My Engagement & Proposal Story

Last November (2018) I shared with you that I was celebrating my ten year wedding anniversary and in that blog post I mentioned that I would (finally) be sharing my proposal story with you as well. With the holidays over and Valentine’s Day well on its way, we’re in the heart of what feels like “proposal season”. In this post, I’ll be sharing my proposal story, but also a list of tips for what might work for you (so you can create your own beautiful story).

I get asked about my proposal story a TON, especially once people realize where he proposed. It really does feel like a story straight out of a rom-com and I’m excited to share it with you, too…

Disclaimer: These photos are super old, we had a crappy camera and this was circa the release of the first iPhone! Instagram didn’t exist, most of our friends were’t even on Facebook yet. Hiring a photographer wasn’t a feasible option back then either, so try not to laugh too hard at the quality of these pics…or my bangs and eyeshadow.

My Proposal Story

My husband and I started dating in November 2007. Before we got together, I knew that he had an impending work trip to NYC in February of 2008 and made a joke that he should take me with him because he’d be there over my birthday, it was my favourite city and all that (true story). We weren’t dating when I made these comments…

Once we’d started dating, I’d tossed around the idea of actually joining him on his NYC trip. He’d be working during the day, but I knew the city well enough to get around on my own and then we could spend the evenings together. I had planned a girls trip to Toronto (to see the Spice Girls!) for a few days before the NYC dates and thought I could try and meet him there. Little did I know, the wheels were already turning in his head.

For Christmas, he and my parents got together and booked flights for me to do just that – fly from Toronto to meet him in NYC on my birthday and then return home together a few days later. He told me that he’d already made dinner reservations for us at The Rainbow Room at Rockefeller Centre, where afterwards we could go to The Top of The Rock to view the city lights. A spot in the city I had earlier mentioned was one of my favourites.

When I mentioned how excited I was about the extravagant plans my boyfriend had made for my birthday many made jokes about him proposing. “You’re an idiot if you don’t think he’s going to propose” is what I’d heard from a number of people. Keep in mind, though, that my birthday would mark our approximate three month dating anniversary. Of course I loved the idea of him proposing, but couldn’t imagine he’d do it this soon.

I don’t want to say that we got “really serious really fast” because it didn’t feel like that. We just clicked. We talked about what we wanted out of life, of marriage, having a family, our goals and dreams. It all felt really natural. They always say that when you know, you know, and I think we just knew…and my parents did, too. While I was away in Toronto, he went over to ask their permission.

Fast forward to my 24th birthday…I arrive in NYC and meet him at the hotel. We get dressed up and we head over to Rockefeller Centre for dinner. He seemed self-assured the entire time…no signs of nervousness.

We had a lovely dinner overlooking the city lights. His brother called and he said it was to “wish me a happy birthday” when really it was a “did you do it yet?” call.

After cake and the traditional birthday musts, we headed upstairs to The Top of The Rock Observation Deck. I still maintain that these are some of the best unimpeded views of New York City.

Here’s where the real rom-com moment begins…

To enter the observation deck, you must first go through a TSA-style security checkpoint. Now, I’m someone who has forgotten and lost items at these checkpoints in the past, so I was busy making sure I had all my belongings, not realizing that Van had hit a snag…and had to show the security officer that he had a ring with him. Crisis averted!

It was one of those humid winter nights in early February. One of those nights where the fog rolls in off the water and just hangs in the air, softening and muting the city lights. The slight chill makes you snuggle a little closer while enjoying the captivating and romantic views. This also made for fewer people on the observation deck.

We found a spot with few bystanders and then it happened. He turned and looked at me with his arms around me, said some very lovely things, and then reached into his coat and presented a little box, which he then opened. My immediate reaction was colourful to say the least.

I believe my words were “holy f*&%, is that an engagement ring?” to which he replied with a laugh, “Yes it is. Will you marry me?” I answered with “Yes, yes, oh my gawd, yes!”

I remember taking this photo when we got back to street level and asked a couple of older tourists to snap it for us saying “Can you take a photo of us? We just got engaged!!!” They were elated for us, sharing in our joy and sent us off with their well-wishes for our future together.

Some people wondered why he didn’t get down on one knee, but to be honest, it didn’t suit the moment – our moment. We were closer to one another and it kept the whole thing much more private and intimate between the two of us. Putting on a show just isn’t Van’s style and I’m glad he didn’t see the need to put on a show for the tourists. Our story is quiet and romantic, private but spectacular.

