She Said Yes! 10 Tips to Pull Off the Perfect Airplane Proposal

It’s the kind of air-travel story that never fails to tug at the heart strings. Like an excited child on her first flight. Or someone getting a free first-class upgrade.

Two more fliers joined the mile-high club — of marriage proposals. Last week, pilot Eric Greener, a pilot on Ravn Alaska, proposed to his girlfriend, Alaska Airlines flight attendant Brandy Hollenbeck.

Hollenbeck had no idea her boyfriend, whom she hadn’t seen in 19 days thanks to their busy airline schedules, was on the Seattle to Juneau flight she’d been working; the flight crew had sneaked him aboard and placed him in the cockpit’s jump seat. It was only when Hollenbeck had started beverage service when Greener popped out of the cockpit, took over the plane’s intercom and popped the question.

“Brandy Hollenbeck, I’ve loved you since the moment I met you and I want to be the man for you for the rest of your life,” Greener says in the video, which was shot by an Alaska Airlines employee. “Will you marry me?” Cue applause from thrilled passengers, tears from a shocked Hollenbeck (she was so taken aback she’d forgotten to say yes), and a loving embrace between the newly engaged couple.

But proposing to your beloved isn’t just a simple spur-of-the moment thing. It takes the secrecy of a CIA spy, the organizational skills of an air traffic controller and the stealth of a ninja.

Yahoo Travel approached Arvin Shandiz, who had his own mid-air marriage proposal go viral back in 2011 (he and now-wife when Alexandra Williams have been married since 2012), for tips on how to pull off a romantic, high-flying feat.

Arvin Shandiz, whose mid-air proposal to his girlfriend went viral in 2011, shares advice on planning the perfect mid-air proposal (Video: Arvin Shandiz)

1.) Make it meaningful

You can propose on an airplane just for the sake of proposing on an airplane, but it will have more resonance if there’s a symbolic reason. Greener and Hollenbeck already had Alaska Airlines to thank for their relationship: they got together after Greener’s mom, who’d taken an Alaska Airlines flight on which Hollenbeck was a flight attendant, fixed the two of them up.

Related: Rules of Flying: Ex-Flight Attendant’s Top 10 Airline Etiquette Tips

Shandiz tells Yahoo Travel that he, too, had a connection with the flight on which he proposed: Delta’s New York-Chicago shuttle was the flight on which he first met his now-wife, who’d struck up a conversation with him after watching him help an elderly passenger with her bags. “It’s funny because shortly after we’d started dating I told her ’I’m gonna propose to you on that same flight where we met.’” Shandiz tells Yahoo Travel. ”And she just laughed it off and thought I was crazy.”

But that’s exactly what he did. Both proposals provided a nice, full-circle moment to their relationships.

2.) Get help from the airline

Flying the friendly (and romantic) skies. (Photo: Thinkstock)

One thing Shandiz has in common with the latest guy to pull off a mile-high marriage proposal: they both had help. Sheerer had let the Alaska Air flight attendants and pilots know beforehand what he was planning and enlisted their help sneaking him on board and orchestrating the proposal.

Shandiz highly recommends letting the airline in on your plans. “I’m of Middle Eastern descent, so I’m not gonna just get up in the front of the plane and try to get on the PA and propose,” he laughs. “I wasn’t going to do it if I didn’t get help from the airline.”

Shandiz reached out to Delta’s PR department, sending them an email about how he’d met his girlfriend on one of their flights and asking their help in planning it. “They were all over it,” Shandiz says. “They helped me organize it and we came up with a plan of how to do it.”

Delta smoothed things over with airport security and the crew of the flight in question. Shandiz says a Delta PR rep was even on board the flight; she was the one who got the whole thing on video.

3.) Plan EVERYTHING

While you can book an airline ticket last-minute, planning a last-minute airline proposal is a no-no. Both Shandiz and Greener’s proposals plans were months in the planning; it takes a lot of doing to get an airline and flight crew in on a proposal. “Make sure it’s very well planned out,” says Shandiz. “You don’t want to hit any snags or have anything unexpected happen. The planning really goes a long way.”

4.) Make sure your intended is okay with public proposals

Being proposed to on a plane full of people can be stressful enough; and if you get your airborne proposal on video, it could very well end up going viral and being played on morning shows. So you have to make sure your beloved is okay with such an intimate moment potentially becoming national news.

