A woman's Virgin Night is an especially important time in their lives and if it is not done with someone they can trust, it can be one of the most dangerous times as well. There is a chance that when the hymen is broken, there is a chance that the woman's inner web can be broken as well. If the Virgin Night is not done with care the power of the man might overwhelm the woman and cause them to shatter their inner web, or chalice, and become broken. If a woman is raped prior to their Virgin Night, the chances of them being broken goes up.
Virgin Nights do not usually happen with someone because of love, though that does happen occasionally. It is very important for a woman to undergo their Virgin Nights once they reach the age of maturity since the longer they wait means that the window for being broken gets longer. It is typically arranged by the young woman's family so that they know that it will happen with someone that they trust. This person can be of any age and it is thought to be an honor to see someone through their Virgin Night.
If you wish to break someone, then the best time to rape them would be prior to their Virgin Night. A male can roughly break the hymen and force their way past her barriers in the attempts to shatter her mind. The woman usually retreats into herself at this point and has to be very strong not to descend so far and so fast that they can accidentally break their own web.
The darkness of the Jewels does not really matter at this point and a lighter Jeweled male can still manage to break a dark Jeweled female. However, if the female has a dark enough Jewel, they can descend to a point where the male cannot follow and maybe protect herself from being broken. This takes a strong female though to manage to keep her wits about her and protect herself while this is happening and it is a strength that has nothing to do with Jewel strength.