From Proposal to ‘I Do’: My Wedding Timeline

When I first got engaged in 2019, I knew I wanted to track the wedding planning journey. From cost considerations to a vendor search and all the planning in between, there’s a lot of work that can go into two people getting married. It took 2 years for this post to go from draft to publish. Of course, the ending looks nothing like how I thought it would when I first started out, or even halfway through my engagement. Here’s my wedding timeline.

January 2019

Ian proposed at an onsen in Hokkaido, Japan during a two-week-long vacation. It was a complete surprise and an amazing experience. While the majority of the month was just enjoying the fact that we had committed to becoming husband and wife, we did discuss some high-level wedding details:

  • Draft up an initial guest list. First pass: 100-110 people
  • Decide on our top-choice wedding location: Manhattan 💸
  • Discuss initial budget: $10K each 😱

For a location, we wanted a place that was special to us, as convenient for our guests as possible, and also had interesting things to do for guests aside from watching us get married. NYC won out. The prospect of getting married in NYC was so exciting, we agreed that we could spend a little more. We wanted to make sure that we could pay for the entire thing without using debt or our parents.

I tried to find a cute engagement photo from the trip, but the majority of the pictures I took were of ramen so this felt more appropriate.

February 2019

After receiving some initial quotes from vendors in the NYC, we realized we were wayyyy over our heads. Did you know having a wedding at the New York Public Library can set you back $60K+?!?

I reached out to Twitter & Reddit for some help and got one solid piece of advice – to go the restaurant route. Once I started reaching out to restaurants with enough space, the numbers began sounding way more reasonable. However, none of them came in within our $20K total budget limit. Food, drink, and venue booking was okay, but once you started factoring flowers, a DJ, and taxes & fees, everything was still over budget.

We kept reaching out to potential venues in NYC but also started thinking about what a wedding outside of New York would look like. We’re more flexible on our location than our guest list. With the size of Ian’s family, we’re basically in a 100+ or <15 guest list situation.

March 2019

After realizing that New York would be extremely expensive no matter what option we took, Ian and I seriously considered having a backyard wedding in West Virginia, at his parents house. We scoped out the costs of getting a shuttle service, chair and table rental, and tent setup. It wouldn’t have been cheap, but we would have had significantly more freedom to prepare and celebrate, with the benefit of an intimate setting.

Unfortunately, Ian’s parents shot our proposal down when we presented it.

April 2019

With West Virginia out of the running, New York and the surrounding area was still our top choice, closely followed by Northern Virginia, which is where I grew up. Around this time, we also got closer to finalizing a guest list count, which was now at ~150 people. A lot of venues in New York cannot fit that many people.

In a stroke of good fortune, a friend from college introduced me to a couple that was getting married in a few short weeks but wanted a choreographed first dance. I offered to choreograph a simple waltz routine for them. Not only did they pay me $200 for the service (a steal for them and a fun experience for me), but the bride shared with me research from her sister’s wedding planning a few years prior.

May 2019

Armed with the research already done for A HUNDRED NYC-area venues in the last year, I quickly realized that our initial expectations around our wedding budget were highly unrealistic. After weeks of fretting, Ian and I decided that our wedding wasn’t going to be an event where we needed to pinch pennies.

New Budget: $10K each $30K each

With a better understanding of how much things were actually going to cost with 150 guests, I re-entered the venue search and scheduled a few walk-throughs. The first place I went to ended up being my favorite: it had the lowest price per head for catered food with an open bar and didn’t sacrifice city views.

This doesn’t look like much, but getting a skyline view in Manhattan was amazing to me. Plus, at night, the lights made the city sparkle.

June 2019

Since we had found a place that we liked, there was no reason to not place a deposit for the date we wanted. Paying the deposit (~$4K) was a weight lifted from my chest; with the venue, food, and drink all taken care of, I only needed to concern myself with was the fun stuff! That meant dessert, a photo booth, music, and decoration. Plus, by selecting a venue 16 months before the actual wedding, we were way ahead of schedule.

An important note: throughout this entire process, it was important for me to be able to pay for this entire wedding without any debt. By recently deciding to not buy a house (yet), I had cash on hand for this deposit. Most of the money I had started putting aside for a downpayment in 2018 was immediately made available for wedding expenses (~15K).

July & August 2019

Very little happened these months! Ian and I sampled the caterer to get a sense of the style, but no decisions on food needed to be made until 2020. I kept on saving.

We confirmed our officiant (a close friend) as well as the members of the wedding party.

In July, I went to Disney World with some bridesmaids (although they didn’t know they were going to be bridesmaids until a few months later).

September 2019

With the goal of getting save the dates out early, we started working on our wedding website. Our side hustle involves managing a website, so Ian has lots of experience and we wanted our site to be extremely thorough. Also, recognizing that October in New York City is an incredibly expensive time to visit, we felt it was important to give our loved ones as much time as possible to figure out their housing.

October 2019

1 year until the wedding! There wasn’t a ton of progress here, although we started to discuss color scheme, specific elements that were important to us, and, most importantly, finalizing the guest list.

