No one makes partying sound less fun than Drake. For the Young Money cash crop, hitting the club means fierce stares from competitors, vapid advances from gold-diggers, and woozy blackouts from getting too crossfaded. Since his major label debut, Drizzy has made art of the indefinable grey between the euphoric climax of a night on the town and the awkward pregames and hasty comedowns that surround it on either side. Even more subtly, Drake employs this bell curve as a metaphor for the broader highs and lows of fame, wealth, and love. A recent trio of leaks from his upcoming sophomore effort Take Care find Drake musing on the ironies of contemporary young adulthood: an insatiable materialism coupled with a dismal global economy, a nihilist rebellion against growing old while demanding respect from elders and peers, and a difficulty expressing love amid a romanticizing of casual sex. Drake is widely criticized by rap stalwarts for being too emotional, but the feelings he’s engaging with aren’t just his own—they’re the swirling conflicts that a generation of “emerging adults” are facing every day, and are trying to forget about every night.

The pregame starts with “Dreams Money Can Buy.” Released to much fanfare in mid May, “Dreams” is Drake’s take on “Mo’ Money, Mo’ Problems,”—a brooding lament on being too busy to drive a new car, getting a girlfriend with priors through French customs, and above all else, wanting more money. But at its root are the difficulties that his wealth can’t fix: longing to be loved, ceaseless competition, and loss of faith in his heroes. The song is anchored by a looped sample of Jai Paul crooning “Don’t fuck with me” in falsetto, an ambiguous, unspecified statement that could be a confrontational demand, a fearful plea, or a self-loathing warning. It’s hard to know, particularly because Drake himself isn’t very sure. By the song’s end it’s hard to tell whether Drake was happy, sad, angry, or any mix of the three—he’s just on his way, and hopes there’s some good pussy waiting when he gets there.

Most striking of the Take Care leaks is “Trust Issues,” a slow-burning trance that reeks strongly of his good buddy (buddies?) The Weeknd. “Issues” finds Drake recontextualizing his hook on DJ Khaled’s “I’m On One”: instead of the triumphant declaration of youthful rebellion at the bottom of a shot glass that we meet on Khaled’s track, “Trust Issues” fills the quatrain with insecurity and a tangible sense of despair—it sounds like he’s trying to convince himself as much as he is the listener. During his rapped verse, he subtly bounces between proud braggadocio and emotional prodding, never seeming quite sure of which is right. The most jolting shift occurs between the half-whispered “if y’all what I created than I hate myself,” and the quick concession “but still, let them girls in”—one can almost feel him shake from his inner thoughts and return to the party he’s hosting. He doesn’t feel secure enough to commit to a girl that may be the one, and his only escape is to drink more and keep the party going: confiding in her and pushing her away all at once. As “Issues” slurs to a close, the ambiguity that hangs is whether the narrator in fact can’t trust others, or himself.

“Marvin’s Room” is the most conceptual of the leaks, with Drake recreating a desperate phone call to an ex after drinking too much Rosé at a party. Despite the droves of girls at his disposal (and having sex four times that week), he is fixated with the one he cannot have. Drake paints an all too common picture of many young people’s sexual frustrations—rampant promiscuity rests on the idea that the next girl (or guy) will always be better than the last, a cycle that leaves one unfulfilled and emotionally drained. His sadness, then, doesn’t necessarily come from missing his ex girl, but more the idea that she may actually be happy without him, and that tomorrow night’s romp will not fill the void that her moving on has created. He never expresses interest in continuing a relationship, he just needs “someone to put this weight on,” someone that wants to be there for him.

Through his three latest tracks, Drake creates a story ark that conveys a dark truth about the club: it isn’t a very happy place. It harbors insecurity, confrontation, and a constant dissatisfaction and assurance that someone, somewhere else is having a better time. In a recent interview with The Fader, Drake noted that his album is for the “kids driving around the city, reflecting on life.” Judging by the themes he’s been exploring, it isn’t hard to imagine what kind of lives those kids are living. These are the songs of sadness with a smile, colored with shades of purple and blue as dark as a V.I.P section, and with boundaries just as difficult to parse.