The Best Man's Hidden Burden
Congratulations—you've been named best man. It's an honor. It means your friend trusts you more than anyone else to stand beside him on the biggest day of his life. It also means you've just inherited the unpaid role of event planner, budget manager, and debt collector for a party that could cost thousands.
Here's how it typically goes: you pick a destination, book the house, reserve the activities, and put it all on your credit card. Then you send a neatly calculated breakdown to the group of ten guys. Three pay immediately. Two say they'll "get you next week." The rest? Radio silence. And now you're $3,500 deep with a credit card bill coming.
This pattern is so common it's almost a rite of passage. But it shouldn't be. The best man is already coordinating logistics, managing personalities, and making sure the groom has the time of his life. The last thing he needs is to also become a human bank account.
Why Bachelor Parties Get Expensive Fast
Bachelor parties have evolved from a dinner at a steakhouse to multi-day destination events. Vegas weekends. Lake house getaways. Golf trips. Fishing charters. Each of these involves layered costs: the rental, transportation, food, drinks, activities, and the inevitable "spontaneous" expenses that happen when a group of friends is celebrating.
A typical bachelor party for eight to twelve people can run anywhere from $3,000 to $10,000 in shared costs. Split evenly, that's $300 to $800 per person—real money that needs to actually change hands, not just get promised in a text message.
The problem compounds because bachelor party groups often include guys from different parts of the groom's life who don't all know each other. College friends, work buddies, cousins, the bride's brother. They don't all have the same communication style, the same budget, or the same sense of financial urgency. The best man has to wrangle all of them.
The Guy Who Shows Up and Doesn't Pay
Every bachelor party has this person. He's the first one to say he's in. He's the loudest one at dinner. He orders top-shelf and suggests renting the boat. And when it comes time to settle up, he's got a thousand reasons why he can't pay right now.
The social dynamics make this incredibly hard to address. You don't want to cause drama before the wedding. You don't want to put the groom in the middle. And you definitely don't want to be the guy who turns a celebration into a collection effort.
The only real solution is prevention. When financial commitment happens before the party, not after, this person either pays upfront or self-selects out. And honestly, both outcomes are better than the alternative of chasing them for three months while pretending everything is fine.
Collecting Upfront with Pooled
Set up a pool on Pooled with the total estimated cost. Be specific in the description: "Jake's Bachelor Party - Lake Tahoe. Includes house rental ($3,200), boat charter ($800), groceries/drinks ($600), poker night buy-in ($200). Total: $4,800. Per person (8 guys): $600."
Share the link in the group chat. Set a deadline that gives you enough time to book everything. And then step back. The pool shows everyone exactly what's needed, who has contributed, and how close you are to the goal. No more personal Venmo requests. No more "just a reminder" texts.
Here's the power move: don't book anything until the pool is funded. When you tell the group "I'll lock in the house once we hit our target," people have real motivation to contribute. The party literally depends on everyone doing their part. That's a lot more compelling than a Venmo request with a palm tree emoji.
Budgeting Smart for Every Price Range
Not every bachelor party needs to be a $10,000 blowout. Some of the best ones happen at a buddy's cabin, in a backyard, or at a local golf course. The key is matching the budget to what the group can actually afford—not what Instagram says a bachelor party should look like.
Before you plan, have an honest conversation about budget. Create a quick anonymous poll if needed. If half the guys can do $500 and the other half can do $200, plan for $200. The point is to celebrate the groom, and you can do that at any price point.
Pooled works at every budget level. A $1,500 pool for a backyard barbecue with poker is just as easy to set up as a $8,000 pool for a Vegas weekend. The platform doesn't care about the amount—it just makes the collection seamless.
Covering the Groom's Share
Tradition says the bachelor party crew covers the groom's share of expenses. This is a nice gesture, but it needs to be factored into the math from the beginning—not tacked on as a surprise after people have already budgeted.
When you set up your pool, include the groom's share in the per-person calculation. If the trip costs $4,800 for eight people, and you're covering the groom, divide $4,800 by seven instead of eight. That's $686 per person. Be transparent about this: "This includes covering Jake's share because he's the guest of honor."
Surprises are great for party planning. They're terrible for financial planning. When everyone knows the real number upfront, nobody feels ambushed, and the gesture of covering the groom feels like a genuine group effort rather than a financial gotcha.
Make It About the Groom, Not the Money
The whole point of a bachelor party is to give the groom an unforgettable experience with his closest friends. When money drama enters the picture, it takes the focus off him and puts it on spreadsheets and IOUs.
By handling the financial side cleanly through Pooled—transparent, upfront, and fair—you free everyone to be fully present. The best man isn't distracted by outstanding payments. The group isn't divided by who paid and who didn't. And the groom gets exactly what he deserves: a weekend where his friends show up, fully committed, ready to celebrate.
That's what being the best man is really about. Not managing money. Not chasing payments. Just making sure your best friend has the time of his life.
