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The Engagement

January 13, 2022 /

The Perfect Proposal by Kristen

August 15th, 2021 was definitely the best day of my life so far, and it was quite a wild ride.

The way that I experienced August 15th, 2021 was very different from how my loved ones experienced the day. I was clueless. This was about to be the best day of my life, and I had no idea. Everybody else did. I had suspected that maybe Michael would propose so I made sure to have my nails done and an outfit on that made me feel pretty. He quickly shut that thought down when I saw him. He even told me to go through his bag so that I knew he did not have a ring with him.

I got on a train early in the morning to head out to Montauk (aka. My favorite place ever). The train ride is about two hours. Michael was going to get on the train when it went through his town, so I wouldn’t be alone for long. My family had a hotel room in Montauk for the week and would be driving out later that night, but we wanted to take advantage of having the whole day to ourselves.

I teased Michael, although I definitely meant it, saying that he should have chosen that day to propose. We would be in my favorite place, and we both looked great. He was wearing a shirt that he had gotten the week before. I picked it out and thought he looked so handsome. He had been teasing me, saying he was going to propose for a while and I was really over getting my nails done regularly (they’re still recovering from months of acrylics).

Made it to Montauk

We made it to Montauk and took a taxi into the town. There was a street fair! I was so excited; I love street fairs. We walked around and looked at all of the beautiful artwork. Michael even bought me two of the most beautiful necklaces as an early birthday present. I was a little hurt that he had convinced me he wasn’t going to propose. Despite this, I was still having a really lovely afternoon. The people at the fair were so nice and it was so beautiful out. Just being in Montauk makes me smile, and having Michael’s hand in mine makes it that much better.

At this point we were starving. We went to a deli to get sausage egg and cheese sandwiches on a homemade croissant. Yum! Michael promised we’d go to the new ice cream place in town later so I waited to get something sweet. We sat on a bench and ate and by this point I was just happy to be with him. Looking back on it, he seemed distracted throughout the morning. He made some comments about his favorite places in Montauk that made me wonder when he had been there. I questioned him once or twice but he responded quickly and casually and that was enough for me. No one has ever described me as a very observant person, so I just let it go.

We made it to the beach, and it was hot! I picked up prosecco the night before so we sipped it in the sand. I love prosecco and I love sitting in the sand, so I couldn’t have been any happier. Michael, on the other hand, was very hot and doesn’t look getting sandy, so I really appreciated that he was sitting with me. I offered to change into our bathing suits and jump in the ocean, but he said no. That was weird. At times I thought maybe it was coming, but I had searched his bag on the train and I didn’t find a ring. I guess he’s just a better liar than I realized. And maybe I’m easily impressed because I can’t keep a secret to save my life.

We finished our prosecco and went for a walk down to our favorite spot where the beach turns into a state park and sand cliffs line the shoreline.

A hoodoo, also called a fairy chimney or earth pyramid, is a tall thin spire of usually soft rock, in this case sand. The word hoodoo comes from a voodoo religion which recognizes magical powers within natural features. We love the hoodoos. We spent my birthday in Montauk last year and we were so mystified by them when we found them. They’re really beautiful.

So we walked down the beach to see the hoodoos. I knew Michael was excited because he loves the hoodoos, and I stomped in the crash of the waves and looked for sea snail shells along the way. He has never understood why I like playing in the crash however he is very good at helping me find the best shells on the beach.

The Moment I Knew

We were past the crowded part of the beach and it was just us, walking, hand in hand. I am not sure how I didn’t notice earlier, but I almost walked all over a beautiful picnic with my sandy feet. I didn’t know what to think. Giggling and blushing I looked at Michael and said “I wonder who this is for?”. He laughed at me. I didn’t know what to do or say, and he took what felt like forever to start talking. He held my hands and started started his speech. I made him repeat it for me later because I was so flustered in the moment. It was perfect, I knew it would be. I have never felt more loved in my life. He had tears in his eyes asking me if I would marry him. 

He picked up a little box that had been hiding in the blanket and got down on one knee. I think I forgot to say yes. I thought my wet eyes and persistent smile said enough. He disagreed. He wanted to hear me say yes. I did, and he slid the most beautiful ring onto my finger. The same ring I have had on my Pinterest board since I was 15. I couldn’t wait to give him the biggest hug and kiss. As he got up and grabbed me I heard cheering from above.

