My wedding (and how to plan a great one)
My wedding was fantastic. Yours can be too.
I recently got married to Sarah Winsberg. To kick off the marriage, we had a wedding. The wedding was fantastic, and even better than I could have hoped.
We had pretty strong opinions about how to plan our wedding (and what the theory of the wedding even is). While you shouldn’t copy everything we have done, there’s a lot we’re proud of.
Here are some great choices we made. Learn from us! (And later on, some things we got wrong. Learn from that too)
21 tips for a great wedding:
Food trucks! They solve so many problems.
Food trucks imply picnic-style seating. No worries about seating charts.
Food trucks make food on demand. No worries about nagging people about what they will order months ahead of time.
Food trucks can make more food if necessary. No need to worry about exactly who, or how many people, are coming.
Waiting in line for food trucks forces people to meet each other.
Food truck food comes with utensils. No need to clean dirty dishes or napkins: plastic forks and paper towels here.
Food trucks are fun! And give a nice picnic vibe
Food trucks are even (relatively) cheap
Understand this: the point of a wedding is to bring your people together and get them to understand why you should be married.
Once you have that orientation, a lot of decisions become easier to make.
This philosophy helps explain many of the other moves we made, like….
Your wedding can be a week-long party where you show off your hometown.
I'm so proud of this.
For years, I had told Sarah about my dream wedding: a week-long stay in a set of cabins in the woods, by a lake. People would spend the week playing games, toasting marshmallows, swimming in the lake, get drunk, falling in love, and all the best parts of summer camp. As we started to think through the practical steps to make this happen, this got steadily downgraded to a bachelor party, to a two-day affair, to rented airbnb weekend, to nothing.
But we did something almost as good instead: we had an optional extra week of wedding festivities tacked on. Here's how it went:
The wedding was on a Sunday. The henna party on a Friday.
Many people started trickling in on Wednesday.
That gave time for an impromptu bachelor party, bachlorette party, and tour of Rochester.
(Bowling alleys are great places for this kind of thing, by the way. They scale to handle an arbitrary, unknown number of partygoers. Bowling is a good balance of doing something with your hands and hanging with people. There's generally food. And there are arcade games nearby to entertain people who want to do something else.)
On the day after the wedding, Sarah's parents threw a wonderful long breakfast/brunch for everyone.
Ahead of time, we asked people to stay up to an extra five days after.
We created a group chat for everyone left, and showed of Rochester. We walked through the South Wedge. We ate at diners and chocolatiers. We had takeout. We threw a murder mystery party and a games day. We checked out the Museum of Play and toured cafes.
After all, if you've summoned some of your favorite people in the world together, why not make sure to enjoy it longer than one or two nights?
Pro tip: make an informal list of which guests are single and on the market. Find a way to get that list visible to each of them in turn. Grease the wheels a bit to help some magic happen. :-)
Community housing can be a key part of the experience.
Sarah and I didn't have a bridal suite. We got a giant airbnb, and invited some guests to stay with us in rooms there. We helped other groups of friends get airbnbs nearby. We had a little pop-up village for a week.
This was awesome! We had a "home base" where people could hang out in throughout the week. We always had people to chat with. We could observe our friends from very different places in life, become fast friends over the course of several days.
Honestly, it was heaven.
We got married outside, at a nature center
Indoors means the sound will echo off the walls, probably making conversation impossible if you also want music
Indoors is claustrophobic, cramped, loud.
Outdoors means that people can take long walks and get to know each other
Trees and grass and the outdoors are beautiful
The building that housed the nature center made amenities (bathrooms, kitchen) easy
They even let us have a bonfire!
That reminds me: yes, you need a tent. Yes, you probably won't need it. Yes, it will probably cost more than the actual venue. That's the tax you pay for being outdoors.
We invested in great music
Sarah's one desire was klezmer music and a klezmer dance leader. So we got both.
Again, music sounds great when the acoustics of indoors are no longer a factor.
