I have planned and executed four bachelor parties in four different cities over the last decade. All four were drastically different in their size, scope, and location. And each groom emerged having had the time of his life.
There are many tried-and-true formulas to throwing a good bachelor party. It is not rocket science, after all. But there are a few intangibles that can make a night, day, or weekend with your boys transcend both time and space. Here's what you need to know:
Phase 1: Planning
Start with the basics: where, who, when, and what.
As for the where: I'm partial to New Orleans, where my own bachelor party was held. It easily provides all the debauchery you can handle, accommodates large groups of dudes, offers a multitude of non-alcoholic activities, and allows you to walk around with drinks — you know, just in case. Remember, when picking a location, it is vital to consider the size of your group and what you want out of the event. Las Vegas is designed to accommodate large groups and is great if your whole group likes to gamble. Toronto, by contrast, has several hotels that explicitly ban bachelor parties.
Group size matters. I cannot stress this enough. Anything larger than 10 is a nightmare for logistics. It means three or more cars, too many hotel rooms, and serious difficulties getting restaurant reservations. The golden number is somewhere between six and nine. At any given time, someone is ready to rally and re-energize the group. Plus, the group will be more mobile and easier to track.
Next up: accommodations. Here's an easy rule. If you can't fit your whole group in one hotel room, rent a house. The most important part of the bachelor party is often keeping the group together. For all the craziness that these events entail, one of my favorite moments from my bachelor party was having everyone together, grilling and playing drinking games. That feeling of camaraderie, youth, and freedom is tough to maintain if you have three separate hotel rooms on three separate floors. At one of the parties I planned, for example, half our group quietly checked out of the hotel and did not show up for our last breakfast. With separate hotel rooms, you will lose track of people.
The groom has a responsibility to manage the basic content of his party, but not to micromanage it. In the end, it is not entirely about him. Your groomsmen and friends may be married or have kids: They really need a weekend out. Still, if you are not into gambling or strip clubs, tell your best man. He will understand and plan accordingly. Two of the four bachelor parties I planned involved zero nudity. These grooms ended up performing a series of ridiculous tasks instead, and we had an amazing time. It is important that the groom is comfortable and that everyone planning is on board with the ground rules.
Now, as the planning progresses, there will surely be a group email or a group text, ideally one that continues throughout the party itself. With six or more guys on any of these, this will quickly digress to a series of memes, practical jokes, and maybe explicit photos. That is, of course, if your friends are any fun. That is why it is vital to have someone in charge who can actually manage the planning, logistics, and finances, and not get lost in sending a series of Schwarzenegger videos.
Phase 2: Execution
The best laid plans of best men will probably be thwarted within hours of the bachelor party beginning. At my bachelor party, of the 10 or so events my best man had planned, we ended up doing only a few. The party was still a wild success. Once you are "on the ground" you have to bob, weave, ebb, and flow. Something will go wrong. Things will change. No one expects perfection.
The first night we were in New Orleans for my bachelor party, we were going to "take it easy." We grilled, played drinking games, and had two planned stops — a bowling alley and a video game bar. The plan was to relax after everyone's flights and get ready for a big night on Saturday. By the time we started bowling, around 8 p.m., half the group was drunk, and the other half was catching up. Once we moved to the video game bar, the nine of us immediately split up and started playing various games. One by one, we all began looking for a bathroom, and one by one we all discovered the dance club in the back of the bar, playing mid-90s hip-hop and dance music. There were probably shots taken. There may have been a dance battle. By 3 a.m., a few of us had landed at the casino, a few of us had gotten lost chasing some girls to another bar, and at least one of us was asleep on the porch unable to find the house key. By 9 a.m., someone was unfathomably going for a run. This is where your group text can actually be useful, or at least hilarious. We may not have known what was happening at the time, but having a written account the morning after was golden.
The next day we ended up on a voodoo tour. We were — as a collective — some combination of still drunk and hungover. As the voodoo priest performed a series of rituals in Louis Armstrong Park, we struggled in the sun, mesmerized by the drum beat. After the tour, we downed muffalettas, went home, and tried to sleep off the hangovers. We rallied. Dinner plans were changed, and we set out to the bars. I had no idea what was coming, and with only two cups of coffee in me, no idea how long I would last.
By 10 p.m., we were supposed to be well into our drinks, but we were only getting started. A good bachelor party should, nay, must contain an element of surprise. This is why the groom cannot micromanage the process. The mix of fear and excitement needs to be in the air. And as an added bonus, it prevents you from having to lie or hide details from your fiancée.
Walking out of our first bar, hurricanes in hand, I saw one of my friends grab a pile of napkins. Then I saw the brass band. It was on. Having done just about every extreme sport there is — swimming with great whites, bungee jumping, sky diving, and so on — I can say confidently that there is no rush quite like having a surprise second line (parade) thrown in your honor with all of your best friends and 150 strangers in tow. Nothing.
As the dark rum kicked in, and the brass band picked up, the call-and-response tunes echoed down through the French Quarter, and everyone from bachelorette parties to bellhops to folks stuck in the traffic we had caused began to dance along as we waived our white kerchiefs. It was hypnotic, joyful, and the best of surprises.
Phase 3: Aftermath
After drinking everything Bourbon Street had to offer and watching it close down; after hearing the most unexpected secrets from the most unexpected person in the group; after meeting an unnamed celebrity at an unnamed establishment; after winning the casino's money; after sunrise, beignets, and chicory coffee; after watching the French Quarter reopen, I should have slept. But by 9 a.m., someone else was unfathomably going for a run, and the house awoke. I went to brunch with the group that had turned in "early." Some hours later, I was "forced" to don a pirate outfit and we hit the streets again for gumbo, jazz, and more drinks. Then, finally, sleep got the better of me.
On the last morning, I awoke to some amazing updates to the group text. One of my friends had already compiled GoPro videos of the parade and the weekend as a whole, and another had discovered how to create memes of embarrassing photos. Weeks later we are still egging each other on. The group text is now my favorite "app."
After I packed my suitcase, I wiped away a few joyful tears, and headed downstairs for one last exchange of stories. For a group of friends, the story is what matters — how you live it, how you retell it, and how you share it. In the days of Facebook and Twitter, it's all too easy to spread every detail of your life with a 1,000 of your "friends" or the general public, but to me — and I expect those of us in our mid-thirties — there is something special about having a night, a weekend, a trip that you just had to be there for.
Having every one of my close friends in one place — at a time in my life where that so rarely happens — was priceless. Having every single person who was invited actually show up, commit to the party, and make every possible physical effort to make the weekend unforgettable made it something more than words can possibly do justice. So if you are lucky enough to be planning a bachelor party, or just attending one, put in the time and money. You will get it back in spades. And if you are being thrown a party, congratulations: You are in for the night of your life.