There’s a moment in Ali Wong’s latest Netflix comedy special Single Lady where she’s talking about her expectations regarding the first date; she expects the guy to pay. “I know this sounds crazy because I’m a millionaire,” Wong says casually, before adding that this is a big deal for her because her ideal man must demonstrate that he understands “basic investment strategy”. “If you have faith in your product and it performs well on the market and stays up, that money will come back to you!”

That last line works not because of the sexual innuendo but because of Wong’s playful engagement with the idea of money as a dealmaker/breaker when it comes to romance. Sadly, this is one of the only times during the special that Wong truly confronts the reality of her own financial and societal status. Because of this, Single Lady is merely good, whereas her earlier specials like Baby Cobra (2016) and Hard Knock Wife (2018) were downright brilliant.

Single Lady is Wong’s first special since her very public divorce, something that “sent a Bat-signal to every potentially interested man, letting them know I’m suddenly available”. Through the 60-odd minutes of the show, Wong attempts to reverse the ‘sad, middle-aged divorced mom’ stereotype. She does so by chronicling the men who came after the divorce—a conventionally attractive but seemingly vacuous 25-year-old, a 60-year-old former pro surfer who lies about his age, the older admirer who woos her with elaborate, expensive flower arrangements sent to hotel rooms while she’s on tour.

Wong’s method is simple and somewhat repetitive. She makes fun of these men in a way that reveals the gendered nature of groupthink and societal acceptance. A male friend dating a much younger woman is skewered by Wong and their circle-of-friends. “You bring this hot, unfunny dummy to dinner? All the women of substance at the table are now mad at you because they have to babysit this bitch!”

The 25-year-old hot-but-clueless fling thinks that when Wong wants to go to a museum, it’s “cool, ‘cos I’m down to see dinosaurs”. The 60-year-old boyfriend “screams violently” upon orgasm and then collapses on top of her. “You feel like you’ve just pulled the wrong piece out of a Jenga tower.”

All of these jokes are funny in the moment, but together they don’t quite add up to the coherent story we’re used to from Wong. You can see why she chose this method for Single Lady. The idea is to present an elaborate parody of ‘dudes rock’ humour, where sex is more than anything else a power game, a matter of bragging rights, a way of reinforcing hierarchies. “I’m no longer trying to trap a man,” Wong says, acknowledging her previous joke from Baby Cobra. “I’m trying to catch a concussion! I don’t care how many brain cells you have. I don’t care how you pronounce hors d’oeuvres. I just want you to have a huge boner for me all the time.”  

In terms of power, money and name recognition, Wong is now looking a lot like the middle-aged male white celebrities she’s trying to satirise

The problem is, Wong’s case for liberatory mid-life divorce (“look how much fun I’m having!”) looks more like an endorsement for mid-life windfalls. When her 25-year-old fling’s intellectual deficiencies are made clear, she jokes about wanting to tell him to his face, “Okay, I’m gonna fuck you like five or six times more”. She also jokes about buying expensive stuff for this broke young man.

The routine is a comment on how if the roles were reversed, nobody would bat an eyelid at a successful male celebrity ‘using’ and then summarily dismissing a young woman like that. It’s ‘reverse humour’ at a very first-degree level. And it’s much less impactful now that Wong’s career has skyrocketed over the last decade, in both comedy and mainstream Hollywood. In terms of power, money and name recognition, Wong is now looking a lot like the middle-aged male white celebrities she’s trying to satirise here—and that’s why this routine stands on shaky ground.

There’s a parallel to be drawn here with the diminishing comedic returns of Chris Rock and Dave Chappelle. Both of these guys made their name with some very funny insights about the intersection of race and class in America. But as their stars rose and they became worth hundreds of millions of dollars, those same jokes rang a little bit hollow.   

At the beginning of Single Lady, Wong says that her divorce left her feeling “embarrassed and ashamed” but she then does not touch upon this at all, even in passing. In the special’s last couple of minutes, she abandons her sexual-escapades structure and reveals that the man who bombarded her non-stop with flowers was, in fact, her current boyfriend, the actor and comedian Bill Hader.

It feels like an oddly safe, even pandering choice at the storytelling level, especially after you have just spent an hour regaling your audience about the liberation offered by strings-free dating. Wong remains a more than capable performer and a lot of the standalone jokes here are reminders of her writing skills. But longtime fans will be disappointed with Single Lady’s glaring lack of ambition, especially when compared to her previous efforts.