On a random weekend afternoon walking through Washington Square Park, I came across a lovely Jazz trio playing. Their cover of Over The Rainbow made me feel things, so I messaged them on the spot to see if they’d be available to play at our reception. It was something utterly unexpected, but Ian and I really enjoy Jazz, so it felt appropriate to get live music for the wedding.

November 2019

Lots of action here! I set December appointments to try on wedding dresses.

A friend of Ian’s was transitioning into the wedding planning business, and we set up a call with her to be her potential first clients. After some back and forth, we decided to hire her as a day-of coordinator, as I had a lot of things already taken care of from a planning perspective.

We made progress on the wedding website, finalizing everything but our photos page, which ended up to be the most time consuming portion of the site as Ian is an amateur photographer with many photos of us over the years to choose from.

December 2019

The wedding website, which also functioned as a save the date, was shared out (finally) with friends and family. We also locked in a photographer, and started planning details for our summer combined Hen/Stag.

For dress shopping, I made a weekend of it in NYC just before the holidays and invited my wedding party to join in on the experience. It was a 2-day experience filled with morning try-ons, and then massive food consumption the rest of the day. I went to Kleinfeld’s for the experience, and then Anthropologie because their price ranges were far more in line with what I wanted. I ended up really liking a Kleinfeld’s dress, and didn’t pick out a dress that weekend, but it was my first real bridal experience with friends, so that itself was a blast.

January 2020

After the holidays and much deliberation, I revisited Kleinfeld’s after work one day to re-try a dress a had really liked in my first appointment, as well as some similar styles. In the end, I did make a selection, although at $5K, it was way more than I had originally planned to spend.

Ian and I had a proper session of going over the wedding budget, where we discussed what we wanted out the event, along with how the ever-growing invite list affected our total costs.

When it comes to weddings, I’ve come across two major groups of thought; either keep the costs as low as possible, as it’s just one night of extravagance, or, do everything you want to do because it’s one big night of extravagance that you (ideally) won’t get to have again. I started out agreeing with the former, but gradually moved over to the latter. There were the realities of having a large wedding in Manhattan; no matter how much we wanted to reduce the costs, we couldn’t do so without significantly changing the experience we wanted.

Ultimately, we re-worked our budget to be more reflective of realistic costs. Thanks to aggressive saving (and my high-paying job), I felt confident about being able to save up my share in cash, which was a minimum requirement for me. I don’t believe in starting a marriage with fresh debt if it can be helped.

New Budget: $30K each $50K each

February – April 2020

We locked in a DJ, which was the final big vendor missing on our checklist.

With Coronavirus looming over everyone, the only other progress made these few months was on finalizing the wedding invitations and collecting mailing addresses. Without understanding anything about how long the shutdown would last, we made an assumption that things would improve by October. In retrospect, we were laughably naive.

I left NYC late March after my company went fully remote. At home, I picked up a new hobby that I never would have had space for in a tiny Manhattan apartment: puzzles.

May & June 2020

After two months of working remotely and seeing the global situation just get worse, we realized that COVID wasn’t going anywhere. After a tearful conversation where I made peace with the fact that I just wasn’t going to have a conventional wedding, we worked with our venue to reschedule our October reception to July 2021.

The new plan? Still get married on our original October date in the city, but with a smaller group, and have a separate reception once it was safe to congregate.

We began notifying our guests of the change in dates, and also canceled our combined bachelor/bachelorette weekend. Our vendors were thankfully all flexible and considerate and handled the change with no resigned contracts or deposits needed.

July – September 2020

With the large reception successfully pushed back until next year, all we had to do now was plan a small wedding. Since we were now going to have a much smaller guest list, we could now reconsider a venue that had originally been our top choice, but was originally dismissed due to feasibility with many guests — Central Park.

Our new guest list consisted of 15 people: immediate family, the bridal party, and our officiant. With this small of a group, I could’ve marched up to a random tree or park bench and announced ‘Let’s get married here‘ and it would’ve been fine.

We spent this time booking hotels, restaurants and planning a packed weekend itinerary. I stocked up on wedding-related goodies like bridesmaids’ gifts and made arrangements for things like a pet-sitter during dinner the day of.

October 2020

It’s said that whatever can go wrong during a wedding will go wrong. A pandemic may have thrown things wildly off track early on, but that didn’t mean wedding planning went smoothly after that. Sure, there were plenty of last-minute hiccups the day of that we had to adjust for. Dealing with traffic due to a nearby protest, changing our ceremony location just before our start time, getting a group of people from Central Park to the West Village through Times Square — all of these things were ultimately surmountable, and it made our experience special.

Our October wedding in Central Park at Belvedere Castle was perfect, and all the stress, work, and tears leading up to the day made me appreciate it all the more.

Photo by Bethany Michaela Photography

This isn’t the end! We never came close to hitting the $100K budget we had set – costs leading up to the wedding day didn’t come close to the total budget, and we ultimately had to cancel our reception when our venue flaked. That story is for another day, though. I’ll be writing up a full NYC wedding cost breakdown in my next post!

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