how we met
It was the summer of 2012. I was living in Santa Monica, California. I was spending my weekends going to crowded bars and my weekdays on bad first dates with random women from the internet. I had begun to consider myself an internet dating guru. Not because I had some magical ability to make girls fall in love with me, but because I had gotten pretty good at getting fast, frugal, first dates (I was certainly well aware of the fact that my single status probably served as proof that I needed some serious help once I actually met these women). Anyway, I had a template that I sent out in bulk. Carpet bombing, I called it. Cut, paste, customize, send. I didn’t put a ton of thought into which women I messaged and I’d often get responses from women whom I really shouldn’t have messaged in the first place. Like a lot of people, I always believed that I was most likely to meet my wife in the real world, so I did my best to make sure that the internet wasn’t the only place I was meeting potential wives, but the good thing about internet dating is that you almost always have something in the works. I had learned that I was happy enough being single as long as I had some hope, and internet dating did a great job of filling in the gaps of “real-world prospects” hope.
This one day, probably the day after another carpet bombing session, I got a response from a girl, Elsa, who grew up in Minnesota and Wisconsin. I’m from Maine and I always envisioned myself marrying someone from somewhere cold — it certainly was never a prerequisite but always a plus. Elsa had quite a few pictures and looked really pretty in all of them. I read her profile closely (admittedly for the first time) and she seemed really great. There were no bad jokes. No trashy pictures. No modeling shots (truth be told, I had a quasi-modeling shot in my profile….long story but…whatever). The point is that she seemed like a real catch. Having said that, after five or so years of internet dating, I knew enough to know that there was a 99.9% chance that this girl wasn’t as great as she seemed. To protect my time, my wallet, and my heart, my standard routine was to try to transition as quickly as possible from first internet response to first date. But due to scheduling conflicts (I was in Maine and she was in Minnesota), we ended up chatting on the phone for about 3 weeks before we actually met. So I was uncharacteristically excited about this first date. When I did finally meet her and realized that…wait for it…she was everything I had been hoping for and more, I was pretty fired up.
how they asked
When I first started thinking about how I wanted to propose, my only goal was to do something that would be meaningful to Elsa. I didn’t want to just pick a romantic place on a beach or surprise her with a ring on some international monument — I wanted to do something that showed some thought and some effort. Elsa is a preschool teacher at Piper Preschool in Santa Monica and since she absolutely loves her job, her school, and her colleagues, I felt like it would be meaningful to her if I found some way to involve her school. I thought about having the kids (most of whom are between four and four and a half years old) hold up some sort of sign on cue å la Meet the Parents, but then I thought 1. that’s lame to do the same thing Ben Stiller did in a movie and, 2. there’s zero chance that a bunch of four-year olds could be counted on to do anything on cue. Then, truth be told, my good friend, Christine Ryan, suggested I write Elsa a children’s book. Up until this point, I’ve taken full credit for this idea but I think I’m ready for credit to be properly dispensed. Keep in mind, however, that Christine owed me big time because I set her up on a blind date with her now husband. Anyway, I loved the book idea. So now I just needed to buy the perfect diamond/ring, write a children’s book, illustrate a children’s book, and figure out how to “present” this children’s book at her school.
The first thing I had to do was to get permission from her school. Fearing that Elsa would kill me if she ever found out, I reached out to Crystal, the Director of Piper Preschool and arranged a super secret coffee meeting in Santa Monica. I told her my idea and that I was worried it might not be appropriate to do all this in front of a bunch of kids. Crystal was amazing — she assured me that it was appropriate and that she’d do everything she could to help make it work.
I had decided that this was going to happen right before Thanksgiving so that we would be able to celebrate our engagement with our friends and family over Thanksgiving. The latter part to this plan was easier said than done. She was planning to go to Minnesota to spend Thanksgiving with her family and then to Nashville to see her friends for the weekend. Without her knowing it, I managed to change her Thanksgiving plans and put both of us on a flight to Boston to see my family and then to Minnesota to see her family. As for her Nashville friends, they were nice enough to book flights to LA to celebrate with us post-proposal. The end result of all these flight changes was that I now had a hard deadline — everything needed to be done and ready by November 23rd.
