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DH as best man.....round #2
DH's BFF just got engaged last night and asked DH to be best man. Again. This is engagement #2...he has a marriage and divorce on his record already (married at 25, divorced at 27, now 29.) The funny thing is I was just telling someone last night that it would be a LONG time before this guy got married again. He was probably proposing the second I said that. :-)
So....can DH just repeat the same bachelor party?? Haha. I'm not sure what the etiquette on all this is... It sounds like the wedding will be in August 2012 so I guess we have some time to figure it all out...unless the world ends by then? 
eta: The funny (sad?) thing is that the newspaper article about his first wedding is still Google-able. They got married on 07/07/07 and the paper did a story about it. Man how things can change in 3.5 years! (I won't link as there are full names in it.)
Re: DH as best man.....round #2
Well, let's hope that second time's the charm - for your husband's friend and for you Marcy (Congrats! btw).
I have a "friend" from HS that got married the summer before I did - almost five years ago. My BFF was her MOH. She divorced before her second anniversary - and considering that 6 months after her wedding she wasn't wearing her wedding ring and was sleeping in a separate bed from her husband - I'm shocked they eeked out two years! Less than two years from her divorce and she got engaged and is getting married again in a few months.
And my BFF who was her MOH? She hasn't spoken to her since before she got engaged (over a year ago) and basically is cut off from EVERYTHING with his friend - the girl won't even respond to her emails. Really sad because they had been quite close (obviously) - but BFF thinks that her friend doesn't want her involved in the second wedding because she (BFF) knew all the dirty details from the girl's first marriage and knew that the girl pressured her ex into marriage and that it was essentially doomed from the start. So rather than own up to the fact that maybe - just maybe - she was partially responsible for her first marriage falling apart, this girl would rather cut off one of her best friends and pretend the friend - and the first marriage - never existed. Crazy!
Anyhow - - if you search her on the Knot's wedding website thingy, you get her FIRST wedding and now her SECOND - nicely listed in order. June 2006 and June 2011. You'd think she'd at least want to remove the previous listing - she removed everything else from her past life without any hesitation . . .
I regards to the bachelor party, though....
I would think a lower key party would be fine. A simple BBQ and lawn games, etc. I don't think there is a need to do a stretch limo and go to the b00bie bar.
Actually after I posted this last night DH talked to his BFF (R) and R said he and his new fiance want to get 5 couples together and go somewhere fun for a weekend - like an informal joint bach/bachelorette party! That sounds like fun!! Chicago is pretty central to everyone so that might be the spot.
I agree...no limo and booby bar - they did that last time. :-)
I've never been to a 2nd wedding so close to the 1st. Half of the guests will most likely be the same from the first wedding. It just feels a little odd to be doing it all over again this soon but that's the way the cards fall sometimes... The bride is 25 or 26 and it's her first wedding so naturally she wants to do a "big" wedding. Should be fun no matter what...we already know his family knows how to throw a great wedding.
I'm Andy's second wife, so our wedding was his second, but my first. He got married very young, right out of the military, to his first serious girlfriend. They were married 15 months - wedding in 2000 and divorce in 2001.
In any case, neither Andy nor I were interested in typical bachelorette/bachelor parties before our wedding. Some friends hosted a BBQ at their house, so we just did a relaxed BBQ & yard games kind of party in place of bachelor/bachelorette parties. It was super fun and much more our style.
Mr. Sammy Dog
That sounds like fun!
Also, super cheesy, but my mom did the Chicago city tour via Segway with her girlfriends a couple years ago and they all loved it. If the H and I ever go for a weekend, we will definitely do it, too.
If you're interested, they ask for reservations. Here or here, or here.