A dance leader makes sure to draw people in so everyone is having a good time. Thank you Sarah Myerson!
Swords! (Invest in people getting to know each other, part 1)
I bought a ton of foam swords and scattered them around the grounds. This let people pick them up and have sword fights with each other. A great distraction for children of all ages
Secret Missions! (investing in introductions, part 2)
That wasn't enough. We also set up two boxes full of slips of paper.
In one box were the names of people at the wedding. The idea was that each attendee would randomly be matched with another person they had to find. This is harder than you might think: imagine reading "Alex Lo" on a slip of paper. How would you find him in a crowd? You'd have to ask strangers who he was, what he looked like, and so on.
But it gets better. In the other box, we had a list of secret missions to do with your randomly-selected partner. Everything from "share your favorite memory of Sahar (or Sarah)" to "start a pushup contest; get at least 3 others to join", or "walk like a certain animal. Get your partner to guess what animal you are".
One of my favorite memories of that day is watching Danila creep up on baby Linus, flapping his suit coat and arching his arm like the ears and trunk of an elephant.
The point of getting married is to help the world understand the relationship that you already have.
The night before we got married, Sarah and I stayed up late and talked about what marriage even means, to us. What does it mean?
Sarah, bless her, had the answer. Marriage is a way of helping other people understand the relationship we have.
To crudely paraphrase her, I think of it kind of like implementing an interface or an API. We’re telling the world that they can use a shorthand way to understand us and how to interact with us. There’s a certain number of actions or assumptions people can take with us (invite to dinner, remember the spouse’s name, understand that we’re a social unit) and get a predictable range of reactions to them. And, similarly, we get social permission to do things more easily (e.g. bring each other to work events, reference each other in conversation).
Importantly, just as you refactor code over and over behind a stable API, so too can we change our relationship to each other in the backend.
Emailed (or texted) invitations are fine.
Have a simple, relaxing, honeymoon
After all that effort, we didn't want the sort of honeymoon that involved long flights, mucking around with currency and passports and phone plans or languages. We wanted something easy, rejuvenating, and of special significance.
We chose Canada!
We went to the Thousand Islands (site of an early flirtation) and played a lot of board games (one specifically, Frosthaven) and kayaked. Then went to Stratford, Ontario (inspiration for Slings and Arrows, an early favorite TV show for our budding pre-romance) and saw the best Shakespeare I've ever seen in my life.
Dress amazing, not formal
I didn't want to be sweating and boring and stuffy in a suit. But I also didn't want to wear everyday normal clothes. What to do?
The answer: art. I wore arty clothes.
Sarah wanted a dress that was clearly a wedding dress. But I lobbied her not to go the "traditional" white. White wedding dresses were cemented by queen Victoria of England -- why would we want a dress that was all about emphasizing virginity? (And plus, as soon as you call it a "wedding" dress the price goes up by 1-2 orders of magnitude).
So we got a beautiful black and white dress from Saks for roughly a tenth of the cost of a mediocre wedding dress: it was white enough to be recognizably a bridal dress, but also looked fantastic on her, is reusable, was clearly a good idea
Wedding rings don't need to be stressful boring expensive and useless
Think of the symbolism of losing your wedding ring. Or the low-grade worry about caring for another expensive item on your person at all times. Or the annoyance of taking it off to go rock climbing all the time. What if I told you there was a better way?
Don't spend thousands of dollars on boring gold. Don't waste money on rocks (jews don't use them for wedding rings anyway!). We spent $3 each on jet black hematite rings from a nerdy store in Rochester. They looked great, and broke a few days later. Whatever, I can just buy more.
Redirect parent energy
There's an understandable amount of energy your parents will want to put into your wedding. Both of the heartwarming useful kind, and the other kind. You can't fight it head on. But you can harness it.
We handed off the henna party (think of it as a persian pre-wedding replacement for a rehearsal dinner) to the parents. They invited their must-have friends, they set up the venue, the food, etc. And they got to bond over doing it together!
