How to Throw a Legendary Bachelor Party: A Best Man's Guide

I’m at W*’s bachelor party and sharing one of my all time favorite memories about a drunken night out in Montreal. W* and a few of the other boys at the party were involved with the story. I figured that since it meant so much to me, they must remember it too.

But when I finished telling the story, something weird happened. Everyone looked at me confused. No one else remembered it. I should have been embarrassed that this moment, which meant so much to me, was completely forgettable to everyone else, but actually, it was hysterical.

***

Bachelor parties call up images of endless rounds of shots, lap dances, and belligerence.

While there is a time and a place for that, if a bachelor party is defined by debauchery, you’re shortchanging the bachelor and all of the attendees of an event that could be unforgettable.

Over the past five years, I’ve thrown numerous bachelor parties for my boys (yes, I’m like the male version of “27 Dresses”). I’ve learned that a well done bachelor party is much more than just a group of guys getting drunk in honor of the groom.

Instead, it’s a small work of art that – when done well – will be remembered in vivid detail by the groom for the rest of his life.

What follows is a guide for the Best Man on how to throw an amazing bachelor party.

Implement the “Grown Ass Man” Rule

There should be one and only one rule that pervades a real man’s bachelor party, and that is the, “Grown Ass Man Rule.” Simply put, everyone should assume that he (and all the other boys) are Grown Ass Men. That means that each guy will take care of themselves, monitor their own behavior, figure out what to do if they get separated from the pack, and ask for help when they need it.

Not only is this respectful to all of the attendees, it also takes serious pressure off of you, the best man, by politely declaring that you will not be baby sitting anyone.

I explicitly state this rule a day or two ahead of time to help set clear boundaries and expectations for behavior.

Build the Party With the Bachelor in Mind

As you begin to organize the party, think of what would delight your bachelor. If he loves to play pool, make sure you hit up a pool hall. If he’s the quiet type, resist the temptation to turn him into a spectacle while you’re in public. If he has a soft spot for rare scotches, find the nearest scotch bar, and make a reservation.

Tailoring the party to the bachelor’s unique disposition and preferences is an easy way to make an emotional impact. If you’re feeling ambitious you can make it your goal to create a bachelor party that is even more fun for the bachelor than the wedding itself.

Ask the Bachelor Who He Wants There and Then Get as Many to Show up as Possible

Send out a survey to the list the bachelor gives you, asking which dates and locations work best. Schedule the party at the time and place that allows as many men as possible to attend. While choosing an exotic location and working from there is tempting, keep in mind that people are always more important than places. It’s easy to have fun in a shitty location with great people.

Get the Dad Involved

Bachelor parties are one of the few male coming-of-age rituals still observed. Because of that, you can create magic for both the bachelor and his father by getting the Dad involved.

In most cases, I wouldn’t advise having the Dad present, at least not for the entire party, but I would create an opportunity to have his presence felt. Here are a few ideas:

  • See if the Dad would like to pick up the tab for dinner, a round of drinks, or a bottle of the bachelor’s favorite spirit.
  • Ask the Dad to write a letter or film a video and give it to the bachelor during the party. Encourage him to be vulnerable, honest, and playful in the message to his son.
  • Invite the Dad to contribute a dare to the dare list (more on creating a dare list in a moment…).


Hold Space During the Party to Just Chill

When putting together a bachelor party, there is a tendency to fill every second with activity.

Resist that urge.

Instead, leave dead space in your plans. You’ll be surprised by how fun lounging around, having a few drinks, and shooting the shit with a cool group of guys is.

In fact, the story I started this article with, which was my personal favorite moment of W*’s bachelor party, only occurred because we had space scheduled just to chill.

These often become the memorable moments.

Create a Dare List for the Bachelor to Tackle Throughout the Party

To keep the party interesting – and to keep the bachelor at the center of everyone’s attention – I suggest creating a dare list that consists of challenges for the bachelor to complete throughout the party.

Reach out ahead of time to the guys attending the party, and ask each of them to come up with one dare for the bachelor. Tell them to keep in mind that the dare should make the bachelor leave his comfort zone, without being impossible.

One of my personal favorites from W*’s bachelor party:

“Every time W* orders a meal, he must stand up and high five the waiter.”

