{Always a Twist}: An Imperfect Engagement Story

The sun had set on the Eastern Shore of Maryland. I sat by a makeshift firepit next to my girlfriend’s father, Mike. The Fourth of July party at their family’s vacation home was just about over. Mike leaned over to me and said, “Greg, I give you permission to marry my daughter.”

If you were wondering, I hadn’t asked. My relationship with his daughter was serious, but not yet proposal serious.

Apparently, I’m husband material. Before I met my wife, I attended a wedding in Pittsburgh with a serious girlfriend where the bouquet and garter toss was rigged to have each of us catch them. We were still in college at the time. Two things struck me as memorable:

1. The DJ had a weird mustache. The best way to classify his facial hair style would be “the pervert.”
2. I remember thinking how odd it was for me to have to put the garter back on my barely legal girlfriend’s leg in front of her whole family.

So, parents and families had been preempting my proposal for nearly a decade. I was kind of used to it.

But my relationship with Mike’s daughter, Christina was blossoming. We dated off-and-on for a year before getting serious. Then, for 2 years, we were exclusive. (This was the period when Mike granted permission.

Around the same time, a few of her close friends were getting married, and we attended those weddings together. Once again, a garter and bouquet toss was rigged to get me and my girlfriend on the dance floor. The great football coach Vince Lombardi used to say “If you ever score a touchdown, act like you’ve been there before.” Well I had been there before, and I’ll be honest with you Vince, there is no comfortable and dignified way to handle that tradition.

Later that year, my girlfriend and I moved in together, a ritual some would say should only happen after marriage. We also worked together and shared a bank account. In my opinion, that Commitment Trifecta tied us together more than the ceremony and paperwork of marriage. As life went on, marriage seemed like a formality. We would get there, but what’s the rush?

We lived in sin together for another 2 years (that’s 6 years since we first met, if you are keeping track). We had conversations about marriage but nothing concrete. One summer evening I was performing in an improv show. The game of the show was that we were playing versions of ourselves doing a rock concert, but the band kept getting into arguments before they started to play music. Christina, had invited her uncle Chuck to the show. He had been the one that introduced us.

As the show went on, the improvisers picked on each other with issues that they knew would get a rise out of their scene partners. My friend and improv teammate, Amanda turned to me and asked, “So Greg, when are you going to propose to Christina?” For those who have seen me perform improv it’s fair to say I am quick on my feet. I can shoot back a witty response in a flash. But this question, in front of a live audience, in front of my live-in, money sharing, business partner girlfriend and the man who introduced us, this question stopped me flat. In that moment a rush of thoughts went through my head:

Am I proposing right now? No, no, I hadn’t planned this.

But is this a happy accident? Should I grab life by the horns right now and propose?

No. There is nothing romantic about interrupting a show people paid money to see and forcing your girlfriend make a life long decision.

So I did what any great performer does when they are uncomfortable, change the topic and hope no one brings it up again. Luckily, I made it through the rest of the show without having to confront the question.

But now, I had a big issue on my hands. I almost accidentally proposed to my girlfriend. She recognized it too. As my thoughts confirmed, receiving a wedding proposal during an improv show was not high on her list. We began talking in earnest about marriage.

Christina and I shared a love for movies. Romantic comedies to be exact and I wanted to make sure my proposal would stand up against anything you would see on the big screen. There are three elements to a great proposal.

1. The ring
2. The location
3. The words

I found out the ring she wanted was at Tiffany’s. It was a dream of hers to get that light blue box.

I started researching locations to do the proposal. I decided on the National Cathedral. It’s a landmark you can see from lots of locations in the city and it would be a bonus to have its sightings have personal significance. A client of mine worked there and he suggested the Bishop’s Garden, a perfectly manicured area with seasonal flowers and fauna.

The final item to lock down was the actual words I would say to Christina. I tapped into the greatest artistic minds I could find, Leonardo, Shakespeare, and Thomas. I of course am referring to Leonardo DiCaprio in Titanic, Joseph Feinnes in Shakespeare in Love, and Thomas Cruise as Jerry Maguire. It took draft after draft, but I finally wrote something I was proud of.

