MaryAnn and Derek

Image 10 of MaryAnn and Derek

How We Met

Derek and I met 5 years ago, in 2015, at a music festival meeting. He was the Director and I was the Staff Coordinator. We were seeing other people at the time but grew friendly throughout the meetings and the festivals themselves. During our 3rd year working together, 2017, I looked forward to each of the meetings and events because I was excited to see him, I never shared this, of course.

Image 1 of MaryAnn and Derek

During that year, with both of us recently single, Derek actually flirted with me quite a bit, but I shot him down a few times! We took our first photo together that year, one of us sharing a Malibu bucket after a particularly difficult festival day, and although that moment made me realized I really enjoyed being around him, I still couldn’t bring myself to hang out with him one on one. Once our festival season ended, we texted a bit, but the conversation died for a few months.

Image 2 of MaryAnn and Derek


The following year, 2018, I had recently moved to a new city, and I received a text from one of our mutual friends that he and Derek were at a bar downtown. I dragged my roommate out with me so I wouldn’t show up alone. Derek and I instantly reconnected and started flirting heavily.

Image 3 of MaryAnn and Derek

We went on our first date on June 1, 2018, and officially became boyfriend/girlfriend on June 19, 2018. We’ve had so many wonderful adventures since then. We moved in together in November of 2019, we have 3 fur babies, and I have loved every moment of being in love with him.

Image 4 of MaryAnn and Derek

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Image 7 of MaryAnn and Derek

How They Asked

Derek had been talking about getting together with his friends at a restaurant all week. I was actually a bit leary because of the recent COVID spikes but agreed to go.

Because we had been talking about engagement and marriage frequently, I knew it was coming but didn’t know exactly when. So I made sure to look nice every time we went out.

We made plans to meet his friends at the restaurant where we had our first date, it’s a cute waterside restaurant with outside dining. I had an inkling because of the location but dismissed it because I didn’t think he would propose in front of all of his friends.

Image 8 of MaryAnn and Derek

Before we left, Derek made sure to grab a t-shirt that he was returning to one of his friends. I didn’t think anything of it. On the drive down, we received a call saying they were running a few minutes late, again, nothing out of the ordinary.

Once we parked, we started walking out of the parking lot when Derek remembered the shirt and ran back to his car. The thought crossed my mind of, “lol maybe he’s grabbing a ring,” but again, I didn’t want to get my hopes up. He looked like he was digging around in his car, so as he walked back I did a once over to see if I could spot a ring box, no luck, so I pushed the thought from my mind.

Image 9 of MaryAnn and Derek

As we walked toward the hostess stand, I asked if we could check-in or if we needed the whole party. Derek insisted we needed the whole party and then suggested a walk by the water, something we did on our first date.

As we were walking we talked about the boats there and then conversation led to our families. Derek made a remark about how he hopes my family likes him, and I told them they did. Then he said, “Well your father was pretty welcoming when I asked for his blessing the other day.” I shot him a look like, “yeah right, you didn’t go over there.” Then he opened the t-shirt where a pretty blue ring box was sitting!

Image 11 of MaryAnn and Derek

The first words out of my mouth were actually, “oh no,” I was so in shock!

He said some very romantic words then got down on his knee and asked me to marry him. One of our mutual friends (the same one that texted me that night 2 years ago!) popped out of the bushes to take pictures. I said yes and cried A LOT! The people sitting in the outside dining a bit behind us had watched the whole thing and started cheering.

The plot of meeting his friends for dinner, needing to return the t-shirt, and even the phone call of his friends being late were all fake! He really had me convinced this was going to be an ordinary night and I’m so glad it wasn’t!

I’m so excited to spend the rest of my life with the love of my life!

Image 12 of MaryAnn and Derek

The ring is literally my dream ring. It is a solitaire diamond on a Platinum band from Tiffany & Co.