Our Gemara on Amud Aleph references the custom in Judea (Mishna Kesuvos 1:5) of allowing the betrothed bride and groom to have a period of time to be alone together. (They are married through Kiddushin but have not yet completed nisuin.)

Rashi (“Chutz”) explains:

“That he be accustomed and playful with her, so they not be embarrassed of each other when they consummate on the wedding night.”

While this custom did not become widespread, perhaps due to the appearance of impropriety, its aims are worthy. There was a recognition by Chazal of the inherent psychological challenges of introducing sexual intimacy, under pressure, to a young couple.

Many religious women and some men suffer from wedding night trauma. To help rabbis, Kallah teachers and therapists appreciate the potential difficulties I often compare this to the following metaphor:

One of the two greatest cultural taboos in Judaism (aside from sexuality) are the consumption of pork and the consumption of chometz (leavened bread) on Passover.  I ask what might it be like, if all of the sudden, their most revered rabbi instructed them that it was a mitzvah to consume a ham sandwich on rye bread at the Passover Seder!  After years of conditioning, no matter how convincing their rabbi might be, how could any devout Jew not gag on his food.  So too, in regard to sexuality, which has been forbidden with the strongest taboos, a young couple is now told it is a most important and holy mitzvah!

While I doubt there ever will be a time in Judaism where this odd custom will be followed, the spirit of the custom is valid.  It would seem to be a good idea, that engaged couples be allowed some process that will allow them to, as Rashi put it, “Be accustomed and playful, so they not be embarrassed of each other when they consummate on the wedding night.”  If in Judea they were allowed to be alone together, which we cannot allow for numerous reasons including the fact that there is no Kiddushin in modern engagements, we still see that the regular standard of modesty was loosened for the worthwhile aim of avoiding excessive anxiety and distress.  It is up to each rabbinic advisor and parents to consider what might be appropriate, given the emotional and developmental needs of each couple.

Translations Courtesy of Sefaria, except when, sometimes, I disagree with the translation

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