You can make the game even more engaging for everyone by adding the following elements:

  • A way for the bachelor to opt out of the dare
  • A way for the bachelor to reverse the dare by going above and beyond and enabling him to assign dares to the other guys in the group (if you do this, keep it a secret until everyone has arrived)
  • A reward for the bachelor if he successfully completes all of the dares without opting out

So an example of a fully formed dare would be:
“Every time W* orders a meal, he must stand up and high five the waiter.

Cost of opting out: W* must pay for dinner on Saturday night.

After two successful high fives, W* is off the hook. However, if W* gets every meal on Friday and Saturday, and the first drink order on Saturday night, he may assign a shot to S* [the guy who created the dare], and S* must high five the bartender when he orders for the rest of the party.”

If your bachelor is emotionally mature enough, it’s nice to have a dare that includes him sharing his favorite memory of each member of the bachelor party.

The real goal is to be creative and playful as you create challenges for the bachelor.

Get Organized Ahead of Time

Too often bachelor parties consist of a group of guys showing up and then winging it. Spur of the moment decision-making, especially with large groups, often results in lazy, lowest-common-denominator style decisions.

Instead, do a bit of work ahead of time to make the experience smooth and engaging for everyone. Most of the bachelor parties I’ve planned began on a Friday after work, and ended mid-morning on Sunday. I’ll assume that the one you’re planning follows a similar format, but if not, you can adapt:

  • Declare a clear meeting spot for Friday night. If you are renting an AirBNB have everyone arrive there. Be sure to have beer, liquor and cigars on hand for people as they arrive.
  • Friday night’s dinner and activities should be simple since people are arriving throughout the evening. I default to ordering a pizza and playing poker.
  • Saturday during the day, have one main activity. For W*’s bachelor party, we played soccer golf, but other activities to consider include: lazer tag, pitch and putt, batting cages, a video game tournament, floating a river, archery, hitting a local casino, go karts, a barcade, or bowling. If you choose a competitive activity, consider placing a light weight bet on the outcome to make it more engaging for the boys.
  • Saturday evening, the whole party goes out to a nice restaurant (be sure to make reservations ahead of time).
  • Saturday night, bar crawl. I suggest starting at a nice bar, and slowly working down from fancy bars to dive bars.
  • Sunday, for many people will be a travel day. I suggest an easy activity in the morning (breakfast, coffee, a round of cards, etc) and then declaring a hard stop time for the bachelor party.


Simplify Finances by Putting Everything on Your Credit Card and Divvy up the Total Later

If you’re rolling with a ten person bachelor party, it’s annoying to split the check ten times everywhere you go. Instead, put everything on your credit card, and then use cash, paypal, venmo for reimbursment.

This is easier for everyone involved (especially the waiters, waitresses, and bartenders). And of course, if you and the attendees can afford it, don’t let the bachelor pay for anything.

Create an Opportunity for the Guys to Raise Toasts and Share Memories with the Bachelor

A nice way to create a moment that the bachelor will remember forever, is to ask the attendees of the party to individually toast the bachelor or share one of their favorite memories of him.

Not all guys have the emotional capacity or willingness to do this. That’s fine. Vulnerability and honesty take courage. However, many of the guys will relish the opportunity to say, “I love you” without having to say, “I love you.”

Tell the guys ahead of time that there will be an opportunity to share stories and raise toasts, but there’s no pressure whatsoever to do this. If you’d like as many of the men as possible to participate, you should lead by example and go first. While this is easier for people after a few drinks just make sure it’s done before the bachelor is so drunk that he might forget.

***

The standard bachelor party is little more than everyone getting drunk in honor of the groom. Nothing wrong with that, but with a bit of effort you can create an event enjoyed by all of the attendees and more importantly, remembered by the bachelor for the rest of his life.

Read More By Jason Connell

Finding Your Deep Gifts in a Shallow World

Maslow Got it Wrong: What I Learned From Feeding the Homeless on My Birthday

How Should a Man Be at 30?

author_shot (1)

Jason Connell is a speaker and writer who teaches confidence, self-love, and self-compassion. He’s worked with everyone from Senior members of the Obama administration and professional athletes to middle school students and emerging entrepreneurs. He shares his thoughts on life, authenticity, and power at: JasonConnell.co.
 


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