It’s not rocket science. You pick your brothers and your buddies. Simple. Sometimes, however, there are tricky questions. Find the answers here.

In a wedding ceremony, the best man is the guy who—just kidding. You get it. This stuff isn’t neurosurgery. Inevitably, however, you’ll have some tricky questions about who to pick, how to “break ties” of friendship, and how to avoid bruised egos. You’re bound to wonder, “Yeah, but my situation is different. What if….”

We get it. Picking your groomsmen can be difficult. You have questions. We have answers. And if you have something that’s not listed? Just Ask The Expert and we'll get back to you, promise.

What if my fiancée hates one of the guys…can I still choose him to be a groomsman?

Maybe she has a legitimate beef. Let’s say that early in your courtship, she overheard one of your buddies call her “Big Nostril Girl” or predict that she would probably “take it in the pooper.” You can’t un-ring that bell. If one of your friends has given her a credible grievance—either an isolated episode or a pattern of disrespect—then it’s your duty to defend her honor and black-ball your friend. Sorry. You just left the world of bros-before-hoes.

That being said… if she simply doesn’t like the way your buddy chews his food, or maybe she thinks he drinks too much, talks too loud, passes gas, or that his receding hairline will tarnish the wedding photos? Tough. Barring the aforementioned scenario, you are within your rights to select whomever you’d like. Don’t back down.

Smoothly employ this kind of argument: “This will be the most important, happiest day of my life. I love you so much. And I want to share this moment with my closest friends—the good, the bad, and the ugly. I know Billy’s kinda rough around the edges, but that’s how much our ceremony means to me.”

What if my best friend isn’t really up to the task?

Most of the wedding-porn says that you should look beyond mere friendships, and that if your very best friend in the world—Pothead Chucky, your old freshman roommate—isn’t that reliable, organized, or mature, then it’s better to select someone more “appropriate,” even if you’re not lifelong friends.

Our response? Horseshit.

This mindset suffers from the typical wedding-porn propaganda, the mindset that weddings are so complicated, so all-consuming, that it should gobble up your every day for the next 12 months. Let’s get some perspective: your best man should be your brother or your best friend. Period. His responsibilities as the best man aren’t really that complicated (click here for the rundown), and if there’s anything he can’t handle, you can simply do it yourself or delegate to another groomsman.

What if I have two equally best friends? I don’t want to insult or reject either one.

Do you have a brother?

Yes.

Pick him. Done. Simple. Your friends will understand that blood is thicker than beer.

Wait, I forgot, I don’t have a brother.

Then you have two choices. If their egos are so fragile that they absolutely can’t be snubbed, then you can go all new-agey and say that you have Best Men. Carve up the best man duties; one plans the bachelor party, one holds the rings, they both give toasts.

You could do that.

You could also call each other BFFs, air-kiss when you greet each other, and paint each other’s toe-nails a nice shade of violet. We’re men. We’re above this junior-cheerleader-squad political bullshit. So plunk down a simple, objective tie-breaker that no one can dispute: give the nod to tenure. If you’ve known one buddy for 7 years and the other for 3, just go with the 7-year-guy. Be honest with your friends; tell them that if possible, everyone would be Best Man—you’re all equally good friends—but since this stupid ceremony makes you pick just one, you have to go with the guy who has seniority. And that’s that.

What if my best friend is a girl, and she wants to be a groomsman?

Go for it. This has become more and more common; as long as your fiancée or family is comfortable with the gender mash-up, there’s no rule against it. Alternatively, you could have her as one of your fiancee’s bridesmaids, but that sort of seems dishonest and dumb, right? She’s your friend, not your fiancée’s—if possible, keep her on your side of the aisle. It’s not like you’ve slept with her.

….uh, but what if I’ve slept with her?

Then don’t use her. Even if your fiancée says that she’s cool with it—and even if she thinks she’s cool with it—she won’t be. (This is a lot like inviting an ex to the reception.)

What if I want five groomsmen and she only wants two bridesmaids?

You can—and should—communicate your preferences, but when push comes to shove, she’s the one who will drive this decision. Remember, the bridesmaid costs (driven by the dresses) will dwarf the grooms’. So give her some leeway here.

What if I’m not that close to my brother?

Do you have one or not? Damn. Make up your mind. Okay, the first thing to remember is that “best man” is an honorary title. It doesn’t necessarily mean squat. I’ve been to plenty of weddings where the best man was a brother—in many cases a distant, estranged brother—and the groom leaned on his friends for everything else. It’s sort of like how in the first few seasons of The Sopranos, Uncle Junior was officially the head of the family (to throw off the feds) even though the real power rested with Tony.

Alternatively, you can use him as a groomsman and tap your best friend as best man. But unless you truly hate his guts and want to send a message of spite… never banish him from the wedding party altogether.

What if she wants her brother to be a groomsman?

You’re probably screwed. There’s no clean exit from this jam. If she absolutely insists that little brother Timmy is a groomsman, your refusal could win the battle (of the wedding) but lose the war (of your in-laws). Plus, the unwritten rule is that you take her brother as a groomsman. It's a dumb rule. But it exists.

You have only one possible card to play. Instead of framing her brother as a negative, frame the other groomsmen as a positive. Go with: “Hey, I would love to have your brother as a groomsman, but Peter, Greg, and Bobby are my three closest friends, and it’s really important to me that I have them by my side, up there at the alter. I’ve dreamt of this day for years.” This isn’t guaranteed to work, as she could suggest expanding the roster to four groomsmen. But it never hurts to try.

What if I don’t have three good friends, a la I Love You, Man?

Two pieces of advice. One: more going to bars, less World of Warcraft. Two: if you simply need more bodies to stuff in tuxedos, the first place to look is your brothers, then male cousins, then her brothers or male cousins. Reconnect with your old best friend from college. Use your father as best man (The girls will oooh and ahh and think that’s cute as shit.) Truly desperate? Just slash the size of your roster. Even Kip from Napoleon Dynamite could rustle up two friends.

Next groom duty: planning the honeymoon.

For how the groomsmen should behave at a bachelor party, click here.

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Addendum: a Plunge reader wrote us at Drowning@ThePlunge.com, asking how to choose between two brothers and a best friend that he's closest to.

Our response:

If I can read between the lines a little bit, it seems you really want to pick your friend as best man but are worried about your brothers' reaction. While The Plunge would typically recommend you pick your brother (singular) over a friend, in this case, it's really quite simple: since you can't be expected to choose one of your brothers over the other, you will treat each of them equally as groomsmen, while opting for a neutral friend as the "best man." They should be understanding of this. You could say something to them like "If I could have 2 best men I would, but that's not how it's done in weddings."

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