My plan was ready to go by Friday night. Saturday I would go to Tiffany to get the ring. Sunday I would propose at the Cathedral. Immediately after the proposal, we would leave D.C. to visit friends in New York, then family in Maryland and Florida. I imagined a congratulations tour of all our closest loved ones. I went to sleep beaming with my logistical prowess. Nothing could go wrong.

I awoke to 3 feet of snow covering Washington, D.C. My car was completely snowed in. Metro had shut down all above-ground stations. The city was at a standstill, and I had a pretty crucial purchase to make. Mother Nature be damned, I was getting that ring. Luckily, Tiffany is located at the last underground Metro station on the Red Line.

But my winter wardrobe was not prepared for 3 feet of snow. I did the best I could. I wore a pair of pajama pants under some old jeans. A thick pair of socks covered with a plastic shopping bag, covered by a pair of boots. A hooded sweatshirt and a pea coat. Finally, a giant faux fur hat I had bought as a joke at Abercrombie & Fitch in college. In short, I looked like a hobo as I tramped through the snow swells to the Metro.

As I rode the train, I played out what might happen at Tiffany’s when I arrive. I flash to the scene in Pretty Woman where the store gives her bad service because of how she looks. So, I swung the door open and prepared to show them I deserved to be there. My build up was completely unfounded. Tiffany’s didn’t give a crap about how I looked. They immediately gave me five-star service. It’s nice to know every hobo with cash has a shot at Tiffany’s.

Once I emptied my bank account, they gave me the ring in that renowned blue bag. I walked back to the Metro and immediately became Gollum from The Lord of the Rings. I had my precious ring and I thought every Metro rider was out to get it. All I wanted was to get home and hide it in my closet.

Once the ring was safe, I still couldn’t shake the feeling of unease. My perfect proposal plans were coming off the rails. I was on edge from protecting the ring on my Metro ride. The realization that I was actually going to propose marriage made me jittery.

That afternoon, Christina was packing for our trip to New York and she said, “Wouldn’t it be nice to get some insulating spandex pants to go under our jeans while we walk through the city? I found some pairs for $75.00 each.” It was a completely reasonable request. Heck, I wore ratty old pajamas under my pants that morning to go in the snow. The tension of the moment got to me and I snapped. “No! We don’t need any spandex pants. It’s a waste of money.” Christina crossed her arms and went to her side of the room. I crossed my arms and went to my side of the room.

My marriage hadn’t even started yet, and it was already in trouble over spandex pants. Spandex pants! I took a deep breath and apologized. I realized the way I proposed wasn’t the important part. The way I treated Christina with love every day was the important part.

The next morning we drove to the Cathedral with the ring hidden in my coat pocket. The place I had planned to park was of course still covered in snow. I drove around to another garage. The Bishop’s Garden was of course covered in snow. I took Christina to the front right side of the Cathedral. I threw away the speech that would have made Leo, Shakespeare, and Jerry Maguire shed a tear. I got down on one knee and from my heart said, “I don’t want to go another day without knowing you’ll be with me forever. Will you marry me?”

Christina gleefully said yes. I asked again to be sure. Her second answer was also yes. I put the ring on her finger to make it official. Talk about your Commitment Trifecta.

It turned out to be the perfect surprise proposal. OK, it wasn’t a big surprise. When I tried to buy the ring at Tiffany’s, I used a credit card that had a daily maximum less than the cost of the ring, so I had to use our joint account to pay the other half. So I changed the password to our bank account and told her not to look because I got her something for Christmas. Then when I told her I had to stop by the Cathedral for work before heading to New York, she could tell something was up. God bless her for just keeping her mouth closed and letting me pretend I was being covert.

So it wasn’t the perfect proposal. But it was the perfect proposal for us. I had just one request for the wedding: no throwing a garter belt.