My little brother is getting married in April and I'm the best man for the wedding. I'm planning for a bachelor party during the middle/end of April and wanted some help figuring out the idea I have in my head with people who aren't complete degens like me.... (Skip to other activities if TLDR)

First a little about the groom: Does not want to know anything about the party, or the details. I think some of it is a mix of he wants to be surprised and some of the he can't be held responsible for what happens then. The bride to be is pretty awesome and has already given me the go ahead on the side to basically do whatever, including strippers, should we wish. My brother is not your typical guys guy and doesn't have many male friends so a lot of the invite list is family with a few friends sprinkled in. The other problem is a large portion of the invite is is out of town and while they will come in for the wedding won't be in for the bachelor party. The only real interest he has that would be applicable to this type of party would be he loves whisky.

My thoughts: All day extravaganza. Ideally we'd start with something fun that I can include some of the younger (under 21) family members in. Paintball, go karting, whirley ball, etc. then head out for a nice steak dinner somewhere, then an evening back at my brother's (or someone else's) house since mine isn't big enough to host that many. .

Incorporation of whisky: My thought is instead of having people show up with stupid gag gifts would be to bring their favorite bottle, or a bottle if they don't have a favorite, of whisky so we would end up with a lot of different kinds and can do some tastings throughout the evening. My brother can then keep the leftovers.

Other Activities: This is where I need your help. My brother only somewhat likes to play poker, usually with friends and family for super small stakes, so I'm hesitant to do "just" poker. Instead my thought was to set up a casino night with a poker table for those that want to play, and a few other table games.



My concerns/Issues

1) Fake money or real money?
I hate "fake money" anything so I'm opposed to this, but I thought for this type of thing that it could potentially work. People bring $X dollars (not even sure where I'd put $X ($20-$60?) and you'd get X amount of chips to play games with. If you go busto, you'd have to do something to get more play chips. At the end of the night we could award prizes for the most amount of chips. What type of prizes would be good here?

If I went the real money route I'd keep it friendly so bets allowed from $0.05-$5 and I'd bank as the house for the evening. Poker game would be $0.10/$0.20 with a max buy in of like $10. I think some people would prefer this as there is real money at stake, but I might have a few that could be opposed to it as it is "real gambling". Also how would this work with the bachelor? The other way it would be easy to just give him a stack like everyone else and not charge him anything.

2) Length
How long do you think the average person would want to spend doing something like this? I figure if we get back from dinner at like 8ish. This could take us till 11, when most of the older folk would be heading out and then after that we could play pool, darts, poker, video games, or hang by a fire outside if the weather cooperates.

3) Topless waitress
I don't think my brother would be cool for strippers, but I think this is something he would like. I'm not sure if I'd want them dealing as I thought it might be better to have them bringing drinks, etc. all night. One potential issue with this is it drives the cost way up as you have an initial expense, plus tips throughout the evening.

4) Dealers
I have a pretty large home game group and could probably get some people to help out here that would probably love to do something like this for little cost. If I couldn't get this to happen, then I might have a few of the attendees take shifts, or possibly use girls for it.

5) Equipment
A major issue here is actually getting the set up for some table games. I don't want the crappy plastic mat crap or cheap stuff as this is my brother and if I'm going to do it I'm going to do it right. Renting equipment is a possibility, but upon my initial looking it seems like most rental companies are renting out half ass equipment at the rate it would cost to build a nice set up. There is a possibility I can ask around from my poker group and maybe find something that I could borrow for the night on the cheap, but I don't know right now on that.

I have the capabilities of building a blackjack table, or a let it ride and was thinking I could do two of them at the same time since the set up would be identical. The downsides are that I really don't have the space to keep them and I don't think my brother would want them. The time commitment is large on this and that I will be out $300-$400 for materials for two tables (would be my guess). My thought was that if I go with a "fake chip" set up that I could take some sort of "rake" (excuse me while I beat myself for thinking about it) to get about half of it covered. Ex. If we did a $40 to get into the pool that I would put $20 back in prizes for each person.

***Possible thought that could potentially solve some of the problems. Maybe give away one of the table as a prize? Sell the other to help offset the rest of the cost.

6) Overall Day Cost:
One concern I have is overall cost for both myself and attendees. I don't want cost to be prohibitive to guests and with some I'm not concerned at all, but I'm not sure what's reasonable in terms of cost for everything. This is the first one of these I've had to plan and things were different when I got married 7 years ago as my brother was my best man, but he was only 20 at the time and the whole thing got paid for by my parents....

In chunks everything expensewise seems reasonable, but when I add things up....paintball $30-40, dinner $30-40, bottle of whiskey $40-100+, evening $60-$100 if we have some girls the whole day could become quite expensive....



Anyways that's what I have right now. HALP.

Much of this you admit is not your brother's cup of tea. Poker and strippers as examples. Yet you want to provide those anyway. Why?

I know you propose to add other games like blackjack. Does he like blackjack? Is this a real passion for him? Even if so, will everyone else want to play that, or will they gravitate to a poker table, leaving him out of the action?

