It was a blast, a shindig, a hoot and a half. My brother's bachelor party was by average measures a success, meaning that everyone who stuck around had a good time. We did lose two guys along the way, but I think that had more to do with priority differences than party plans. Overall, I was happy with the results, and more importantly, so was my brother.
I hereby admit, however, that it could have been more spectacular. To that end, I've made a handy guide for future Best Men in their own efforts, using both things I learned along the way and my blinding 20/20 hindsight. I did try to keep it down to ten items, but I just couldn't cut any content. Top ten lists are overrated anyway.
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Best Man's Guide to Bachelor Party Planning
1. Plan Ahead: Whatever the plan, know it and communicate it in enough time that everyone has enough notice to both show up and afford it. A month lead (or two paychecks) time is a good start.
2. Make at least one part of it classy: Even if you're planning a raunchfest, at least have dinner somewhere he can bring his soon-to-be wife later on. It's just good taste, and if nothing else provides the guys with a segment of the evening they can be completely truthful about.
3. Delegate: Make the other groomsmen do parts of the job, especially if they have a passion or expertise that fits. If a guy plays in a band, or knows someone who does, make him plan the bar leg for instance. Also, see rule 9: Police the party.
4. Share the cost: It's not tacky to ask for guys to pay not only their own way, but part of the groom's. You shouldn't be footing the whole bill just because you're the best man, and the groom should have to pay exactly zero all night. Be up front about this with the guys and they'll not only appreciate the effort you're making, they'll all have a better time.
5. Designate drivers: Volunteers are preferable. If nobody steps up, you're the first DD of the night (like it or not). The bachelor gets shotgun, always. Also see rule 6.
6. Stay cogent: Even if you're not a DD, you can't afford to get sloshed. You've got a lot to keep track of, and you owe it to the groom to make this the best night you can. Drinking yourself into oblivion is a good way to lose track of this responsibility.
7. Know what the girls are doing: Not necessarily to match or one-up the bachelorette party, but at least give something comparable. If they're wearing custom matching bar shirts with "Bride" and "Bridesmaid" sequined to the chest, the least you can do is make souvenir beer koozies. Anything less will only make comparing stories later a lame reflection on you.
8. Take pictures: lots of them, digital ones, so you can delete them when you're sober. Chances are you'll probably get lots of keepers along the way.
9. Police the party: if anyone looks like they might be trouble, be ready to either confront them or put them out without making a scene. Don't let anyone get out of hand, especially where strippers and waitresses are involved. Don't let the bachelor do anything that might sabotage the wedding should a story, video, or picture fall into the wrong hands. If a man can't rely on his friends to keep him out of trouble, he needs new friends. Again, see rule 3: big guys get cop duty.
10. Watch the bachelor: Keep track of how much he's had to eat and how many drinks, and know the signs that he's done for the night. When he's near critical mass, cut him off and move him to the pool table so he stays on his feet and you can watch him more closely. Also, keep water and paper towel in the car, in case you end up missing the signs.
11. Have the toast and coffee ready: wherever the bachelor's going to crash, in case he gets really drunk. Maybe plan to end the party at an all night diner. Have a trash can near the bedside, too, and make sure he's well cared for 'til morning.