Imagine yourself as a 27-year-old guy living with a grandmother who glimpsed you in bed with your lover last night. Pretty awkward, huh? Now imagine the same scenario but in an Arab country, with the person in your bed a man and your moderately conservative grandmother having thrown a fit. That's the mortifying night just experienced by Rasa, the beleaguered narrator/protagonist of Saleem Haddad's original and knowing debut novel, "Guapa."

Named for a gay-friendly bar that figures prominently in the story, which takes place in an unnamed Arab country, "Guapa" follows its main character as he muddles through the dread-filled day after the night from hell. Rasa relates the tale in the present tense, and includes extended flashbacks to his childhood in the same country as well as his college years in the United States.

Because of the previous night's fiasco, Rasa's boyfriend, Taymour, already conflicted about their relationship due to a fear of exposure, grows distant and noncommittal. Rasa begins to panic, trying to ascertain through increasingly frantic text messages whether they're still a couple. At first, this quest elicits our compassion and imbues the story with a sense of urgency. But when it is (belatedly) revealed that Rasa knows Taymour's wedding is tonight, and that he cynically helped facilitate the relationship with his bride so that they have a cover, we feel duped. Surely this wasn't the author's intention.

Haddad was born in Kuwait to an Iraqi-German mother and a Lebanese-Palestinian father, and today lives in London. His story's setting, meanwhile, evokes contemporary Damascus and the conflict over Syria. In one particularly affecting encounter, Rasa, who together with two friends has established a tiny translation company, is serving as interpreter for an American journalist. The journalist is interviewing a middle-aged Islamist couple whose 24-year-old son, Abdallah, went missing after attending an anti-regime protest.

As it happens, Rasa has just discovered that his bosom buddy Maj was arrested the night before at a cruising spot for gay men. "I want to tell Um Abdallah that my best friend is also being held by the regime for who he is, for who he wants to be, but I cannot find the words to do so," he agonizes, knowing that Abdallah's mother has no sympathy for his kind.

At its best, "Guapa" deftly captures the surrealism both of living a double life and navigating the hall of mirrors within which a quasi-totalitarian regime encloses society. As Maj, not only a flamboyant performer (in drag) at Guapa but an irrepressible social critic, puts it: "We're all alone, and everyone in this country is giving an Oscar-winning performance to try to belong. … The problem with you, Rasa, is that you want to integrate. But look around. There is nothing real to integrate into."

Rayyan Al-Shawaf is a writer and book critic in Lebanon.