I Planned My Own Wedding and Lived to Tell the Tale

In the end, there were 37 adults and two children.

Our wedding count includes the brides and the guys that owned our venue. They acted as our officiant and wedding coordinator, respectively, and stayed for the reception.

It was a gorgeous weekend, on a gorgeous piece of land that juts into the Chesapeake Bay. The Black Walnut Point Inn, a huge 150 year old B&B, and its property were ours for four days. Despite being in Maryland in June, our weather never topped 85 degrees.

In total, the wedding was a three-day affair. It started with a Friday dinner hosted by my parents at a lovely restaurant venue, followed by a casual night of board games and ridiculousness (complete with cow print table cloths, baby slideshows, and open bar).

The day of the wedding was an all-day, come-and-go-as-you-please pool party with lawn games and lunch prior to the 4:30 pm ceremony. After the ceremony there was a cocktail hour where guests could take informal pictures with silly props while the family stood for the photographer. Then, toasts, dinner (this time hosted by her parents), an amazing sunset, dancing, and a bonfire with s’mores. On the last morning, there was a family-only brunch.

The guests were happy, the schedule worked out, and the vendors did what they were supposed to do. Our parents and best friends were incredibly helpful and seemed happy to pitch in on site. We had a successful signature cocktail, awesome cake, beautiful flowers, and great food.

Best of all, we did it for less than $15K total, including parent contributions.

In order to make budget, we skipped professional music and got an inexpensive photographer. The photographer ended up being great but could only stay for about three hours. And, if my music stylings were not quite as awesome as I had anticipated, I could be proud that I managed to pull off three days’ worth of damn good, hand-picked, and uninterrupted music with no repeats that essentially matched each part of the occasion.

It was the wedding of our dreams but getting there was sort of a nightmare.

The reason that I use the word nightmare is because I had all but demanded that we take the easiest and cheapest routes possible for the wedding. My goal for the whole affair was to be chill about it. After all, it was supposed to be just one great day in the grand scheme of our lives.

The problem is that that never happens. In retrospect, I was being incredibly naïve.

So, every stressful moment felt like a deviation from my original purpose. Every thing that cost money was too expensive. Every moment that I spent planning felt like a waste of time.

Honestly, we probably couldn’t have done better. The things that went wrong along the way were all fairly typical. We had a few early arguments with family over the guest list, spent more money than we wanted, and became exhausted by the planning process. Caroline’s nerves got to her, I ended up not liking carefully-chosen dress, and we had to suffer an ill-mannered guest that we don’t really speak to anymore. Isn’t that everyone’s wedding?

The problem is that I believed that I could create the best day ever without breaking a sweat.

For us, one day turned into three, plus a day of onsite prep, and months of pre-planning. The ease with which I thought that I, a former meeting planner, could manage a 40-person event was completely blown away when we started telling people that having a small guest list would allow us to make things more special for everyone. It turns out that, once you go down the ‘special’ route, all other routes are lost to you.

For us, ‘special’ meant that all guests could enjoy an entire weekend away. They were invited to a faux rehearsal dinner (we didn’t have a wedding party), game night, day of play, ceremony, and reception. We told the guests that basically everything was optional, however. We wanted them to feel like they were on vacation and did everything to make it so.

‘Special’ was a surprise guest book that we designed ourselves which included a full page for everyone in attendance that had a picture of the person/couple and anecdotes about them and their relationships with us. Some of our guests didn’t know each other very well and, since we had so few people and were asking them to hang out for an extended period of time, we reasoned that this would help grease the wheels. (It did.)

‘Special’ was also a gift bag in each person’s room with a smaller version of the book and other niceties like a cute itinerary, sunscreen, mints, and tissues. And, ‘special’ included a parental gift presentation, marking tables at both dinners with pictures of things that are important to us instead of using numbers, giving everyone sparklers and mason jar mugs, setting up a photo booth with costumes, and more.

All of these things made sense at the time and were well-appreciated by our guests. The problem is that, once you start planning a ‘special’ event for 40, you realize that the amount of work is essentially the same for 40 as for 140.

The size of your wedding will make more of a difference in the pricing than in the planning.

This would have basically been okay if we had decided to ask for or hire planning help. But, we didn’t. Every concept, every errand, every piece of printed material was executed by one of the two of us until we got onsite. Even then, we did a huge amount of work and basically all of the event management. Though, to his credit, the B&B owner/wedding coordinator did try to take an active role. I just had trouble letting him because I hadn’t planned for him to help.

I think that the real mistake that we made was keeping it all in our heads. And, by that I mean “my head.” Caroline was in charge of several things and did a fabulous job but I basically micromanaged all of her work. (Sorry, sweetheart…) Right or wrong, I was the keeper of the big picture. We tried to plan everything out in advance but it’s just wasn’t possible. The tiniest things were actually the items that drove me nuts.

Case in point: I left the party about two hours before the ceremony to go get ready. I was in the shower, taking my first deep breath in hours, when I realized that I had forgotten to tell my sister-in-law, Valerie, where she could find the iPod and speakers for the ceremony. Then, I remembered that none of us had good cell service. I put on shorts and a t-shirt and hustled down to the wedding site.

When I got there, I found the iPod and was on my way to give it to Valerie when I got stopped by the caterer. I had sent the catering office the recipe for our signature cocktail but now it was nowhere to be found. They brought all the right ingredients but didn’t give the recipe to the bartender. Luckily for me, as I pulled out my phone to try to find the email, my brother Matt walked up to tell me he was on it.

My brother ordered me back to my cabin on the spot and I still have no idea what chain of people had to freak out for him to be able to deal with the issue. He certainly didn’t have the recipe in advance. Either way, that little diversion from my room cost me nearly a half hour and added quite a bit of stress as I was getting ready.

In the end, I wouldn’t change a thing about my wedding. It was awesome.

The thing that I would change is…me.

I wish that I would have been willing to spend a bit more money, had never procrastinated about the prep, and that I had been less anal retentive about creating a perfect weekend. I wish that I had made sure that I would enjoy the entire weekend more instead of only enjoying the end of each day (when the tasks were done and the drinking started). I wish that I had asked for more help.

So, if you were going to attempt the same wedding, I would tell you to get a planner and a band. I would tell you that, if you are doing all the work and incurring the lion’s share of expense, you should never compromise with anyone besides your partner. Skip inviting anyone that you don’t want to, even if it hurts their feelings and pisses other people off.  Think about the details without letting them consume you. Make sure that you carve out a space for yourself and take the time to enjoy it. And, finally, don’t take it too seriously.

Your wedding can easily be derailed by weather, guests, and any number of other small catastrophes. Your wedding experience can only be derailed by you.



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