I'm rereading Infinite Jest with my wife. Her first time, and it's fascinating watching her put the world together. This is a book that's written to be talked about.
That's fair; David Foster Wallace isn't lighthearted. My wife was nervous about getting into DFW too - she studied Tense Present in undergrad and knew about the suicide and depressive substance abuse - so I started her on a BIWHM audiobook while we were on a flight 2 weeks ago. She got a taste of some of the weirder character biographies and DFW's metafictional style, which intrigued her. I think the most challenging short from that series is #6 ("soft" subscription paywall, couldn't find a .pdf). Then I asked her to read A Supposedly Fun Thing I'll Never Do Again, which might be his funniest short piece but still hits with the hallmark agoraphobic/dissociative anxiety that's in all his stuff. Thing is, DFW perceived broken-up types. He wrote those characters unnervingly well, and it feels like exposure if you self-identify as much as he did - makes it difficult to extricate. Take care of yourself. Glad to hear you're coming out of it rather than heading in.
I don't think Infinite Jest is itself depressing, but you'll want to avoid some of the books that came after. After reading Oblivion I didn't feel surprised that he killed himself. From the wiki:In general, Marshall Boswell claimed that this was Wallace's "bleakest" work of fiction. In Oblivion, he "uncharacteristically" provides "no way out" of solipsism and loneliness. Boswell further suggested that the collection "repeatedly undermines many of the techniques for alleviation" from loneliness, like communicating through language, that Wallace presented in Infinite Jest. "Oblivion," he writes, "remains unique in Wallace's oeuvre in its unrelenting pessimism."[26]
My favorite moment of an otherwise thoroughly mediocre film came when the protagonist of Josh Radnor's Liberal Arts confronted a college kid in hospital after a suicide attempt. (Paraphrasing here:) Jesse: That's it, I'm taking you off the postmodernists. Dean: What? Why? Jesse: DFW is a great writer, but he's also great at reminding us how shitty and fucked up the world is. You've got enough of that. Here, go read the Romantics.