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Answer: The following is an overview, regarding a second marriage for both chatan and kalla; some differences depend only on the kalla’s status. Some issues are affected by details or sensitivities, especially regarding issues that are less halachic or are the subject of machloket. A couple would discuss these matters with their rav/mesader kiddushin.
Tenaim – Many do not require a written tenaim document (see Hanisuin K’hilchatam 17:8).
Ketuba – A kalla who is not a betula receives half of what a betula receives for all three of a ketuba’s monetary elements (Shulchan Aruch, Even Haezer 67:1), and her status is referenced in certain places in the ketuba. Certain variables, especially not widely known facts (e.g., adoption, conversion), raise sensitivities during the public reading of the ketuba between the kiddushin and nisuim parts of the ceremony. The minhag of many is to not read the ketuba at a second time marriage (see opinions in Hanisuin K’hilchatam 17:24 and Nitei Gavriel 51:7).
Veil – The kalla going to her chupa with a veil is the sign of the wedding of a betula (Ketubot 15b), and the chatan covers her at "badekin." There is no badekin at a second marriage (see Rama, EH 55:1; Chelkat Mechokek 55:8), although some have the minhag that someone else puts the veil on her under the chupa (Nitei Gavriel 51:3).
Bemare Habazak - Rabbis Questions (657)
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Yichud (the couple’s seclusion) – According to many (see Rama, EH 55:1), the nisuin is accomplished by yichud. Therefore, it is especially important that the kalla not be a nidda, which would prevent full yichud (Nitei Gavriel 51:10).
Minhagim that are unchanged: chupa, breaking of the glass, ashes on the chatan’s head; kalla circling the chatan.
Level of Revelry: The recommendation of poskim and the minhag is that, while joyous, the second wedding is less elaborate, which can find expression in several areas – Many do not have a band (Aruch Hashulchan ibid.); the food is less extensive (Hanisuin K’hilchatam 17:29); the kalla’s dress is less elaborate (Nitei Gavriel 51:2). These are general guidelines, not halachic dictates.
Participation of the couple’s children – Many have the minhag that their children not take part in the chupa (Nitei Gavriel 51:9). The decision should be left to the children (if old enough), without the couple’s pressuring or reading into their decisions.
Sheva Berachot – Sheva Berachot under the chupa are standard, but at meals, it is complicated. The gemara (Ketubot 7a) says that for such a couple there are sheva berachot for only one day. There are three feasible and supported possibilities what one day means (see Rosh, Ketubot 1:13 and its analysis in Chelkat Mechokek 62:6 and Beit Shmuel 62:5): 1) the first meal; 2) any meal eaten the first day; 3) it must be both the first meal and on the first day. The main differences are: A. After a night wedding, can there be a party with the sheva berachot recited the next day? B. If the chupa takes place at the end of the day and the meal takes place at night, are there berachot at the end of the wedding meal? The general approach is that there is doubt in these test cases, and we do not make berachot in a case of doubt (Beit Shmuel ibid.). Therefore, it is best to time things wisely. The Pitchei Teshuva (ad loc. 10) and Aruch Hashulchan (EH 62:33) cite opinions that if the yichud is at night, then even if the chupa was before, they can recite sheva berachot at night. The Ezer Mikodesh (to EH 62:6) is unsure if this is correct. If the meal was well underway during the day, sheva berachot can be recited at its conclusion at night (Aruch Hashulchan ibid.; Hanisuin K’hilchatam 17:35).
Time together – The couple is supposed to spend happy time together, as opposed to going to work, for three days (Ketubot 7a). The kalla is able to allow the chatan to return to work early (Rama, EH 64:2).
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