A Decent (Wedding) Proposal

Here’s another story I wrote for my friend Rachel Rosenthal’s fabulous blog Bridesmaiding (which you can visit here).

I’ve never actually successfully beaten my brother at a game of Monopoly. I’ve never attempted (nor even considered) a government coupe. And I’ve certainly never attempted a heist. I’m telling you all of this because I think that I am like most men in that I have neither the skills nor the intellect to devise a strategic plan that seems impossible, but through careful planning, is ultimately triumphant.

Most men of my generation — raised on Rube Goldberg devices, Tom & Jerry and numerous episodes of MacGuyver and The A-Team – really, really, really want to get the money, the girl and thwart the bad guy just like George Clooney in Ocean’s Eleven. But in reality most of us are just trying to get by on the limited skills and talent that we’ve amassed over time. In short: we aspire to be Danny Ocean, but in reality we are all just Billy Ocean (Google it, Millenials). Which is why most marriage proposals are a goddamn mess.

The brilliance of a wedding proposal is that the odds are greatly in your favor–you know (mostly) that the woman you’re proposing to wants to be married. But we also know that the “Yes!” is only half the battle. She will also want a story to tell her friends and family, and that is the loot in the vault that every man tries so desperately to nab.  Sure the woman will not really care about the lengths with which her man will go to in order to pop the question. I knew of a woman that was lured to her rose-and-candle-filled apartment for her proposal by her boyfriend’s request that he needed to get home immediately so that he could take a shit (I’m paraphrasing of course).  She still said yes.

But we want to do better. The gentleman I just mentioned only used his faux-defecation (or de-faux-cation if you will) when his initial plan with lure her home backfired. His first plan to get her home was to tell her he was tired and call it night. This was met with, “Have a coffee and nut up” (although again, I am paraphrasing). This is the difference between real life and the movie.  In the movies, nobody zigs when they’re supposed to zag. Everything works out. There is no “I gotta take a shit” moment in Ocean’s Eleven.

Credit: ShutterLife Productions

(This is not Luke and Michelle.) Another happy couple!  Credit: ShutterLife Productions

I am a married man, and yes, I was responsible for proposing to my (now) wife, and yes, it was a goddamn mess. It was a little over 5 years ago, and at the time Michelle and I were living together on the Upper West Side of Manhattan.  She had arranged a 30th birthday party for herself* and I knew that it was the perfect opportunity to stage our engagement.  I’d propose, she’d say yes, we’d have dinner with her awaiting family and then we’d go off to drink and celebrate with friends. It was the perfect opportunity to hide my intentions behind a veil of birthday celebration. It was Fight Night at the MGM Grand.

We had developed an interest in HGTV which led to an interest in purchasing an apartment, which led to the two of us spending hours window shopping in front of local realtors. I’m not sure what it’s like in the rest of the country, but in New York most realtors post 8 x 10 listings of available apartments in large display windows of their offices. I thought that this could work as a great setting to begin our life together (it worked on so many levels, right?) so I called a realtor near both the dinner venue and the party venue to see if I could post a fake listing in the window (i.e. “Cute male available for the rest of your life. Michelle would you marry me? blah blah blah”). They told me that they could do me one better: If I sent them the copy and an image, they would mock up a couple of slides for the Powerpoint presentation that is on a constant loop on big-screen TVs in their office windows. I said that would be great and sure enough, within a day or two they had slides ready for me. The only caveat was that the loop was 15 minutes long and my slides would only run in the loop between 7 and 8pm the night of the proposal, which meant that I would have to time it so that we arrived at exactly 7:00, 7:15, 7:30, 7:45 or 8:00, depending on when the loop began. I said fine, and came up with a lie to get Michelle in front of that screen at just the right time: I told her that we’d need to meet a friend to drop off a DVD! It was genius! Everyone needs DVDs at 7pm on a Saturday night, right? And did I mention it was outside in the middle of January? It was perfect!

So that was the plan. Get Michelle in front of the realty company just before the slide appears. While she’s reading the slide, get down on one knee and as she turns around improvise a few words about how she’s the greatest thing that’s ever happened to me and blah, blah, blah… why plan out what I’m going to say when clearly my superior intellect has created this flawless plan within a matter of days? Pssh, did Matt Damon think about what he was going to wear before the big heist?

Anyway, that was what was supposed to happen. Here is a rundown of what actually happened:

6:30 – With plenty of time to spare, I start pressuring Michelle to get out of the house. That’s when she asks if I’ve prepared the photo DVD that she asked me to make a week ago that I haven’t even started. Frantically (and covered in flop-sweat) I start making the DVD. My computer decides that this would be a perfect time to overheat and need restarting at least twice.

6:40 – Michelle sees that I’m covered in sweat and panic and says, “It’s just a dumb photo DVD. It really doesn’t matter.” to which I reply, “NO! THIS IS IMPORTANT AND EVERYTHING MUST BE PERFECT!”

