If a Jewish family suffers the loss of a family member right before a holiday, for example, Rosh Hashanah, is it appropriate to wish them L'Shana Tova? How should that be handled?

You ask a very good question that is quite sensitive, and it functions on both halachik (Jewish legal) as well as on the psychological and interpersonal levels.  Indeed, from a legal perspective we are prohibited from greeting mourners during their shiva period. Thus, one would think that wishing “L’shana Tova” would indeed be out of place to a mourner during that time. 

 

However, there is no way that the bereaved family will be in the midst of their shiva mourning period on Rosh Hashanah.  That is because shiva will, of necessity, either already be concluded or not yet be started.  The Shulchan Aruch states (Yoreh Deah 399:1) that if a funeral has taken place before a major Jewish holiday, the holiday ends the shiva with its onset.  So if the burial was even shortly before Rosh Hashanah, the moments of shiva before the holiday comprise the entirety of the shiva period.  And if the death was before Rosh Hashanah but the funeral has to be delayed until after the holiday for some reason, then shiva will not yet have started.  As such, there is no specific prohibition against greeting the mourner on Rosh Hashanah itself.

 

That said, there is still an interpersonal dimension that requires address.  Rav Soloveitchik pointed out that in addition to the formal mourning legislated by Jewish law that includes sitting shiva and wearing a torn short and sitting on a low chair, there exists concurrently the “informal mourning” that naturally comes from a person’s upset mindset.  Usually these two coincide, but when law cuts shiva short it doesn’t necessarily lessen in any way the deep pain and grief that the person is experiencing.

 

As a result, a standard holiday greeting may actually cause this person pain, making him or her feel as if everyone else is ignoring their loss. Saying nothing may also hurt, leaving the person feeling isolated and uncared for.  Acknowledging the loss in your greeting may offer a respectful way to approach this.  Perhaps most advisable would be to walk over to them and say “I can’t quite imagine how you are feeling right now, and I wish you a year of comfort, a better year than the one difficult one that just ended.  How are you managing?”