We returned to our hotel to change into jeans and then headed out to celebrate and explore the city. This was and still is, very much us


Proposal Tips to Help You Pop the Question!

Proposing to your significant other is no small moment in your relationship, and should be done with a few things in mind: timing, style, and even your partner’s personality type! I’ve compiled a list of things to consider when proposing. Now that you’ve heard my proposal story, these tips might help you consider what works best for you!

Timing Is Everything

Just like the other pivotal moments you have shared together, timing is everything when it comes time to pop the question. When you know they’re the one, you know, but you should also make sure your partner is ready and on the same page. Many factors go into planning a wedding and a life together, including finances and personal lifestyle choices, so be sure to consult with your partner about the idea of marriage prior to asking the big question. This will keep stress levels low and excitement high when it comes time to ask them to spend the rest of your lives together.

Van and I talked about everything in the first months of our relationship and we continue to do so. I believe it’s part of what keeps our connection so strong – being on the same page!

The Right Ring & The Right Venue

Planning shouldn’t be rushed, so maybe set a date to give yourself a measurable time frame. This gives you time to review your budget, venue ideas, and find the engagement ring! Finding the perfect ring will take up a bulk of your preparation time, especially to find the one that represents you and your significant other and the love you share. Find inspiration on sites like Blue Nile, where customizable engagement rings are an option, to help create a unique and personal design perfect for the love of your life.

Give yourself plenty of time prior to your prospective proposal date to get the ring sized and ready for the big day, and accommodate for any surprise ring reveals. Letting venues know ahead of time is also helpful and can give them the opportunity to prepare if needed.

Obviously Van had the trip to NYC earmarked in his mind as a possibility. He also knew my birthday could be a great opportunity to make a special night even more special. I didn’t realize this, but he’d bought the ring only 6 weeks after we’d started dating and wanted to make sure it was as close to the right size as possible (without giving away the surprise) because he knew I’d want to wear it right away.

All About Style: Trendy vs. Traditional Proposals

Trendy engagements tend to be more over the top or unique than your average proposal, with most ending with a memorable story to tell friends and family for years to come. Many are opting for engagements planned around a get-away or travel, which provides a beautiful and unique backdrop for popping the question! Others may make the engagement extravagant, but still tailored to their partner in every way, while making it a public event for all bystanders to be a part of. These engagements are special and full of energy and people to celebrate in the excitement afterwards. There are so many trendy options to make your proposal stand out from the rest. Check out this list of 2018 trendiest proposals ideas to spark some inspiration and ideas!

A more traditional proposal is often done on one knee amongst your closest friends and family. Or, a more intimate moment for just you and your partner to revel in. With the holidays in full swing, it may be the perfect time to pop the question at your family get-together. Be sure to ask for their permission prior to asking for significant others hand in marriage, and then get them involved with the planning! They can help to make the moment more personable to both you and your partner. Or, find a beautiful holiday backdrop decorated with stringed lights for a romantic and intimate proposal. Having it just be you two can take some pressure off the moment and make it just about the two of you in this exciting moment.

I can’t stress enough how much you will remember this moment for the rest of your life, so you want to get it right. Don’t let someone talk you out of a romantic gesture that you know your partner will love. Have a trip booked to Paris or a snowy mountain retreat? If you know how you want to propose, then don’t let a potential logistical issue stand in your way.

Personality Playing A Role

Sometimes your partner’s personality can dictate the proposal as well. If you partner is more introverted, a widely extravagant and public engagement might not be for them. Or if they have a more extroverted personality, a shareable experience with friends and even strangers may be their preferred proposal. No one knows your partner like you, so consider this when planning. This plays a huge role in the style of proposal, and can make all the difference on the big day. Having your partner feel uncomfortable, pressured, or under/overwhelmed can take away from your big gesture, so knowing what they like and don’t like can help to alleviate this from happening. Ask friends and family for some ideas as well, and maybe steal a look at their Pinterest or Instagram for ideas of how to make it what they have always dreamed of!

Online resources like these (and most social media platforms) didn’t exist when I got engaged, so use them to your advantage. There are so many ways (big or small) to make this moment an incredibly special memory. I hope this helps you to plan the perfect proposal and that my own story inspired you as well!

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Carlee Krtolica
Carlee Krtolica

Editor-In-Chief

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