Daniel & Jennifer

On Tuesday morning at work, I made the reservations for two at Upstairs on the Square for 7:00. I mentioned to Jen that we should go out to eat with Bobby and Sabrina that night. Jen asked me if we could decide later, but telling me she wasn’t feeling up to it. The day passed slowly and for the most part, I could not concentrate on work. I left early at around 3:30 and called Jen back to confirm for dinner. But Jen had a different idea. Monday and Tuesday were two of the busiest days of the year for her, because of the annual sales meeting which she organizes. She was tired, busy and a little bit frustrated with a boyfriend who couldn’t get his act together and just ask her already. No, dinner was not meant to be. As we talked on the phone that afternoon, I just couldn’t help but laugh with her over the frustration of expecting something to happen every day and nothing to show for it. I laughed because I was holding her ring while we talked. I laughed because it would happen that night—No matter what. Finishing the conversation with a plea for patience… “Just take it one hour at a time…” I hatched Plan B.

I decided that because she was working late, I would surprise her. I showed up at her office an hour later, to her surprise. It was the first nice day of spring on Tuesday and she had just wanted to go for a walk. So I picked her up and we went out to the beach walk over in Southie. The plan was set to ask her where we first got to know each other really well— on the Avon Walk for Breast Cancer. It has begun and ended at the park, on the beach, right down the street from her office. But instead of walking, Jen’s feet were killing her from a long day running around at work, so we sat on the bench and talked about the early days and the walk and we laughed at the people running by in their too-tight spandex. I had the ring in my pocket and thought seriously about asking her right there. But there were just too many people walking by… too much of a scene. It was getting cold out there, so we headed back to the car and decide to go eat. Stopping back at her office to pick up my car, I asked her to help me with bringing my camera bag to my car. Once she was out of her car, I asked her. I asked her in the parking lot of her office because I couldn’t wait any longer. I asked her there because we were alone. I asked her there because I had no Plan C.

She said yes.

The following week came and went. Thursday night after Easter, I went back to my apartment after work and didn’t meet up with Jen just so I could brainstorm what to do. With the pressure mounting, I thought of an idea. About a month ago, I found a couple rings that I had made in high school. Each ring was made of sterling silver, and was made from two smaller rings, sautered together. The rings were approximately Jen’s size, yet unfinished. To me it made sense, two parts joined together, unfinished and unrefined, yet durable and long-lasting. I sought some advice from two wise sages— Pat and Kevin (who were having so much fun together in NYC) and tried to sell them on the idea. It didn’t fly, even with Pat. I did my best, but in the end it wasn’t enough.

Back to square one, Jen and I headed for VT on Friday to visit my parents, a seemingly perfect opportunity to ask a memorable question. Expectations were high from everyone around. No one wanted to ask the question, but everyone was waiting, and watching. And Jen came back to Boston after a fun weekend, empty-handed. Understandably, she was pretty frustrated.

But Monday was a day for redemption. I played hooky from work and did some research online. Based on my previous conversations with Jen and others, I knew what I had to do. I drove over to local Burlington, MA and went to the jewelry store that I knew would be a winner. I left with a platinum and diamond engagement ring, set and sized. Yikes! I couldn’t stop looking at that ring! The plan began to take shape that day.

Tuesday: E-Day
The stage was set. Ring in hand, the plan was as follows. Bobby, my business partner, would suggest a nice meal with him and his wife that evening. I would mention this to Jen and we would head over to a good restaurant in Harvard Square. Just before we would get to the restaurant, Bobby was set to call me and cancel at the last minute. Jen and I would then dine together in a quiet corner of the restaurant and during the meal I would propose.

Nice try…

Jen and I visited her family on Easter weekend down in Kentucky. They are wonderful people and we had a lot of fun. Her parents were there as well, and I took the opportunity to ask her father for her hand. We had a few games of pool (he won both times) and then we talked. It went well and we talked for a good 5-10 minutes before dinner was called. So we headed upstairs and the blessing was said by her grandfather. A few seconds later, her father began to say something to the family gathered in the kitchen and living room. At that point, I wasn’t quite aware of what was going on, but I slowly realized that her dad was announcing to everyone that I’d asked for Jen’s hand in marriage! Before pandaemonium broke out, I continue to watch Jen as I wasn’t sure what her reaction would be. I think the expressions that I saw were confusion, surprise and then happiness.

So, here I am, up until this point just trying to figure out the first step, and all of a sudden there are quite a few expectations on the table. The question of “When is he going to ask?” was getting louder every day on. Of course, I had no clue what I was going to do. No ring and no money, with time running against me, I had to come up with a plan…