Asking a friend to be your best man can be a little scary. You may worry that your friend will not want to be the best man and that you will feel embarrassed for asking. As men often have trouble expressing emotions, you may find it easier to poke around to see if that friend is interested before formally asking him. Most of your close friends would probably be glad to be your best man, but there are certain duties that they may not be comfortable with. So be sure to address the specifics of the best man's role.

Meet up with your friend for a face-to-face conversation about the wedding and his role. Pick a place where you can have a conversation without yelling, such as a quiet restaurant or a coffee shop. The conversation could be casual; if the friend is close, you could ask him in passing, as he may already be expecting to be asked at some point. Ask your friend if he is interested and what he thinks of the idea. Speak about why you chose him and discuss what he will need to do to fulfill his duties as best man.

Call your friend on the phone to ask him to be your best man. Phone conversations lower the fear of confrontation or rejection. Discuss his duties and make it clear that he is in no way obligated to say yes. He can politely decline. Explaining why you have chosen him will make him more likely to answer in the positive. Phone calls are less personal than face-to-face meetings, but schedules often dictate them.

Send your friend a card or a letter asking him to be your best man. If circumstances prevent you from reaching the potential best man in person or by phone, send a card or letter about it with a description of the duties to help him make a decision. This approach eliminates any knee-jerk reactions and allows the friend to contemplate the offer and mull it over before making a final decision.

Send your friend an email about the wedding expressing your wish for him to be your best man. This approach is similar to sending a letter but is more convenient and instant. Let him know that you appreciate his friendship over the years and that you would like him by your side as you go through this exciting time. Let him know there is no pressure but that there are tasks he will need to complete, including planning the bachelor party and assisting the other groomsmen on the day of the wedding.