Everyone was there. Our whole families standing at the top of the hoodoo cheering for us. All of the people that we love the most, there to celebrate me and my new fiancé.

-Kristen

Couple smiling at their beach picnic proposal

The Perfect Proposal by Michael

I’m writing my part of this post after Kristen, and I think that it’s great that everyone gets to hear about things through her eyes first. It really sounds like the perfect fairy tale day, exactly what I wanted for us. It definitely wasn’t easy to pull all of this together, and it didn’t go perfectly, but that’s okay. In fact, it made the day even more memorable and special 🙂 I’ll pull back the curtain a little bit for anyone who might be planning or expecting a proposal.

The morning of the proposal, I got up early (quite unusual for me), got dressed, and sat down with my sister to run through the plan for the day one more time. In a little while, I would board the train to Montauk with Kristen, and then just about everyone in both of our families would drive out to the park to surprise Kristen after the proposal. My sister had an absolutely crucial role, she was going to lead everyone to the secret spot on the hoodoos, and then she would split off from the group to set up the picnic. The day before, she and I had rehearsed all of this by actually making the two-hour trip and walking through every step. When it was time for me to go, I handed her the ring (she was going to hide it at the picnic) and asked her to wish me luck.

I felt confident as I waved goodbye to my mom at the train station. That was quickly cured when I promptly realized that I had boarded the wrong train to Montauk. The train that Kristen was on was delayed, and this one happened to pull into the station at the exact time it was scheduled to arrive. A tip for when you screw up while trying to put together the perfect day: stay positive, and just roll with it. I soon realized that I could hop off my train at the next station and just wait for Kristen’s train there—crisis averted!

I finally got on the right train and found Kristen. I have to take a moment to gush over my beautiful fiancée here; she looked absolutely radiant. She had the cutest outfit on, and she had done her nails with this white and gold design that I knew would perfectly match her ring. She was a little teary-eyed because her beloved dog Lacey had selfishly decided to die the day before (you should have seen the look on my face when I heard that news right before I planned to propose). Remember people, roll with it. I did my best to be there for her; it hurts so much to lose a pet.

I absolutely couldn’t wait to see how happy my surprise would make her. But, before I could do that, I had to break her heart, just a little bit. The whole past year, she had been getting her hopes up at every nice date we had (she couldn’t believe I hadn’t proposed during one of the beautiful sunsets in St. Augustine). I really wanted this to be a surprise, and I couldn’t let her suspect anything. So, I asked her to open up my bag to see that there was just a bottle of prosecco, some sunblock, and a beach towel (completely unrolled for good measure). “I don’t want you to be disappointed today, so I want you to see that I don’t have a ring.” I lied >:), but it was for a good cause.

While we walked through the town, I was secretly stalling to buy time for my sister to get everything ready. Around 11:30, I got a text from Kristen’s sister; she’d slept in, and her family had just left for the two-hour drive over. This was supposed to be done by 1pm. High tide was at 1:30pm, and my little picnic was set up on a precariously thin stretch of beach. I wanted her family to be there, but my picnic would get washed away if I waited too long!

Still not letting myself get caught up in worrying, I kept Kristen busy. We relaxed on the beach, drank our prosecco, and enjoyed being together. Around 1, I got a call from my sister where she said the secret phrase to signal that everything was ready “What time will you be home?” (you don’t want to know what “Do you need a ride home?” would have meant). We got up, I walked Kristen to our secret spot, and I asked her to marry me. None of the little hiccups mattered. Even when Kristen forgot to say yes.

So, if you’re planning a proposal or any similarly huge surprise, remember that they don’t know how it’s supposed to go. If you plan well, focus on what matters, and do your best with love in your heart, you’ll have the perfect time, just like we did.

-Michael

Montauk Beach Proposal
Montauk hoodoos picnic
Picnic beach proposal
Montauk Proposal
Perfect Beach Proposal
Montauk Engagement
Montauk Beach Proposal

What’s Next

It has been so exciting to start planning our wedding. We spent a full week touring countless wedding venues and finally found the perfect one. Click here to read about it, and click here to see all things wedding related.

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