Life isn’t always a straightforward, leisurely stroll. Sometimes we stumble, sometimes we find ourselves in uncomfortable and embarrassing situations, sometimes our relationships flounder. Some seek to smooth over such blemishes—Isaac Oliver, however, is not such a person. In Intimacy Idiot, his debut collection of essays, Oliver celebrates some of his most outlandish sexual escapades, most traumatic travel experiences, and his unrequited, irrational love for strangers on the subway. The material breathes with sharp honesty and boasts an assured authorial voice, but it went through a few stages before reaching this final incarnation.

“I had a blog that I wrote for a few years, compiling things from living around the city, and a friend of mine said I should do a live evening with actors. Kind of like a gay Prairie Home Companion, with me off to the side narrating,” Oliver recalls. After almost a year of those performances, the artistic director at Ars Nova told Oliver he should be performing solo. “You have a voice and you have a presence, and I think you should just completely own the material.’ And I said, ‘Ok, but you have to direct it.’ ”

First performed two years ago, Intimacy Idiot developed into a regular show. “It’s a bit of a hybrid evening,” Oliver explains, “that's sort of half going to hear an author read, and half—it's not really stand-up comedy because I'm not much of a stander, I like to sit. So it's like sit-down comedy. We try to give it sort of a theatrical polish and present a thoughtfully arranged arc of pieces throughout the evening.”

So after first adapting the blog pieces to be performed, Oliver went back and re-adapted the pieces to be read. However, he was able to maintain some of his theatrical flair when it came to recording the audiobook. “That was sort of an out-of-body experience, because you're literally reading it in a vacuum. The nice thing about reading them live is that you have an audience who's laughing—and they're not laughing at you, they're really in a sense laughing with you, because I'm telling jokes, or I'm telling the story because I think it's funny. It may be at my own expense, but I'm in control of the story, I'm in control of the joke, so I'm a little protected in that sense. But,” he adds, pausing briefly, “there's something about reading the audiobook, going straight through, not having an audience, being in this soundproof silent space… I found myself relieving some of the encounters a little more vividly than I would have liked.”

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Between choking on a dusty dildo during Skype-sex and spilling a full glass of red wine all over his date (he describes it dripping from the guy’s glasses), one almost gets the sense that Oliver is on the hunt for awkward intimacies. “I really do try to experience people as people first and not potential characters,” he says. “That's not really how I go through the day, because it changes the way you interact with your life. The only time when I was really like, ‘Oh God, this is going to be good’ was with the guy who turned out to be a Furry.” A Furry, for those unaware, is someone who dresses up as an animal and socializes (not always sexually, but sometimes sexually) Oliver_cover2 with other Furries. “The minute he left I just grabbed my notebook and wrote down as many things as I could remember. But that's really the only instance where I thought in the moment, ‘Oh this is a story.’ ”

While not every story is about sex, many of them that deal with it stand out as particularly memorable, something his parents took notice of early on. “I hadn't told them about my blog, but I'm an idiot, and I put my full name in one entry. So my dad was just Googling things at one point and found it. They read the blog for a full year before they told me. Actually, I think that’s kind of incredible, because by the time they told me, it wasn't confrontation. It was sort of a measured thing where they said, ‘You know, we found your blog, we've been reading it for a year. You know, some of the pieces make us just sort of nervous or uncomfortable, it's a bit too much information for us. But, on the whole, we love reading it, we feel closer to you, we like knowing about you.’ The sexual pieces, my mom admitted, she’d skip over,” Oliver adds with a laugh. “But because they'd already been reading it, and read some pretty intense things, I didn't feel censored. So I kept writing and I would just put a little disclaimer, ‘Hi mom and dad, you might want to skip this one. Love you, see you at Thanksgiving.”

“They come to most of my shows,” he continues. “They get a little drink beforehand, which I think helps. My mom will have a mudslide or two and heckle me from the audience. They're very supportive. But there is sort of a caution. Every now and then, they will have a check-in with me and be like, ‘Are you being safe? Are you also looking to date people?’ ”

Does Oliver feel that sharing so much of himself so publicly has affected his relationships? “Well,” he says with characteristic deadpan humor, “that would require me having some. But, yeah, there have been a couple dates I have gone on, one recently, where you’re talking about what you do and I say I’m a writer. ‘Oh what do you write?’ Oh, I'm working on a book that's coming out in June. ‘What's it called?’ A pause and then, Intimacy Idiot. And he just stared blankly. It's just, it's not a great way to start out a date,” he says laughing. “I should probably come up with a fake title. Or I could spin it. I could be like, ‘But now let's write the sequel, No Longer an Idiot.’ ”

James McDonald is a British-trained historian and a New York-based writer. Follow him on Twitter.