Gender deconstruction, fraught feminism and the perils of hook-up culture: George Bernard Shaw’s comedy of manners, penned in 1893, shows we haven’t come as far as we might think. It’s a point rammed home by Paul Miller’s choice of modern dress, but this otherwise pleasantly conventional production cushions its provocations, with the real challenge coming from a near-three-hour running time.

Generation Y are worriers. There’s certainly plenty to fuel that angst, from mounting debts, employment uncertainty and the ever-worsening housing crisis to international conflict and terrorism – as explored by a slew of recent articles (and the occasional “How anxious are you, doomed millennial?” quiz). Brad Birch’s new 80-minute play occasionally wanders into that thinkpiece territory, but in the main, he and director Mel Hillyard have found a vividly theatrical form for this modern malaise.

I’m still pondering the title of Chris Urch’s new play. On the surface it’s clear enough: The Rolling Stone is a weekly newspaper in Uganda that has been notorious for pursuing that country’s anti-gay agenda. In particular, at the beginning of the decade, it started a campaign of publishing the photographs and addresses of those it believed to be homosexual.

Over the past quarter century the reputation of toff playwright Terence Rattigan has been restored, mainly by strong stagings of his classic dramas, such as Deep Blue Sea. But his first smash hit, French Without Tears, has been the unicorn of his output – often talked about, often mentioned, often remembered, but never actually seen.

Can you peg a whole play on a decent twist? When We Were Women’s narrative tease pays off interestingly, but takes a hell of a long time getting there. It leaves little space to explore the ramifications of an intriguing revelation, a frustration amplified by the constant chronological cross-cutting in this revived Sharman Macdonald work, first seen at the National in 1988.

Mustapha Matura's 1974 play is a celebration of liberation, both social and political, and a sly warning about the possible pitfalls of sudden freedom. Mas (or Masquerade) is the Trinidadian version of Carnival, an exotic mixture of Christian and African tradition played out just before Lent. It provides an opportunity to adopt a different persona, to drink to excess and to behave in ways unacceptable at any other time.

The Orange Tree’s renaissance continues with this searing piece from playwright of the moment Alice Birch, who will shortly follow up last year’s subversive Revolt. She Said. Revolt Again with an interrogation of the porn industry for Rufus Norris’s debut National season. Her fearlessness is also in evidence in deceptive early work Little Light, an initially typical domestic drama that furiously erupts in a bruising, bravura 90 minutes.

Are there any real taboos left? I mean, there have been scores of plays about incest, about abuse and about paedophilia. Have all proverbial stones been turned over? According to Deborah Bruce, a director turned playwright, there is one situation that still troubles people, especially women: it is mothers who leave their children. Although this is a staple of women’s magazines, there have been few plays about the subject. So Bruce’s new drama is welcome — and it comes with the always watchable Helen Baxendale as its star.

Sam Walters, Britain's longest-serving artistic director of a theatre (43 years!), looks to the past as well as the future with his Orange Tree swansong. This varied festival features nine plays and six world premieres across two programmes, all of them staged by returning graduates of the Richmond venue's trainee director scheme. The diligent Programme One viewer will spot a number of recurring subjects, including science teachers and astrophysicists, the resurfacing in adulthood of childhood dynamics, and constant grappling with faith and mortality.

In French, when you want to end a digression and get a conversation back on point, you say "revenons à nos moutons". It's a commonly used idiom, meaning literally "let's get back to our sheep", the sheep representing the  actual subject under discussion. It also offers a way of looking at David Mamet's one-act play Squirrels, too, for no matter how far away their flights of imagination take them, the characters will always find their way back to their original theme, with a little help from an improbable animal – a squirrel, not a sheep, but you get the idea.