Whether you decide to propose at a Yankee Game, on top of the Eiffel Tower, or on your couch with a home cooked meal, chances are that you want it to be a surprise. However, by the time you are ready to propose, your significant other has probably already sniffed you out. Her inner Nancy Drew emerges and she (or he) begins looking and listening for anything out of the ordinary. For me, since my girlfriend already knew that the coveted ring was being made (see “The Ring”), my chances of orchestrating a successful surprise were basically slim to none.
I had a fairly simple plan of how I wanted to propose. I knew I was going to do it at our favorite restaurant, where we had our first date, and I knew I wanted both of our families to be there. After coordinating with everyone and setting a date, I needed to make sure that my girlfriend would be available. I created a fake email address that resembled a wedding vendor and sent an invite email to myself for a “work event,” which just so happened to be located in the same neighborhood as our favorite restaurant. I then forwarded the email to my girlfriend asking her if she would like to go with me. The work event was a perfect cover, it even gave me an excuse to dress nicely without raising suspicions (I like pajama pants). After she said yes, I casually mentioned that we should grab a glass of wine at our favorite restaurant first, and then spent the next hour patting myself on the back for being so creative and tricking her. Then I got the email from her mom…
Apparently, my girlfriend was on to me and she had emailed her mom saying so. I immediately implemented Operation MAMPAP (Make as many plans as possible). “Dane Cook is playing at the Garden. He almost made me laugh once, we gotta go see him.” Springsteen at Giants Stadium, Pearl Jam in Philly, pigeon feeding in Central Park, etc. I even threw in a plan to go ice skating at Rockefeller Center for a friends birthday in December in hopes of diverting her suspicions.
Finally, the big day arrived and I was ready to sit across the table from her and spit out a whole speech that I had prepared in my head. But when the moment finally came, I froze and omitted about 75% of my spiel. Not to mention that there was not much space between each table in the restaurant, and when I dropped down on one knee, it felt awkward and clumsy to say the least. Then, I was on one knee for what seemed like an eternity and eventually had to ask her to answer me before she said yes. But if I had to describe the night in one word…it was perfect.
I guess the moral of my story is that it does not matter whether your plan is thrown a little off kilter, or whether your girlfriend suddenly morphs into an arguably crazy, modern-day Sherlock Holmes—it is a joyous occasion and the only important thing is to have fun with it. I barely remember what I said before I gave her the ring, but I will never forget all of the stupid things that I said and did to try and trick her, the secret emails with her mom, planning a surprise vacation to celebrate, and the entire experience as a whole.
So, now I’m engaged, and we have a wedding to plan. Let the fun begin……
[EDITOR'S NOTE: JASON REALLY DOES PREFER PAJAMA PANTS. SEE BELOW.]























