The rules for pairing bridesmaids and groomsmen are many and varied. In the past, when traditional weddings were the order of the day, it was assumed that the groomsmen would escort the bridesmaids and was understood that an even number of each would make the task simpler. In modern times, with weddings often held in more informal settings, the expectations are not so clear. While no hard and fast rules exist and it is left to the personal preference of the bride and groom, many still prefer to take the traditional route.

Many brides ask the question of how many bridesmaids and groomsmen they should have at their wedding. The unwritten rules call for an equal number so that they can be paired, and should include a matron of honor and a best man, who are responsible for organizing the bridal shower and the stag party. These rules are not set in stone; any number of groomsmen and bridesmaids may be used and do not necessarily have to be matched in pairs as long as the bride and groom are comfortable with their choices.

In a traditional Christian church wedding, the groom, best man, and minister enter through a side door and wait for the bride to walk down the aisle on her father's arm. The groomsmen may either follow this tradition or escort the bridesmaids down the aisle preceding the maid of honor and the bride with her father. At traditional Jewish weddings, the groomsmen enter the temple at the head of the procession, followed by the best man and then the groom and his parents. The bridesmaids follow, then the maid of honor, and the bride enters last with her parents.

After the wedding ceremony, the bridesmaids and groomsmen exit the church first, paired with one another. They in turn are followed by the maid of honor paired with the best man, and then the bride and groom. In a wedding with an uneven number of male and female attendants, some same-sex pairs may be planned. While pictures are taken of the bride and groom and the guests throw confetti over them, the groomsmen and bridesmaids separate from the group and assist any guests who do not know how to get to the reception.

The groomsmen and bridesmaids should know before the wedding with whom they are to be paired, and practice at the rehearsal if all are able to attend. No rules exist for this matter, but the maid of honor generally will be paired with the best man. Married, engaged or dating couples are usually paired with one another, and other members are often paired according to height. The tallest bridesmaid is paired with the tallest groomsman and all the pairings are matched closely according to their height, including same-sex pairings.