How do you surprise someone who wants to be surprised?   That’s the problem I faced proposing to my girlfriend.  If I did anything out of the ordinary, she’d be suspicious.

I knew I wanted to do it around New Year’s — which would give us enough time to have a summer wedding — but as that day grew closer, I still found myself without any good ideas.  Should I use some of my old childhood magic skills to make the ring “appear” somewhere unexpected?  Should I use some tricks I learned in film school to do it with a heartfelt video?  At the time, I was just getting into the tech consulting biz.  Should I do something high tech?

Three days before my target date (Saturday, Jan. 1st), we went out for sushi.   My eyes kept wandering onto a TV in a corner of the restaurant.  And it hit me.  I pictured us sitting down to watch a Netflix movie at home.  Mid-way through the flick, a character would get down on one knee to propose to another, and that’s when I’d get up, walk to the TV, reach into the film, and pull the ring out of the movie world and into ours.  And then I’d propose with THE RING THAT WAS JUST IN THE MOVIE.   No way she’d see that coming.

I had no idea how I’d do it exactly, but I knew it’d require a little bit of magic, a little bit of filmmaking, and a little bit of techie know-how.  As soon as I got home, I started working on the following plan:

On Saturday, when I’m at her place, we’d get a disc in the mail from Netflix.  But what disc?  It’d have to be both a movie that’d realistically be on our Netflix cue, but also something with a half-decent proposal scene.  I rented a bunch of DVDs, scanned through a bunch of movies, and settled on…

Leap Year, starring Amy Adams.  It was a romantic comedy that came out within the last year that neither of us saw in theaters, so it could realistically be on our Netflix cue.  It had a proposal-like scene in the 1st ten minutes.  Perfect.  I’m not going to wait two hours to do this thing.  Also, Melissa always falls asleep twenty minutes into every movie we sit down to watch together.  I mean always.  I had to beat the clock.

I’d rip open the envelope, pop the disc into the DVD player, and we’d sit back to watch the movie.  Ten minutes later, Amy Adams and Adam Scott would be on the TV, dining at a super-fancy restaurant, where Amy thinks Adam is going to propose to her (Spoiler Alert:  He’s not, but Melissa doesn’t know that).  So basically, their situation is the exact opposite of ours in every way.

Adam reaches into his pocket, pulls out a small jewelry box, and places it on the table.

Amy looks down at the box and lights up.  This is the moment her character has been waiting for her entire life.

And it’s at that exact moment the DVD will start to get glitchy…

After a moment of skipping, the DVD will freeze on the image of a jewelry box on a restaurant table.

Melissa will think the DVD is scratched.  I’d say “let me take a look at it.”

Then, as I reached behind the TV to “fix” it, Melissa will see…

…my hand and arm, reaching into the movie, grabbing the jewelry box, and pulling it out into the real world.

“I found the problem,” I’d tell her.  “This isn’t for Amy Adams.  It’s for you.”

At least that was the plan.  And for the most part, that’s how it went down.  Read on to find out how I did it, what went right, and what went wrong…

Continue reading “How does a techie/filmmaker/magician pop the big question?” →