Woody Allen's latest film certainly proves one thing, over and over again: It's not interesting to watch an ensemble drama about imbeciles. You can throw great actors at the script, make sure your lighting team is punctual and professional, but if the end product celebrates the foibles of idiots, what are you left with? You're left with nothing. The acting is clearly top-notch, but there isn't one character to emotionally invest in, not one person who comes on screen that makes you think, "Ah, what will this wild card get up to next?" In making a film about "real life" Woody Allen has stocked his film with the unremarkable and irredeemable. Fiddlesticks.
Naomi Watts is unhappily married to Josh Brolin. She's the assistant to Antonio Banderas, who runs an art gallery, who is also unhappily married. Watts' mother, played by Gemma Jones, is recently separated from her husband, played by Anthony Hopkins. They were unhappily married. Freida Pinto lives across the street from Brolin and Watts, and she's engaged ... but she might be having problems in her relationship. That's four examples of co-mingling, none of which are happy. But wait! If you wait long enough, at least three more relationships within the aforementioned groupings will go sour. Something to look forward to!
The issue here is not that stories of emotional trauma can't be interesting or well done, the issue here is that you want to see these people in psychic pain, because they all make all the wrong choices. To cheer for these rubes would be to cheer for the fool who runs onto the field at a sporting event. He just wants attention, only he doesn't know how to get it, or the appropriate format to get it in. That's every single person in this movie, so how can you pull for them? To root for these clueless folk is a bridge too far for even the most empathetic audience member.
In fairness, there a few moments of wry humor presented in You Will Meet a Tall Dark Stranger, and credit must be given on that front. The film seems like Arrested Development gone dramatic, up to and including a central character saying, "I've made a huge mistake." The acting is technically proficient; Watts, Brolin, and Lucy Punch do their absolute best with middling material. Sadly, that's not enough to save the day. At 98 minutes, it's too long by half, as we don't need more than a few minutes in the company of a person flailing about, wildly gesticulating, and forgetting to intake oxygen to know we should call for help. Then we should get back to living our lives.