Jessica and Jay

How we met: Being a new single Mom, the idea of dating was scary and how and where to meet people was even scarier. With the encouragement of a really great friend, I tried dating in the online world. My first stop was After a couple of uncomfortable first dates and even more uncomfortable “messages” from people, I took a break from Match. On a side note, the really great friend met his now fiancé on Match and they are getting married next year! :) Another friend who met her now husband online, further encouraged me to try online dating and try I signed up for the “free weekend” in November 2012 and that same weekend I received a message from Jay. After exchanging a few messages, plus he was cute and from Seattle (an added bonus), we finally agreed to meet. Two single, working parents, how hard could it be to arrange a first date? After a week of trying to fit me into his busy schedule, and me thinking he was too busy to date, we finally settle on meeting for a drink at The Deck in Laguna Beach the Sunday after Thanksgiving. That Sunday also happened to be the day after my 10-year high school reunion. Lets just say had a good night!

Our first date at The Deck was November 25, 2012 at sunset. I remember being really excited, nervous, and self-conscious. Self-conscious mainly because most people who meet me for the first time think I look 18. That feeling was not helped by the “cougars” eyeing my date! Meeting Jay for the first time was kind of a blur. I remembering thinking how handsome he was (he looked like his picture!), his white shirt, I believe he ordered a Mai Tai, and the sunset was directly in my eyes. We had the normal getting to know you conversation. There were, however, a lot of coincidences in how we grew up and the most fascinating one being, Jay shared the same birthday as Madison! I left that date feeling super excited and looking forward to the next one!

how they asked: Jay and I had talked about getting married for a few months. We had been ring shopping and he made a couple of secret trips to Downtown LA. He had also asked my Dad’s permission (twice). So I knew a proposal was coming I just didn’t know when. And since I didn’t want to get my hopes up of when and where it would happen, I put the idea in the back of my mind.

We went on a second trip to Seattle over Labor Day Weekend for a second wedding in eight days. Looking back on the days leading up to the proposal there were a ton of clues, I just didn’t catch any of them. It started with the first class upgrade and a rental of a BMW 5 Series- not totally out of the norm of how Jay likes to travel, but a missed clue. While I ran errands downtown, Jay went to the hotel to get us checked in. When I finally got to the hotel, the front desk girl was overly excited to see me, again another missed clue. While we were getting ready for the wedding, the front desk called and wanted to speak to Jay but didn’t want to leave me the message. When Jay called back he said they wanted to know when we were leaving for turndown service- I thought that was strange and why couldn’t the girl just ask me. The next day, Saturday, I had planned a day in the city before we went to the Mariners game. Jay kept insisting on an hour of the morning to go drive somewhere, but he wouldn’t tell me. When we finally got in the car he said we were going to take a drive to my old hometown of Kent since he’d never really been there before. Again, I didn’t think anything of it since I had suggested the same idea for Sunday.

We drive up to my old neighborhood, convince the guard to let us in and make our way to my old childhood home. At this point I am already nostalgic and sad, and starting to get emotional. Jay wants to get out of the car and take a picture but I refuse. After bantering back and fourth (I swear he was about to say, “Woman! Get out of the car!”), Jay finally just gets out of the car and I reluctantly follow. I get in position to take a selfie when Jay suggest that we flag down a car to get someone to take our picture. I think he’s insane! Somehow he gets a random girl to stop and take our picture. Unknown to me, he actually sets up his phone on video. I get in position again to take a picture while Jay turns towards me and eventually gets down on one knee and asks me to marry him!

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We both spent the rest of the weekend in what was really a euphoric haze. And, thank you to my Dad for calling in a favor six hours later at the Mariners’ game, congratulating us on our engagement the same day of our engagement!