How to ask someone to be your best man is not easy, especially because we are men. Men as a whole like to avoid such things, and often wait until the last minute to ask. This is where the happy bride-to-be steps in, and through constant reminders, the difficult question gets asked.
The fear of asking exists on a number of levels. Unlike the marriage proposal, where the fear of rejection figures prominently, asking your best friend to be your best man brings out fears that you may appear overly sentimental, especially if your relationship with your friend, close as you may be, is based on a manly lack of emotional expression. This is not the same as your wife asking her friends to be part of her bridal party, that has usually been discussed ahead of time. Instead, you've already got a set of close friends, but usually it's not easy to tell which of your close friends you'll end up picking. Let your finance worry about her wedding party and instead you focus on your wedding and the most critical guys that will be a part of your wedding day.
There still exists this silly fear of asking the closest guys in our lives to be just that, a close friend, and be a part of our wedding. There are many ways one might be asked to become a best man, and it really depends on the personality of the individual asking, and the personality of the individual being asked.
Who to Ask
For the most part, people tend to have associations with people of the same temperament or of like personality, but I won't go into that because then this would be a book on psychology and not about men and weddings. Of course, such is not always the case. For example, a strong, outwardly-confident man might simply instruct his quiet friend that he is to be part of his wedding, whereas a mild, meek individual might have a lot of trouble approaching his more dominant friend to ask him to be his best man. If it's your brother, that might be a whole different dynamic, and frankly more natural. Just go with what's natural.
The bottom line is that a wedding is an extremely important occasion and the question, however it comes, may have not been so easy to ask. As men, a fact that few women know, we possess a special form of communication with each other. A sixth sense if you will. We can usually tell, for example, what the other is thinking when a beautiful woman walks into the room. Then there's those brief gestures that we share across a crowded room, trying to scope out location or favorites in the crowd, gestures that no one else may understand or even notice. Then there are team sports. Here we have the innate ability (some more than others) to be able to make a blind pass or shot to a friend, knowing without question that he is there. It is for these reasons that when it comes to important questions in our lives, we often leave them unspoken.
Reading His Mind
We assume that our friend will know exactly what's on our minds. After all, we are men. This, however, does not always work, blame it on bad connections if you will, and so we are forced to put our thoughts into words. Many of us will simply blurt it out in a single breath. "Hey, I'm getting married, want to be my best man?" "Sure." Others will take the scenic approach. "Hey, did you see the game last night, wow, I can't believe they won." "Yes, what a comeback." "Oh, by the way, I asked Deb to marry me, and she said yes. Want to be my best man?" "Sure."
Asking a Work Friend
Then there is the more cordial or professional route. "It is determined on this day, by myself and my bride-to-be, that on the sixth day of December, in the year of the Lord 1998, we shall be wed before the eyes of God, and a number of close friends and family. It is thereby sworn to ask you to be in attendance on this occasion to serve as my best man. That is, of course, if you would be sporting enough to patronize us on this day with your approval?" "Jolly good of you to ask."
The sentimental path:
"Well, we've been friends for a very long time, and well, it just wouldn't be the same if you couldn't be there to be a part of our wedding. I think of you, not only as a friend, but as a brother, and that, well, I love you man. Would you be our best man?" Sniff, sniff. "Sure." Of course, your friend may not personally tell you this in words - men seldom do; however, I am quite certain that this is what has been left unsaid and articulated through some passive grunts and maybe even a handshake or a hug. Then we will immediately turn the conversation to sports. The "I've known you for a long time" approach. "Well?" "Of course." The "we've been friends forever" approach (like a couple of mimes without the make-up or silly costumes). The groom-to-be approaches his friend, who gestures to him that there is a pretty girl across the street. The groom refuses to look. His friend, surprised, raises his eyebrows and shrugs his shoulders in a "really?" matter-of-fact way. The groom nods in assent, to which his friend smiles and extends his hand to congratulate his friend, patting him on the back. The groom then lowers his eyes, and stumbles in his motions, kicking a stone on the ground, as if he wants to ask his friend something difficult. His friend senses this and places his hand on his friend's shoulder. Their eyes meet and the groom offers the expression of "well," to which the friend happily nods. This done, they shake hands again and the friend tilts his head in the direction of the street and the two leave for a celebratory drink.
You should also put some thought ahead of time as to what their responsibilities may be before the wedding and on the wedding day, so you'll manage their expectations up front. It could be that you want them to help the maid of honor with the rehearsal dinner. Or it could be that you want them to do something specific at the wedding ceremony. Organizing the bachelor party is also something they're likely to do, but don't assume that they'll do it. Ask them. The one thing they know they'll have to do is the speech. So don't forget to mention that. The best man speech is something that usually a critical part of their role, besides being with you at the altar.
The ESP route: If you stop and think for a moment how your friend initially asked you to be his best man for his wedding, you may actually get an idea as to how difficult it was for him to ask. That being said, he is extremely glad that you said yes, and realizes that it wasn't so very difficult after all. Now that you have been asked to perform this honorable duty on your wedding, you realize that you have no idea what to do, and you didn't bother to factor in this variable when you so quickly answered your friend. What's next? Don't forget to get the lucky groomsman a best man gift ! That might help you out when popping the question - to him, of course.