Obviously, the book was the hardest part here. My good friend, John D’Arco. was a huge help with this entire project. He smartly suggested that I make the story rhyme. We both decided that a lobster would be an appropriate protagonist because I’m from Maine. No, we didn’t really think about the “lobsters mate for life” thing from Friends but I suppose that’s a convenient coincidence. After about 25 different drafts with John, I finally had the story written out. To illustrate it, I went through each page of the book and sketched a corresponding drawing in pencil. I took a picture of the drawing, uploaded the picture to my computer, imported the drawing into photoshop, then used photoshop to “paint” within the lines. It looked a bit messy but I felt as though it looked intentionally messy so I was fine with it. Once I finished the drawings, I had everything ready to go but I still needed to find a way to create the actual book and have it look like a real book. I cofounded a coupon website called promocodesforyou.com and I knew that one of our clients, Mixbook.com, would allow me to do exactly what I wanted to do. It wasn’t all that hard for me to upload my drawings, add the words of the story, and order a copy on Mixbook.
Now, how was this all going to play out? I needed a plan — preferably a plan that minimized unexpected outcomes. Elsa often mentioned that she’d love it if I came to her class to read to her kids or to play a game with them. Maybe I’d show up one time to read a “normal” book (just to throw her off the scent) and then the second time I’d come in hot with the “proposal” book? But something about that felt too soft to me. I wanted it to be more dramatic. More of a surprise. I also knew that I wanted to film this. So I decided that I could have Crystal ask Elsa to read a book for “marketing purposes” and that I would be disguised as one of two camera men who were filming while she read. Finally, at the end of the book, I’d move in for the close-up shot and rip off my disguise. Great plan, right?
Cut to: me at a professional costume designer’s house in Glendale. John D’Arco came along and supervised as this nice, talented woman glued a beard to my face and gave me bushy eyebrows. Feeling pretty good about the look, I wore it back to my office to see if I could trick my colleagues. It didn’t work. Not even close. They thought I just looked like a much creepier version of myself and that if, by some miracle the school didn’t have me arrested upon entering, there was zero chance Elsa wouldn’t recognize me in 30 seconds. Okay….time for plan B. Order a lobster costume off of Amazon. That was sort of the back-pocket idea all along.
When the ring and the book and the lobster costume had all arrived, all was left was to coordinate the little details with Crystal and Jesse (Crystal’s husband and co-owner who would be filming). I had so many concerns. Would Elsa believe that they were filming her for marketing purposes? Wouldn’t she want to read the book beforehand? If she saw the “Will you marry me?” page at the end would she suspect what was actually going on? (Note: despite how it appeared in the video, there was a final page that showed Bobster proposing…Elsa just accidentally skipped it). How would I know when to enter the room? Crystal and Jesse calmed my nerves and told me that Elsa wouldn’t be suspicious. They were going to give her the book at the last minute so she couldn’t flip through it.
Soon enough it was November 23rd and I was sitting in Jesse’s office wearing a lobster costume. For some reason, I underestimated how awkward this would be. A really nice woman at Piper, Cindy Knight, then told me that Jesse was almost ready for me. She led me to my hiding spot on the stairs. Now, this spot was well hidden from Elsa but it was not at all hidden from the hordes of children following their teachers around the school. Needless to say, I didn’t exactly fit right in with my lobster costume on. After what seemed like two sweaty hours, Cindy gave me the sign — “You’re on.”
Claws shaking, I busted through the classroom door. Not surprisingly, everyone turned and stared at me. Someone said, “It’s Bobster!” but I heard nothing. While there were eighteen kids and five adults in the room (including Crystal and Jesse) I didn’t look directly at anyone. I knew I had to get on a knee and say, “Will you marry me?” so I was focused on not screwing that up. If you watch the video, you can see that my tail wiped out one of the little kiddoes as I made my way to Elsa. Sorry pal.
Annnnnnd….I did it. She said yes (even though that fact has been called into question from people who have watched the video…she said it! It was just quiet). It wasn’t until we walked out of the room that I realized that it was a huge success. She was surprised and she was thrilled (and she seemed to genuinely love the ring which was a relief).
About a day later, Jesse sent over the video footage. Elsa posted the video on youtube and facebook, and within a week, I had been contacted by ABC News, Today.com, and a TV show called RightThisMinute. A few weeks later Ashton Kutcher posted it on his Facebook page. Getting all that attention was fun for both of us.
One other thing to note: If you watch the video, you might notice that Elsa’s hair looked pretty darn good. By some miracle, she had gotten her hair done the day before. Does this seem a bit too convenient anybody else? Hmmmm.