How To Propose?

By: Heather Somaini

I needed to come up with something thoughtful and amazing to propose to Tere.  Since we officially met on Christmas day, I knew it had to be in connection with the holidays.  Our family was celebrating Christmas that year at my grandmother’s home in Port Charlotte, Florida.  I decided we would fly up to New York City and I would propose there.  It’s one of our favorite cities and I had a friend, Jill, who could help me with my plan.  I also really liked to keep Tere guessing and generally pulling the rug out from under her as often as possible.  I know; I’m mean-spirited, but it’s really soooo much fun!  And because I’m confident that Tere understands it – just like a little girl knows that a boy likes her when he pulls her ponytail – I’m justified.

My grand idea was this: a gigantic scavenger hunt from Florida to New York culminating in the aforesaid proposal in the city that never sleeps.  At every opportunity for Tere to assume a payoff was coming, I would throw her a curveball.

Here was my plan:

The kick-off would happen on Christmas afternoon, when we would exchange anniversary cards.  Mine would include a clue in the form of a silly poem that we were going somewhere that very night. I knew she would pepper me with questions along the way to the airport, so my goal was to give up nothing until we reached the gate and she’d figure out that our destination was NYC.  While in-flight, I would give Tere another clue as to our upcoming activities.  Once we landed, we would take a cab to the Omni Berkshire Hotel.  We would drop off our bags and then take a late night stroll over to Rockefeller Center to see the Christmas tree, along with a few of the high-end department store window displays.  Seeing the Christmas tree was on Tere’s life to-do list, so: check one off!

The next morning, breakfast would be delivered to the room where Tere would receive a new clue and the first section of a custom-made “proposal puzzle”.  I had broken the puzzle into sections so that she wouldn’t know what it was until the very last piece was in place.

Upon reading the clue and completing Puzzle Section #1, she would realize we were going on a carriage ride in Central Park.  At the end of the carriage ride, the driver would give Tere a new clue about skating in Rockefeller Center (also on Tere’s life to-do list) and Puzzle Section #2.

After ice-skating, the “skate girl” would give Tere a clue about our favorite chocolatier, Richart, and the third section of the puzzle.

The salesperson at Richart would give Tere Puzzle Section #4 and yet another clue.

A lovely lunch would follow where Tere would receive Puzzle Section #5 and – you guessed it – a clue from the waitress.

By now, it would be late in the afternoon and off we’d go for drinks at the Rainbow Room. There I would give her another clue as well as Puzzle Section #6.   Back at the hotel, where we would go so Tere could finish the puzzle, hid another clue, which led to a wooden puzzle box.

As you can see it’s not what she would be expecting. The clue was wrapped in something heavy so it would rattle when she opened it.  She would think there was a ring inside – a perfect disappointment for Tere!  The wooden puzzle box is super-complicated and requires a good bit of trial and error to open.  It holds the last clue -dinner at Thom at 60 Thompson.

During dinner, while Tere is now absolutely expecting a ring, I will give her a necklace.  I know: mean!  We will have an after-dinner drink where will I give Tere a proposal poem that I’ve written and, finally, THE RING.

That was it; that was my plan.

There’s a thing about plans though:  sometimes they just don’t go the way they’re supposed to.  “The best laid plans of mice and men often go astray.”

My plan was about to go terribly astray.

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