Sorry, dude, but I advise you to drop from your plans anything that he is not into. Don't let poker take over what should be all about him.

I probably didn't give a good enough description of him in the OP. I'm sick and had just gotten done with my musical yesterday so my head was all messed up.

It's not that it's not his cup of tea so to speak, but that he doesn't like gambling things for anything more than a small amount of money. For him a lot of it will be just bring able to spend time with people in a close environment. My issue is I'm feeling extremely limited because of the time of year (Chicago area in March the weather is a crapshoot) and even still he wouldn't want to go golfing or to a bar.

He likes to gamble but is usually too cheap to do so. I probably should've included that I floated the casino night/whisky thing by the bride to be and she thinks he would love it. he thinks he would like this type of evening, even if he isn't saying it.

He does like blackjack a lot. We used to play for hours on road trips when we were kids. Of the people coming more would probably like the table games as opposed to the poker, but as my brother also likes playing (but again only with family and friends, which would be this group) I thought we could include it.

As far as the girls. I need to get a definitive answer from him on this. I know he wants to stay out of planning it, but I want him to have a good time and be comfortable so I'm going to make him give me a straight answer. If he wants them I'm happy to provide them in whatever capacity (strippers, or just dealing/waitress) or just not have anything like that if he doesn't want it. I just included it in the OP as it is still a possibility.

Ultimately the day is about him and making sure he has a good time which is my number one priority.

Blackjack neoprene table toppers are available online for much less than what it would cost to build a table, around $50-55 shipped, and they can be rolled up for easy storage.

Cdnmoose has posted a bunch of details on CT for the some of the casino nights that he and MrsMoose have hosted. They sound like a blast. He might be willing to share some of his ideas with you.

Hope you're feeling better.

Good thought and derp on me. I own one.....

Okay, so with a better picture of his preferences, this could work. As long as there will be people to play blackjack with, and the stakes will make poker fun for him, it should be good.

Carry on.

sounds like you're in a good spot to provide some of the "cutting loose" thrills he normally denies himself. Keep the gambling lowish-stakes (low risk to hero, anyway -- give him a discount/freeroll?) and the nudity within the zone of comfort, but seems like your role is to generate activities in the area between the thresholds of what he'd be willing to ask for and where things get too wild to enjoy.

Paintball for $30-40 is insanely cheap where I'm from, that wouldn't last most people 15 minutes? Just warning you.

That's the perfect description of how I see things my role in all of this. Give him a chance to have more fun that usual, but not be over in the deep end on things.

Yeah we've done this before as a group and the cost might be slightly more, like $40-50, so yeah its cheaper, but than again we don't go with full autos either


Other Thoughts
Below is part of a conversation I was having through email with abby99 on somethings that I'm looking for more feedback on.


I'm leaning towards fake money for the evening and maybe just doing
the flat buy in, with cash or other cool gift prizes going back to the
winner, or others via lottery style. I thought about doing Pai Gow,
but table game style with a dealer. If I ended up building two tables
I would probably use this as the second one.

A few more things I'm trying to work out:

1) Rebuys, I don't want to deal with them all night so my thought was
to come up with something like spinning a wheel of chance to earn
extra dollars that could include some bad things if people go busto.
My hope is this discourages the stupid bet the max every hand crap,
although towards the end of the night that will be expected.

2) Chips. Not sure if I have enough in the customs to make this work.
With the $1, $5, $20, $100 I'm looking at like $17,700 in 2000 chips
and probably like 10-15 people. The issue is: Having enough change in
the dealer racks to accommodate all the bets + 1700 chips are $3,700
of that bank. I have a tournament set that has $500,$1k, $5k denoms,
but they might be sold soon so I don't want to count on them.

3) Number of games: Not sure how many I will need if I'm thinking
10-15 people. I'd kind of like people to play what they want, when
they want, but also make sure there is enough people at ever game that
it will be social. I'm shying away from a rotation here as it seems to
"structured". What would be a good number here? Poker + BJ + Something
else or maybe skip poker and just play "house" games?

Consider pit games only (no poker) if you want people to move around and try all the games. If you want around four people at each game, n/4 games seems about right. BJ and Pai Gow Poker are easy to learn, and both are very social games. Roulette (use an electronic wheel) and/or craps might be good to consider if you could pick up layouts and do a makeshift craps table (assuming you're not renting equipment).

If you think a night of gambol on the cheap will entertain skip poker.

Have a casino night and bring the "Vegas Bachelor party experience" to him. Play for monopoly money with prizes (bottle of booze, free buyin to a tournament, free lap dance if strippers are involved) awarded to biggest winners. You can allow people to "buy" back in by completing "challenges" or something. (Crowd dependent but like having to streak or something) The bachelor starts with double and has a never ending supply of "rebuys"

Save the real money for funding the girls/dealers/food/booze.


Paintball is always a blast with bachelor parties. Been to two that did it. Both were awesome.

ETA: You could even look into a company that does casino nights. They'll provide dealers/tables and enough "cash" and chips that you don't have to worry. Plus they'll run the show so you can enjoy the games and not worry about the logistics as much.

Not sure that would be cost effective but certainly worth a look imo.