6:50 – The DVD will not work and I finally accept this. We have 10 minutes to get 16 blocks and two avenues over, so we leave the apartment and hail a cab. I stress to her that it is VERY important to meet my friend John because he is very busy. She says, “Why don’t you just call him and say we’ll be late?” I reply, “NO! HE IS VERY BUSY AND THIS IS IMPORTANT AND EVERYTHING MUST BE PERFECT!” She may be starting to suspect something.

7:00 – We arrive at the realtor by cab. We are across the street from the realtor and I can see the TV and I’m praying that my slide won’t appear while we’re paying for the cab even though they’ve already told me that the slide show will start at 7pm and it’s exactly 7pm. The cab ride costs about $4. I hand him a ten-dollar bill and ask for a dollar back in change. Michelle looks at me quizzically, wondering why I’m giving him a 125% tip. I realize the error of my ways and hand him another two dollars and say, “Sorry, just give me $3 back.” Michelle just takes all the money and gives the cabbie $6. We exit the cab and I run through traffic across the street, leaving my (future) blushing bride behind me.  Alone.  Across the street.  With cars buzzing past. She, of course, waits for the light to change and casually saunters across 79th street.

7:04 – We’ve been waiting for 3 minutes in the cold and I soon realize that we’re at the very beginning of the presentation, which I would have realized long ago had I the common sense to understand the concept of time. I have also lost the ability to do any sort of math in my brain, because otherwise I would have realized that I have 11 minutes with which to stall. I also see a photographer and an executive standing in the darkened realty office, waiting for my cue. It now dawns on me that I have three people relying on the fact that I know what I’m doing instead of just the one. The flop-sweat will not stop.

7:06 – Michelle (who although having been born in the middle of winter) HATES being cold, and has not brought anything to cover her head or ears because she (logically) thinks that we will be on a 2-minute errand and doesn’t wish to alter her hair in any way. She is starting to get upset. “Just call him and ask where he is,” she says. “HE IS VERY BUSY AND THIS IS IMPORTANT AND EVERYTHING MUST BE PERFECT!” I reply. I think she thinks I have joined a cult and this is our mantra.

7:08 – I’ve come up with a great stall tactic that if I time perfectly will be remembered throughout the ages. I’ll point out an apartment listing on the wall and we’ll talk about that for at least 7 minutes. Then I’ll say, “What about this listing?” and my slide will appear. I point to a $2.5M brownstone in Harlem. “Look at this! Isn’t it amazing?” and guide her over to the listing.

7:09 – Michelle viewed the listing and replied, “We can’t afford that” and walked away from wall.

7:12 – “I’M FREEZING! PLEASE JUST CALL HIM!” she begs. “NO! HE’S VERY BUSY AND THIS IS IMPORTANT AND EVERYTHING MUST BE PERFECT!” Why wasn’t there a “Just call him!” scene in Ocean’s Eleven?

7:14 – The first slide appears. As stated earlier I had thought I would improvise a speech expressing the depths to which I love and care for this beautiful creature before me. Instead I yell out, “LOOK AT THE SCREEN! LOOK AT THE SCREEN!” She does and I get down on one knee. She looks back at me. “NOT AT ME, THE SCREEN! THE SCREEN!”

7:15 – The second slide appears. It simply says, “Michelle, will you marry me?” I’ve opened the little blue box displaying a princess cut diamond ring (please don’t ask me anything else about it; all the information I made space for in my brain on the topic of diamond rings was immediately replaced with the elaborate plan you’ve just read).

“So, will you marry me?” is the most eloquent speech I can improvise. She says yes and I place the ring on her finger and give her a very passionate kiss. I then whisper in her ear, “I had planned to give you a whole speech but I got too nervous.” This is met with another kiss that is immediately interrupted by a photographer and a robotic (although very, very kind) executive who says to us, “On behalf of Halstead Realty, we present you this bottle of champagne and wish you many years of happiness in your future together.” At least I think that’s what he said, I was in a bit of a daze. But either way, she said yes and we were married 9 months later.

Luke and Michelle and the Realty Executive post-proposal!

Luke and Michelle and the Realty Executive post-proposal!

Like I said earlier, the odds really are in your favor. With all the pomp and circumstance of the proposal, the heart of what really matters is that one person says to the other, “You’re the one I want to spend the rest of my life with,” and the other person agrees. That’s it. Or to put it in Danny Ocean terms, “When that perfect hand comes along, you bet and you bet big. Then you take the house.”

Or to put it in Billy Ocean terms, “Get out of my dreams and into my car.” (Danny wins again.)

Luke at his own wedding, with his beautiful bride. Credit: Kate Leigh

Luke and Michelle at their wedding. Credit: Kate Leigh

*Please note that Michelle had arranged her own birthday party long before I even had the opportunity. When I had asked what she wanted to do for her birthday she said, “Oh I booked a room at a bar already. I just wanted to get it out of the way.” After reading this proposal story, I leave it to you to decide if she did so out of convenience or out of fear of my planning.

Down on One Knee Photo Credit: ShutterLife Productions

Luke & Michelle Wedding Photo: Kate Leigh Photography

Reprinted with permission.