We got a whole extra party out of it, and they got to have a fancier party that was more to their taste. I got to show off the persian side of my life, and we got an extra venue to fit in speeches and culturally significant (in this case, iranian and israeli) music. Win-win.
Get married in the early afternoon
Late enough that you can sleep in and prep, early enough that there's plenty of sun. Start around 2ish or 3ish, end around 11ish.
Have an afterparty venue picked out: probably your communal airbnb!
Replace vows with stories
Vows are what you pledge to each other. But your wedding isn't about the two of you, exactly. By the day of the wedding, you're already bonded, you already presumably have quietly talked over your expectations for what being married means.
Remember, the point of a wedding is to get your people to understand why you're getting married. So, instead of vows, tell that story. Introduce your new spouse to your friends and family. There's an old saying: "there's me, there's you, and there's our relationship". Introduce your relationship to your friends and family. Now is the time.
Children are great! Extra friends are great!
We were warned to disallow children. At first, we took this advice and asked people not to bring them. Later, we realized our mistake and changed our mind. I wish we had said children were encouraged from the beginning: a few key family members couldn't come because they made other plans.
Here's why children are fine, even great: if you're outdoors, and have food trucks, then marginal space is no longer a real issue. Let children come. Let them run around in the woods. The marginal cost of an extra food truck item is likely ~15 dollars a head, since you've eliminated seating and waiter labor costs. Feel free to spontaneously invite people to the wedding. It's fun!
Paradoxically: treat +1s with care
I have a lot of friends. If it were truly up to me, I would have invited around 400 people to the wedding, easily. So Sarah and I made a rule of thumb: if, in our years of dating, she hadn't met a friend of mine, I probably shouldn't invite them to the wedding. It was a wise rule.
Relatedly, we were a little worried about people bringing their spouses and +1s. Each +1 meant one less friend I could invite. (Especially before we realized that food trucks made size less of a constraint). So we came up with a similar rule for +1s: if we hadn't actually met the proposed additional guest yet, then they were sadly not invited. It seems to have worked!
And it had the unexpected effect of really nudging people to make friends at the wedding. While many of our friends are partnered, the lack of that partner meant that they couldn't socially "turtle up" as a twosome. That meant they were obliged to go make some new friends. This worked well.
Speeches are actually good -- but space them out
Just like we took bad advice to initially disallow children, we took bad advice to tamp down on speeches. Mistake!
We did get some speeches, and they were a highlight of the day. We handpicked friends and family, gave them a month to prepare, and spaced them out, two at a time, with an hour or two between each.
It went great! They were passionate, funny, and the people who weren't into listening to them could wander off and play with swords or explore the woods or whatever. Free range weddings make everything better.
Yes, drunken impromptu speeches at weddings are a trope. But for us, the speeches were amazing. They captivated the majority of the audience. (And again, that audience was self-selected). And even if Sarah and I were the only people paying attention: it was worth it.
If I could do it again, I would have had more of them. We certainly had the time for them. And it was a special moment.
Have a special moment with everyone with this one weird trick.
Weddings are weird. You have so many people there. You can't spend quality time with all of them. Someone that, in different circumstances, you'd happily spend a whole day with in deep conversation might only get a handshake and a selfie with you in a "normal" wedding. So how do we get that special moment of connection with everyone? Thankfully, our rabbi paved the way.
At some point during the ceremony, she told us to look around and remember the people around us (and they were around us -- part of the conceit is that you're surrounded by your people, not performing on a stage). I took it a half step further. I looked everyone there in the eye, one at a time, for a heartbeat or three, before moving on. It might have taken three minutes. It felt like half an hour. And it felt so good and wholesome. Try it.
Don't sweat the details. Many times, we told people, "if someone asks us what color napkins we want, then we are doing something horribly wrong".
First, the point of a wedding (see below) is not to show off your color coordination or fashion sense. Have fun. Second: if you want to make sure details like that are happening, get a wedding planner, set appropriate expectations, and let them handle it.
