I had a really hard time figuring out how to propose to Andrea and I went through a variety of ideas before the “right one” hit me.

1. Alaska

In retrospect, life would have been a lot easier had I just “got it over with” on the Alaskan cruise. It was a gorgeous setting and we were with Andrea’s family. The only reason I shot this one down was because I thought it was a bit too obvious. I could just imagine Andrea and her nurse coworkers discussing the topic. Amy Richards might say, “Oh he’s definitely going to do it on the cruise”. I don’t like to be predictable when I’m pulling a surprise, usually, so Alaska was out.

2. Stow Lake

Andrea repeats things from time to time. She doesn’t think I’ve caught on to this but I know it’s intentional and purposeful. One of those things is about how nice it would be to take a row boat out onto Stow Lake in Golden Gate Park. Thinking this might be the place, I convinced friend Eric to come with me and recon the area for a potential proposal. Despite the idyllic setting a row boat on a lake in the park might sound, we found the boathouse to be slightly run down, the boats aged and rusting, and the water a bit funky. Oh, and that whole rowing the boat while trying to not act nervous would definitely not have worked out. So to Andrea: yes, we can go here sometime, I’m listening, but sorry, not the place for me to propose.

3. Cupid’s Span

About two months before I had even bought the ring, Andrea and I were walking along the Embarcadero from our apartment, along the water past the AT&T Ballpark towards one of our favorite restaurants, Taylors (now called Gotts). Halfway along the way there is a giant sculpture of a bow and arrow, with the arrow facing the ground. The spot is called Cupid’s Span and it would be a very cheesy place to propose. So on that day, I proclaimed to Andrea that I would someday ask her to marry me at this precise location. I knew I wouldn’t but it resulted in my desired effect; every time we passed that spot over the next six months, her heart maybe raced just a little bit more, wondering, “Is this the time”.

4. On a website

Even before I proposed and likely as a sign either that I needed to hurry up or that she was on to me, Andrea began browsing modern wedding websites. Of these, and a really great site, is Green Wedding Shoes (greenweddingshoes.com). After I had already decided to make the photograph collage video proposal, I began to wonder how I could surprise Andrea with it. It occurred to me that Andrea would be incredibly shocked if I could somehow get the video on the wedding site. I sent an email to the site’s editor thinking I didn’t have a chance….and she responded, but the idea seemed a bit too public for me. I wanted the engagement to be about us, be private, special, memorable, not shared with thousands of strangers, and decided against it.

5. Using Skype

This idea would have made a great commercial for Skype. Because Andrea and I live so far from our families and loved ones, we often use Skype as a way to see and talk to family from time to time. My idea was that during one of these video sessions with Andrea’s family, I would have them feed her the link. She would watch the video on her computer and her family would be watching her (and maybe us) through the Skype video feed and see the proposal and her reaction the video. I really liked this idea – it would be a way to include family even more and they could “be there” when it happened. Two problems came up as I planned this. First, I didn’t want to propose in our apartment. Given this is the only place we’ve ever Skype’d our families, it was given that Andrea might think something is up if I pulled out the laptop anyplace else. Second, if I wasn’t going to do it in the apartment, then we’d need a reliable internet connection wherever it was that I decided on. Starbucks? Work? Yeah, that wasn’t going to happen.

Tim