That was a big question mark for Shandiz’s mid-air proposal. ”My wife is a private person,” he says, adding that she likely would not have opted for a public proposal had she had a choice in the matter. But he says after seeing the lengths to which he’d gone for his super romantic proposal, his wife was okay with it. Besides, he says: “I figured hey, I told her along time ago that I was going to do this, so I was being honest.” It helps to be a man of your word. But on the other hand…

5.) Make peace with lying

That whole “honesty-in-relationships” thing? It’s not gonna work if you’re planning a top-secret mile-high marriage proposal. This is probably going to be the last time it’s okay to lie to your beloved, so be sure you do it well. For Greener that meant giving Hollenbeck the impression he wasn’t interested in any talk of marriage. Hollenbeck tells Alaska Dispatch News that Greener was so reticent about any marriage discussion, she’d started to worry that they’d need to “have a talk” about it.

Related: The Top 5 Most Decadent ‘Bachelorette’ Proposal Locations

Shandiz openly lied to Alexandra on the day of his proposal. As part of the proposal planning, the airline had upgraded the couple to first class, a fact that set off alarm bells within his sharp-eyed companion. “Alex said, ‘I think this is wrong. We should tell them.’” The only way Shandiz could mollify his suspicious fiancee-to-be was to tell her that his frequent-flying father had booked their tickets and had scored them an upgrade.

Hey, there’s no room for truth in top-secret marriage proposals.

Why not propose on a plane? (Photo: Thinkstock)

6.) Make sure your spouse doesn’t sweat the small stuff

You can plan your proposal down to the last detail, only to have it unravel when a rude gate agent, a long security line, or a delayed flight puts your beloved in a foul mood that’s not compatible with the biggest day of her life. So make sure your intended isn’t the type to get too rattled by the routine indignities of air travel.

“She’s generally very happy-go-lucky,” Shandiz says of Alex, so he knew she’d be in the right frame of mind for his marriage proposal. Besides, because he’d enlisted the help of airline staffers in planning the whole thing, they made sure none of those typical frustrating airport mishaps happen. “I think because everyone had been briefed about what was going down, there was a very small chance that something unpleasant was gonna happen."

7.) Have a plan for the security line

This may not have been an issue for airline pilot Greener, but for the typical commercial air travelers, the security line presents perhaps the biggest danger to a top-secret airline proposal. If a sharp-eyed TSA agent plucks your engagement ring out of your carry-on right in front of your beloved, the jig is up; your airplane proposal now becomes a security line proposal.

"Like I said, I’m of Middle Eastern descent and I almost always get randomly checked in security,” Shandiz says. “So before we went through security, I went to the bathroom, took the ring out of my bag and slipped it into my pocket.” He figured there wasn’t enough platinum in the ring to set off the metal detector. And even if it had, Shandiz had a plan for that, too: had the TSA agents pulled him aside for additional screening, he says he planned to secretly show them the ring and ask them to keep it on the DL.

Shandiz had another smart idea about the security line. “I had Alex go through security before me,” he says. That way, if there were any drama surrounding the ring, he knew she’d be too distracted getting her shoes and bag to notice.

8.) Don’t get nervous

One thing you can tell from the videos of Shandiz and Greener’s proposals: both men displayed no fear and no shame with their bold (and public) pronouncements of love for their girlfriends.

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“I wasn’t nervous at all,” Shandiz says. “I didn’t let myself get nervous. I was like, "This is it: I’m doing it!” This is game time, fellas: seize the moment!

9.) Make sure she’s going to say “yes”

Destination: romance. (Photo: Thinkstock)

"My first advice would be to be damned sure they’re gonna say yes,” says Shandiz. That’s a good rule for any public marriage proposal, be it on an airplane or Jumbotron during a big game. Shandiz says once the video of his proposal went viral, commenters pointed out just how risky his plan was. “People were like, ‘Well it’s a good thing she said yes, otherwise they’d be stuck next to each other for the entire flight,” he says. “Obviously I wasn’t gonna do something like that if I didn’t think she was going to say yes.”

10.) Don’t expect flying to get more pleasant after a mid-air proposal

One would think that making such a lasting memory aboard an aircraft would forever make flying a joyous experience that calls to mind one of the greatest moments of your life, right? Well Shandiz says now he and his wife rarely think about it. “It doesn’t really come up because we travel so much and we fly a lot,” he says, noting they usually forget about it until someone who’s Googles them brings it up.

Still, Shandiz wouldn’t have done it any other way. “I think at first it as overwhelming to get all the attention,” he says. “But at the same time it was a good story. Everyone’s looking for a good story.” And in an era in which flying isn’t always the best experience, nothing beats watching a flight turn into one of the best moments of a couple’s lives.

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