Cup Match is upon us once again.

This is, far and away, Bermuda's favourite holiday, a much needed two-day break in the high heat of summer.

And while most of the emphasis is on spending time with friends and family at the Game, on the beach or water, or just cooling out at home, it's a good time to reflect as well.

Cup Match was established, as Glenn Fubler explains so well on this page, by the Friendly Societies to mark the anniversary of Emancipation Day on August 1, 1834.

That anniversary remains inextricably linked with the holiday, and rightly, this aspect of the holiday has received greater attention in recent years.

That's because, in spite of the enormous strides that have been made since the bonds of segregation were broken in the late 1950s and early 1960s, Bermuda's races remain divided, and much of this has to do with the legacy of slavery and segregation.

In part, this is because of the wealth gap that still exists between blacks and whites in the community, and in part it is because the black and white experiences remain quite different and these differences in perceptions can be quite jarring when they come to the surface. The recent debate over the lack of white attendance at the funeral of Dame Lois Browne Evans gave some indication of that, both in terms of the lack of understanding on the part of many whites of what Dame Lois meant to the black community, but also how white and black Bermudians tend to view and attend funerals in quite different ways.

Working out how to tackle Bermuda's racial problems, especially in an era of heightened political tension in which race is never far from the surface, is challenging.

But there can be no doubt that continued dialogue between the races, both formally and informally, is essential to bridge the communication gap, and there have been some eloquent discussions about that in recent letters to the Editor.

But it has to be a genuine two-way discussion and that still is not the case. Whites need to join the discussion and give real thought to their place in society. And they need to honestly put themselves in the shoes of black Bermudians to consider whether they would enjoy the same privileges that many ¿ although not all ¿ do in today's Bermuda.

If they consider that question honestly, then they ought at least to recognise that much more needs to be done to level the playing field so that all Bermudians have an honest chance at the good life.

At the same time, there is a tendency for some black Bermudians to "feed the inner victim", which can be as much of a block to personal emancipation from the bonds of the past as any genuine racism or discrimination that still exists today.

Continued dialogue between the races, both formally and informally, is essential to bridge the communication gap. This has to include serious discussion about how to ensure opportunities are equal between blacks and whites.

It is also true that this dialogue may well result in some discomfort, for whites in particular. But confrontation, and there have been examples of this recently, is rarely the answer, since it tends to put people of both races into defensive positions from which they are unwilling to dislodge themselves.

Cup Match, when people from all of Bermuda's diverse groups come together, is a good time to reflect on these questions.