The Proposal in the Park

"Jackie, I would like to propose to your sister."

And that is where it all began. When Shane told me that he wanted to propose to my sister, April, I was confused as to why he was telling me. He and April went out for dinner together to celebrate her new job and he started this conversation as soon as she went out for a phone call. Later on, I found out that I was the first person he told. Although Shane and April were not the most traditional couple out there, I was surprised that he did not ask my father for permission first. April and Shane had been together for almost five years at that point, so I suppose that everyone was waiting patiently for him to pop the question.

I must have looked confused when I turned to him and asked, "Why are you telling me?"

Shane laughed and sarcastically said, "It's great to hear that you are excited!"

"Shane, don't get me wrong, I am super happy for you both. That is great news." I paused and pondered how to continue. Congratulating him was probably the most proper answer, but I was dumbfounded by his statement. He did not sound nervous at all about revealing the news, it was the exact opposite of that. He sounded as if he needed a favor or something from me. "You just sounded weird when you told me. Did she pressure you into this?"

"No, not at all." His denial was clearly genuine and I believed him, but I still knew something was going on. Shane and I were never particularly close, despite knowing each other for years.

I rubbed my forehead and as politely as possible, I asked, "Then what is going on? Do you need something from me?"

He smiled, pointed at me, and declared, "Aha, you are smarter than what I thought!"

I cautioned, "Don't push it, Shane. If you need help, you'll need to kiss my--"

He interrupted, "Sorry, I apologize. I'll be nicer about this. After all, I am asking you for a favor."

I glared at him and demanded, "Just tell me what you need. April might be coming back any second now."

"You know April better than anyone. Heck, you know her better than me. So you should be able to help me plan the perfect proposal. I need you to brainstorm and tell me any ideas that you can think of. I need a plan and a place. I'll take her to the perfect place and try my best to do this perfectly. It'll be like a dream."

As he was talking, I realized that he was right. If anyone knew April the best, that had to have been me. I knew a lot about her and a lot about how much of a hopeless romantic she was. She always talked about how she wanted to find her prince charming and apparently, for some strange reason, Shane was her dream guy. Somewhat reluctantly, I agreed to help him. Unfortunately for me, in the end, Shane seemed to dump all the work on me. It seemed like I would do everything except the proposing. Every time I had an idea, I made sure to run it by him. His response was always something like "that sounds great", which was not at all helpful. I tried my best to indiscreetly find out what my sister envisioned for a proposal. Although it was very unpleasant for me, we watched a lot of romantic comedies together, almost all of which had proposals. When watching each movie, I asked her random questions about which dates and proposals she liked best.

The first time, she gushed, "Oh my gosh, I love how they do this. It's in the rain and it's also a miracle that the ring and its box weren't damaged from it. Rain makes everything either super sad, dramatic, or romantic."

I made a mental note that a casual, rainy day would be the perfect setting. Then she mentioned how lovely a proposal would be on a sunny day in Venice while on the water. Over the years, I had always said she was the most indecisive person I knew. That indecisiveness drove me crazy. More and more ideas for proposals were mentioned over time, all of which contradicted at least one of the other ideas. For ideal locations, besides Venice, she mentioned where the two first met, Paris, New York City, Los Angeles, Montreal, Tokyo, along with multiple other places. With each new location, I let Shane know whatever she had told me. Paris was the last place I had mentioned and led to perhaps one of the least helpful phone calls I have ever had.