Fun can mean so many different things, depending on your outlook. Bachelor parties are supposed to be all about cutting loose and having a good time. But there's a difference between having fun and crossing the line into questionable territory. You're walking on thin ice, whether you realize it or not. Proceed cautiously.

Fun vs. Making the Bride Cry

Know your bride; know what she will tolerate and what she won't. If you're engaged to an incredibly open-minded woman who loves experimentation, you're in a very different boat from the guy who's engaged to a conservative woman. Your fiancée is not going to change her colors simply because you're off to your bachelor party. You're her now and forever man, and she has certain expectations of you.

If you're engaged to a girl who's on the more reserved side (i.e., she doesn't like strip clubs and she isn't thrilled with the idea of your being out-of-your-mind drunk), think carefully about your bachelor party, your expectations of the event, and how it could affect your relationship with her. Some women are very opposed to the traditional bachelor party, as they feel it's antimarriage. If your own bride-to-be feels this way, you're going to need to watch your step so that you're still engaged the morning after the big shindig.

How can you accomplish this? For starters, you need to trust the guys who are planning your bachelor party. If your wild brother is in charge and he has a penchant for loose women and illegal activities, think again before you agree to put yourself in his hands for the night.

If your pals keep telling you that the whole night is a big surprise — and you're going to love it — be a little leery. Chances are they know how your bride feels about the whole event. That doesn't mean they're going to respect her feelings. Believe it or not, sometimes friends really resent the appearance of a girlfriend or wife in the picture, and they'll do anything to come between the two of you.

Worst-case scenario (for you, anyway): You find yourself somewhere you know you shouldn't be. Maybe you're sitting in the middle of a strip joint and there's a scantily-clothed woman dancing on your lap. (You get the picture.) You have two choices: stay and revel in the fun (and remember, that word has different meanings — your bride won't accept the excuse that you were just having “fun”); or leave, and risk being called a wet blanket.

You know the right thing to do (as you hear your fiancée's words, “No strippers!” echoing in your head) is to leave, but the fun thing is to stay. You're a grownup. You have to make this call on your own. Chances are if you're three sheets to the wind, you're not going anywhere, and if you're sober … you might. Just remember this: The bachelor party is supposed to be fun. It's not supposed to end your relationship.

Walking the Line

How are you supposed to know what's acceptable behavior and what's going to leave you stranded in the dog-house? Turn the tables for a minute.

Look at your bride. She's beautiful, she's smart, she has a great sense of humor … she's a real catch, and any man would be lucky to have her, right? In fact, sometimes you can't believe she agreed to marry you.

Now picture her engaging in the same activities that you have in mind for your bachelor party. (That mental picture you have of her at her bachelorette party, stuffing dollar bills into some guy's g-string — using her teeth, no less — isn't such a pleasant image, you say?) Life isn't about keeping score, of course, and/or one-upping each other. But in this case … maybe it's the best way to judge what's acceptable and what's not.

Talk It Out

Some grooms avoid discussing the bachelor party with their fiancées precisely because they'd rather not know where the line in the sand is drawn — because if you never hear your girlfriend say that she disapproves of certain activities, you can't be held accountable for taking part in those activities, right?

Wrong. Since you are preparing to walk down the aisle soon, you probably have a pretty good idea of where your fiancée stands on certain issues, like excessive alcohol consumption and strippers. By pleading ignorance after the fact, you'll only be digging yourself in deeper. She's not going to buy that excuse, for starters, and she may begin to question why she's marrying a man who doesn't have a clue about her feelings.

Keep in mind that your fiancée is running on emotional steam in the weeks preceding the wedding, and any inappropriate behavior will be under the microscope at this point in the engagement, as she wonders if she even knows you and if you intend to behave this way after the wedding.