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My Relationship Expectations Almost Ruined My Man's Proposal

Love & Relationships

For my 28th birthday, my boyfriend surprised me with a trip to Catalina Island.


We went parasailing, rock climbing, had a couple's massage, and drinks before heading back to our hotel, a cozy B&B-styled inn - very different from any hotel we had ever visited. It was absolutely perfect. I had been secretly hoping he would propose to me and my birthday felt like the perfect occasion for him to do so. After years of dating, and more recently my engagement questioning being following with a mere "soon" from him, I was anxious for him to pop the question.

I was more than ready to finally start planning happily ever after with the man of my dreams.

We talked about marriage often but until a ring was on my finger I felt as though it was merely that, just talk. I was becoming frustrated with simply being a "girlfriend" and couldn't understand why he hadn't yet asked me to marry him. Sure, finances weren't exactly perfect, but if we could make things work living together, we could also find a way to do so as a married couple.

By the time dinner came around, I simply could not sit still. Seated at a table with a gorgeous view of the outside, I imagined a band coming up and singing as he got down on one knee, or possibly the other diners applauding and taking pictures as he proposed. The possibilities of our dinner being "the moment", had me jittery with anticipation for what he would surely ask me. But, when dessert came and no proposal had happened, I desperately tried to disguise the look of utter disappointment on my face. "You ready to go?" he asked after we had both had a few bites of the ice cream and chocolate dessert the restaurant gifted me.

"Sure," was the only response I could muster.

When we got back to the hotel, I threw on sweats and a sweatshirt he had purchased for my birthday and laid across the bed. Scrolling aimlessly through my phone, I did anything to avoid facing him. I was hurt. In all fairness, the day had gone perfectly. He purchased me a few gifts that I loved on top of all of the fun things we did together, but I didn't get the one thing I truly wanted: an engagement ring.

Admittedly, I'm the type of person that always wants to be in control of things. Hell, if I go out, I always try to be the one who drives so I have control of when I leave - and that's one example of my need for control. I like things done a certain way so I always end up doing everything myself. When it comes to my relationship though, I felt powerless in not being able to decide when I got engaged. The lack of control was driving me insane.

When I finally realized nothing else was going to happen and I wouldn't receive the proposal of my dreams, I got underneath the covers and started dozing off to prevent my frustration from causing me to say something to him that I didn't mean. "Are you going to sleep?" he asked.

"I started dozing off," I admitted.

"Well, you can't go to sleep this early on your birthday, it isn't even 10 o'clock. Lets go for a walk or something, I'm not tired."

"Fine we can do that," I slipped on some sandals and sneaked a peak at him. Realizing he hadn't grabbed for anything out of his bag or changed out of his suit from dinner, I started to come to terms that it simply was not going to happen.

We walked aimlessly around the island talking and taking in the views. I mostly listened until we reached a spot by the rocks where the moon perfectly shone down on the water as the waves crashed against the rocks. "I probably could have bought you that bag you wanted, you know if we didn't do all this," he said.

I could hear the negative self-talk in the back of my head:Well, then you could have also bought a ring. I stopped myself from saying it aloud. "When we get back I really want to work on being a better boyfriend." Boyfriend? Not fiancé? Not husband? I stopped myself again. It took everything in my power not to blurt out, "Okay, so why didn't you propose?" I knew that he had worked hard on planning my birthday and that he had sacrificed a lot financially to ensure I had an amazing day so I bit my tongue with my disappointments.

"So you ready to head back?" he asked.

"Yea," was my only response.

"Oh yea I forgot I have one more gift for you."

The moonlight revealed a cunning smile on his face. It was in that moment that I knew he was about to propose. "I want to give you my heart, and my last name, and make you my wife."

He slowly got on one knee and revealed the ring that had been in his pocket the entire time. A meticulously placed light shone directly on the most gorgeous ring I had ever seen. "Ashley, will you marry me?" he asked.

"You tricked me! Yes, Yes, I love you," I cried as I became swept up into the hug he gave me.

The walk back was full of laughter as he revealed to me the joy he had watching me squirm knowing what he planned, the conversation he had on the phone with my parents the day before when he asked my dad for my hand in marriage, and how he wanted us to tell his mother about the engagement together in person.

After his proposal, I realized a few things.

If he proposed to me at the restaurant, it wouldn't have been the same. I would have been expecting it and who honestly wants to be able to pinpoint the exact time of their engagement?

I also realized the importance of allowing things to happen in their own timing. While I do like being in control as often as possible, some things are simply more beautiful when you allow them to just happen organically. Over the years I had imagined his proposal going a million different ways, but nothing was more beautiful to me than exactly how it happened: me wearing sweats, him dressed to the nines, and us overlooking the waves crashing down on the rocks.

I look forward to spending the rest of my life with my soon to be husband and take his proposal as a valuable lesson to learn to allow life to take its course. When you stop trying to dictate how everything in your life should go, some truly amazing things will happen along the way.

What was your proposal like? If you're still a single lady, what's your dream proposal like? Let us know in the comments below!

xoNecole is always looking for new voices and empowering stories to add to our platform. If you have an interesting story or personal essay that you'd love to share, we'd love to hear from you. Contact us at submissons@xonecole.com

Featured image by Getty Images

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