I like that his sound has matured and softened, to an extent. It gives it more longevity as his fan base (like me) ages, I'm 36 now. I was never really living like The Weeknd in terms of endless casual sex and messy relationships/hook ups, I am a little too focused and sober for that, ( but similar in it's own way.). So, his music was never that personal for me, in terms of actually relating to Vegas hookup nights, but the feel was deeply personal, of a little isolation, late nights, and feeling apart from the world, and even your own relationships.
At age 16/17 I was 100% doing a lot of cocaine, in hotel rooms, with my homies, with girls my age, and sometimes older escorts, money falling out of my pockets, as quickly as the valium pills, blue, smeared across the counter on the bathroom counter, blood on the hotel towels watching girls strip down in the harsh lighting. So, I get the life. I lived it really young.
at 36, I don't really want to revel in the temporary pleasures and often messiness of that shyt, so I like that his music matches that, instead of doubling down on the Trilogy 10 years later. And still throws the references to a more than slightly nomadic, at times a little depressive, or nihilistic lifestyle.
Less Than Zero was my favorite book in high school, for example, and now I find that writer a little on the nose, and not nearly as talented as the author of Bright Lights Big City, both 80's classics about excess, relationships, cocaine. Hence, the Weeknd's nod to the Bret Easton Ellis novel.