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Answer by Joel Lewenstein, officiated a wedding in 2015:
Last year I officiated the wedding of two good friends. It was an honor to be asked, and despite a fair amount of anxiety as the big day approached (I was more nervous than the couple), it was overall a deeply fun and rewarding experience. The best things I did to prepare were:
Attend weddings. This one is a bit out of your control, but try and watch ceremonies similar to the one you'll perform. Be critical about what works and what doesn't: length, structure, specific jokes, traditions, etc. Ideally you'd attend weddings with the couple you're officiating for, so you can get their specific feedback on ideas.
Start early. I began thinking (read: stressing) about the ceremony months before it happened. I collected lots of material (more on that next), then wrote and rewrote many drafts. I turned ideas over in my head and tried different angles on the ideas I wanted to convey. As with any piece of writing, the material evolves and improves significantly the more you work on it. This is especially true for a new type of oration that you've never done before.
Collect unique stories. This is by far the most important one—get a ton of material specific to the couple. Talk to them about how they met, what they like about each other, funny memories. Talk to their friends. Try to meet their families and get a sense for where they came from. I had never met the bride's family, so I flew to their home in Seattle and had a wonderful time getting to know her hometown and upbringing.
The key here is to get specific, humorous stories about your friends. The uncomfortable truth is that, unless you're a poet, it's hard to talk about the “meaning of love” in a way that resonates with 180 people. (If the couple wanted musings on the eternal power of love, they would have asked their rabbi to officiate.) As a friend of the couple, your wheelhouse is going to be describing them in an entertaining way: What makes your friends so special? What are their most distinctive qualities that you can gently tease? Did they meet in a particularly humorous way? Does he have an annoying habit that only she can tolerate, that you can gently tease him about?
Tactically, I chose to gather a lot of anecdotes then tried different themes to weave them together. I ended up talking about how opposites attract and telling three to four stories per person contrasting their different qualities. You should of course pick a theme that resonates with your couple, but a series of funny stories can really anchor a ceremony.
Talk to the couple. Ask them questions about their preferences: length of ceremony, seriousness, religion, specific traditions to incorporate, family members to recognize, etc. Beyond specifics, try to understand the mood and feeling they want: a serious and important tribute to timeless love, or a quirky and informal gathering of friends.
One big thing to ask them: How surprised do they want to be? Some couples want veto power on every line of the ceremony; others want to direct the broad strokes but hear the details for the first time at the ceremony. Regardless of their desire for surprise, you should make sure to ask about risqué jokes or references. Once I had a draft I was happy with, I picked out the jokes most likely to make the couple uncomfortable and got line-item approval.
Know your audience. This was the best piece of advice I was given: Remember who you're talking to here. For most weddings, it's a moment for the couple and their parents. Yes, there are friends and extended relatives there, but you're not playing to the whole crowd. It's tempting to try to impress your college friends with a winking reference to that one spring break trip from college. Don't.
Keep it short. This is more as a wedding guest than officiant, but the No. 1 ceremony sin is going on too long. Ask the couple how long of a ceremony they want and shoot for that, and when in doubt: Err short and cut your mediocre material.
Closely related: Have an editor. Have a trusted friend read the ceremony draft and give feedback. Bonus points if he or she is a good writer or professional wordsmith. The editor should primarily be looking out for structure, length, and timing: Did the transitions between sections make sense? Was anything redundant? Did a certain part drag or feel boring? If a section isn't working, cut it. If a joke is too hard to land, drop it. Do this a few times over, as you iterate on drafts.
Practice delivery. This is just general public speaking advice, but remember that the delivery is a huge part of the package. Once you have a near-final draft, practice the shit out of it. Get your comedic timing down. Perform for friends, and gauge their reactions. Talk twice as slowly as you think you need to.
One extra thing I did was try and simulate the nervousness I knew I'd feel. I'm not an experienced public speaker, so I knew that going from rehearsing by myself straight to the real deal in front of 150 guests was going to terrify me. So I took the interim step of rehearsing in front of my girlfriend's parents: They were a new audience (and my girlfriend's parents!) so it was slightly intimidating, so I was able to practice while nervous. That helped me ramp up the performance anxiety toward the real day.
Relax. You're the home team. For most weddings, everyone in attendance is a close friend of the couple, elated to be witnessing their marriage, and there to share in the celebration. They're not looking to critique your word choice, point out logical flaws, or jump on you for mistakes. So relax and enjoy the moment. If something doesn't go according to plan (and it never does), crack a joke and roll with it.
Enjoy! This is a huge amount of work, but I'm really happy that I did it.
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