Example: we didn't even bother planning a bachlorette party. But our guests did gather spontaneously the night before the wedding, at that bowling alley. My sisters brought sassy bachlorette party themed items. We handed them out, it was a blast, and if you ask nicely I can show you some video of tipsy Sarah being adorable.
Things will be great. Don't worry. Enjoy yourself.
Bonus: listen to tradition. Have your wedding on a Sunday.
We chose our date of wedding like so: we wanted it in the summer, while Sarah wasn't teaching. A more traditional uncle ruled out many weekends because they were traditional days of mourning. Our rabbi said they she wouldn't officiate on Shabbat -- that weddings don't happen on Saturday or Friday nights. So, mostly by process of elimination, we chose Sunday late July. And it's a great thing we did.
The day before the wedding, we were going to go hiking with friends at a state park. We'd find some natural water, and immerse ourselves in it ritualistically as people do before weddings. Unfortunately, that Saturday, the day before the wedding, was a downpour. Not just a lot of rain -- enough to ground flights and cause some friends to miss the wedding entirely because their planes refused to land. Enough that, had we the wedding that day, a tent would not have been enough to save it. It would have been ruined.
But, luckily, the day after was perfect. Sunny. The ground was not even wet. Perfect. And having the wedding on a Sunday afternoon made it clear to people that we hoped and expected they'd stay longer than just the weekend.
We also got some stuff wrong. Here's what we learned:
Plan earlier, and there's no need to get overwhelmed.
We had heard, roughly, that you need to book a venue and send invitations about a year ahead of time. We started more or less on time following that advice, but got overwhelmed and punted.
What we really needed was to do lock down a few key things: venue, rabbi, planner.
Then we needed to actually invite people. (We did a bad job of this). We procrastinated a ton on this. Oops!
We spent much more time worrying and stressing about these than actually doing them. Don’t be like us.
Use a CRM. Avoid WithJoy.
We started with Airtable, but I wish we had started with a "wedding CRM". But don't use withJoy
Their tagging system is bad
They can't use filters! (This is a big deal)
Their software is buggy
They can't do basic bayesian searching on guests
The UX to change or view details about guests is annoying
I have heard good things about Zola?
You need a day-of captain
You need someone who is the majordomo of the schedule and logistics. They might corral people into their seats for the ceremony, or keep track of when is speech time.
Usually, I imagine it's the wedding planner. Relatedly, make sure you're on the same page as your wedding planner as to what they're supposed to be doing
Not having a day-of captain wasn't terrible, but it did mean we were hours behind schedule and things were generally confused.
Luckily, our klezmer dance leader stepped up after the ceremony, so that really helped. Thank you Sarah Meyerson!
You need an escape route
I don't remember what dessert we had. We didn't eat any. Ditto drinks. There was a whole little area -- a little pavilion, with drinks and food and so on -- that we never touched. Every time we walked towards there, we were waylaid by a conversation or person.
We also felt a duty to dance for hours. We got a band and dance leader: would it be proper to leave and sit down or go walk in the woods while they were on? In retrospect, yes. We needed a friend or two to watch over us, take us by the arm, and help us get out of situations.
Remember to schedule time and energy for thank you notes
We still have not sent thank-you notes. If you were at the wedding and didn't get one yet -- sorry! It's, uh, been difficult to find a time when we're both free and both energized to do it together. Sorry! I guess the lesson here is: "plan some writing-thank-you-notes date nights?"
Remember: dating is the search for someone who doesn’t just tolerate the things people might find difficult about you — instead, they positively delight in them. You'll know you're with the right person when they know you so very well, and are enthusiastic about not just your greatness but your foibles.
Wedding planning is, among other things, the exercise you take to distract yourself from the enormity of the step you’re about to take. Don't get too distracted. Don't get too overwhelmed. At the end of the day, even if you throw a BYOB picnic and invite your friends, it'll go great.
PS — I love weddings! I think I’m a great guest: fun, good dancer, great at making friends with your friends. I’d love to go to more: please invite me to yours.
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