Like I said above, I hadn’t actually thought through how I was going to execute this, so I was kind of just going with it.

“I’m hungry, let’s go eat something.”

“But they have food here?”

“Meh, it doesn’t look very good, let’s go to that Michael Jordan’s Steakhouse thing.”

Ah, crap, because the food actually did look pretty good, and I think Michael Jordan’s Steakhouse is at Grand Central Terminal, and not JFK Terminal 8. Oops. 😉

“Michael Jordan’s Steakhouse? What are you talking about?”

“Actually… we’re not going to Los Angeles.”

“What do you mean?”

“We’re not going to Los Angeles!”

“But… I thought you booked non-refundable American tickets and upgraded us?”

“Nah, those were just refundable tickets.”

Ford had a confused look on his face for about 10 seconds, and then a big smile on his face when he realized what was going on. And if I’m being honest, I almost cried a bit, and I’m not someone who ever shows emotion.

I wasn’t thinking straight at this point. While I can usually walk through a terminal with my eyes closed, I think I took about 40 wrong turns while getting us from Terminal 8 to Terminal 4.

At this point I still hadn’t actually told Ford where we were going. He eventually found out we were flying to Belgrade when we got to the Air Serbia check-in counter, though I still didn’t tell him where we were going from there. So all he knew at this point was that we were flying to Belgrade.

Two hours later he was happily ensconced in his Air Serbia business class seat, still trying to figure out where we were going.

I have to be honest, I was a bit worried that Ford would see this coming. One concern was regarding his passport, which I didn’t think he’d bring. So I had someone back in LA ready to overnight it to NYC if needed. When he got to NYC I checked his bag, and sure enough he had packed his passport.

I asked him about this after the fact, and he said that I’m crazy and he never quite never knows where he’s going, so he always packs it. He has learned well, eh? 😉

I was relieved when I found out that he was actually caught off guard… whew.

  1. Reading the early installments, I was taken back a bit about how much was spent on the trip. Seeing Ford’s smile in the picture above immediately confirmed that who care how much it cost, our experiences we share with loved ones ultimately what we all should strive for. Sure, money can provide an avenue for such experiences, but happiness we create is worth way more than the monetary outlay.

    Can’t wait to read the rest of this TR.

    Cheers, friend!

  2. Congrats Lucky! I can never surprise my boyfriend either (he always finds out somehow). I can’t wait to read about the rest of the surprise!

  3. Interesting story … but I think that buying “fake” tickets pulling inventory off the system for the LAX flight to intentionally not get it is wrong, just wrong.

  4. Congrats Ben & Ford!
    Your names make it really easy to come up with a couple name – henceforth you will now be known as: Benford.
    Seriously, this is awesome and couldn’t be happier for you both!

  5. This is THE CUTEST! I hope you remembered to cancel the AA tickets haha.

    Can’t wait to hear about the rest!

  6. @b_trav — Eh, there’s a time and place for everything. It’s not like it’s a regular habit. Something tells me the giant corporation will be just fine and didn’t get its feelings too hurt.

    And it’s not like those seats would ever be available with miles, given AA’s recent shenanigans…

  7. @Bill — Your comment is disrespectful and inappropriate. I’m not sure whether you intended it that way or were trying to be funny, but it’s a bizarre to read such a remark on a celebratory post. Obviously the idea that there is a “man” and a “woman” in a gay relationship is a dated and ignorant trope. Perhaps you could clarify by wishing the newly engaged couple well if you didn’t mean to give offense.

  8. Cute story. Thanks for sharing. I’m 1 for 2 in surprising my wife with trips (one of these days, I’ll share the story on my blog of how I was 24 hours away from pulling off the 2nd), though neither was nearly as involved as this one. Kudos for pulling it off!

  9. Congrats on this exciting development. Onward with progress. Now you just need to fire Daniel then this will be a proper blog again.

  10. I literally got nervous for you as I was reading this story. Heart racing and everything. Can’t wait to hear how the rest of the trip went. Congrats to both of you!!!

  11. Very sweet. Seems like if you had your surprise planned it would be less like you, so it was perfect. Congrats!

  12. @rf Will people stop hating on Daniel?! He provides reviews of products Lucky would not usually review. He brings a different background and personality to the blog, and it’s good to have other people posting than just Lucky and Travis.

    If you don’t like him, don’t read his articles, on the front page of OMAAT the author of each article is clearly stated!

  13. All the best guys! Reading this really made me smile. Looking forward to hearing about the rest of the trip.

  14. The smile on your loved one’s face gives a definite answer to your proposal. This romantic saga surpasses the tender moment Ertugrul proposed to Halime in the Turkish soap opera Dirilis: Ertugrul. 😉

  15. Congratulations! I love planning decadent, luxurious trips for loved ones as well, and I”m so glad this worked out! And it seems like you’ve found the perfect guy: one who always packs his passport and goes with the flow when you tell him you’re going to Belgrade after you’ve gotten to the airport. Can’t wait for the rest of the story!

  16. why are most of these luxury travel bloggers always gay? what is it that attracts gays to luxury? is it because they get made fun of their whole lives and then need something to prove to society?

    plus did you hear how queer sounding that ford kid sounds speaking? so annoying. ben at least sounds like a man speaking. man up a little dude!

  17. So jelous of you guys, unfortunately the quality of gays in Australia is meh. Maybe I’ll have to love to the us

  18. Beautiful and romantic. Congrats to you both.

    @Bob poor fella . You need to cum out the closet me thinks

    @rf you seem to be jealous of Daniel. Lol. Pathetic creature

  19. Hey @Bob – how about your man up a little and stop bullying people you don’t know Sh*t about. Also, why do people call themselves Bob. They must have a better name to use? Same analogy. Stupid questions – Stupid answers. Please don’t be disrespectful towards anyone you don’t know in the future. It would be a shame for Karma to bite your in your A**. Thanks!

  20. A wonderful story. I always want to surprise my husband with a trip but he’s not a US or EU citizen and needs a visa for most countries.

  21. Congrats, gents! Wish you both so much happiness and fun adventures in your life together! I’ve loved your trip reports for years, but I am especially excited to read each installment of this one. Congratulations on the engagement, and an almost bigger congratulations for putting in so much thought to make it special and managing to pull it off!
    And to the idiot with the “man in the relationship” comment- what’s wrong with you? Don’t try to tarnish someone else’s happiness with your ignorance. And asking who’s the “man” or “woman” in a same sex relationship is like asking which chopstick is the fork.

  22. Congrats ben! Amazing story and I hope the best for you and Ford!
    I would just like to know what you do with your kids when you travel? My husband and I always have trouble with this! Would you mind suggesting things for me?

    Thanks so much and congrats again!

  23. So cute. 🙂 Your nervousness and bewilderment after you sprung the surprise trip on Ford is so adorable. Can wait to read the rest of the story!

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