Sydney and Caleb

How We Met

Caleb and I have known each other since 2008(ish). We went to the same high school in a very small town where everybody knew everybody (one of those one stoplight/one gas station kinds). He had lived in the town his whole life, but I moved just before starting high school. We didn’t begin to form a friendship until my second year of high school. We were involved in a lot of the same activities and we shared the same friends…so it was inevitable that we would spend a lot of time together. Our relationship developed slowly, starting with casual conversations in the library before school, hanging out at friend’s houses on the weekend, and prom my Junior year. I think that that was the turning point for me. I began to realize that I had feelings for him as more than just a friend.

Wedding Proposal Ideas in Messina Hof Winery

Fast forward through the summer to the beginning of my senior year and his junior (he was a grade behind me). My feelings started to develop more and more, but I just couldn’t figure out where his head was. It wasn’t until the beginning of January in 2011 that we really started spending time together as more than friends. This started as a kind of disastrous double date (sparing you all of the details…it involved a set of friends that weren’t even dating as the other couple, a friends emotional breakdown in the mall and a sold out movie). Thankfully that didn’t scare either of us away and we began courting soon after. He asked me to my Senior prom, bought me the most precious Valentine’s day gift and finally made our relationship official over Spring break in March of 2011! It was definitely a long road, but all of the time we spent getting to know each other as friends beforehand really did help our relationship to flourish!

How He Asked

Since we have been together for so long, obviously the discussion of marriage and our future had come up quite a bit, especially in recent years. We would discuss and plan and think about it often, but we knew that marriage was not going to happen until we were both done with College. I graduated in 2016, but since Caleb was in engineering, he took a bit of a longer route and wasn’t finished until May of this year. The discussions got more and more serious about engagement and marriage, but I had been suspicious of a proposal several times over the past year and it hadn’t happened, so I had resolved that he wasn’t yet planning to ask. That is where I was wrong.

The morning of the proposal started out pretty normal. We woke up, Caleb cooked breakfast and we hung out lazily in the living room while I made him watch Gossip Girl with me for the 500th time. He was moving out of his town home this weekend, so he had plans to pack all day (as far as I knew). My best friend, Jessica, was coming in to town that day and she had asked me weeks prior to go to the local winery with her for a wine tasting that we had wanted to do for forever. I had agreed, but for some reason I wasn’t exactly feeling like going that morning. When she got to the house, she was a bit distraught because I wasn’t ready to leave yet. I didn’t think anything of this because she and I are both pretty dramatic by nature. I voiced to her that I wasn’t sure I wanted to go to the winery and she, of course, convinced me to go. Caleb left and I got dressed and ready, and we headed out.

She wanted to go to the winery right away, but I suggested that we stop by Target (our fav place on the planet) first. She told me later that she was freaking out internally because we were supposed to be on a ‘schedule’ but I had no idea. She kept her cool and was patient with me. They definitely knew I had NO idea what was coming, because I am usually a stickler about being early/on time to things.

When we finally got to the winery we paid for the wine tour that we of course were not going on, and then get to the bar to buy a glass to drink. Jessica began asking for photo op suggestions which is, again, not unlike her. She loves any excuse to take photos! The lady at the bar suggested a few locations, but said ‘you have to check out the gazebo. It’s the best place for photos’. So we headed down the trail to the gazebo. We were sipping our wine and talking when all of a sudden Jessica said ‘look to your left’. I looked back over my shoulder and saw nothing. I was about to ask her what she was talking about when all of a sudden I caught a glimpse of a light grey suit near the gazebo. I looked up and there stood Caleb all dressed up and waiting. I WAS SPEECHLESS.

I walked over to him and I kept saying ‘what the heck’ ‘what the heck’ over and over again. He walked me over to the gazebo and positioned me in front of him. He then began talking sweetly and eventually got down on one knee.

I’m honestly not even 100% sure what he said because I was so shocked that this was actually happening! I, of course, said yes and then he turned me and said ‘look over there. do you recognize that photographer?’. I looked a little closer and it was my sister! She is a photographer in Colorado, and he had gotten her to come to Texas so that she could be the one photographing this special occasion! How special is that?

Sydney's Proposal in Messina Hof Winery

Later on in the evening, he surprised me, yet again, with a house full of friends and family (both local and out of towners) at his place to celebrate the engagement! It was an amazing day full of happy tears, a ton of photos and lots of love!

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After the fact, I found out he had purchased the ring in January, and had been planning the engagement for 6 MONTHS! I never would’ve guessed that he (and everyone involved) could’ve kept the secret that long. I am usually SO hard to surprise! But I am so thankful that I was surprised and had no clue it was happening when it did…that made it all the more special!

Special Thanks

Howard-Crow Photography
Photographer