The 10 Best Stand-up Comics on Dating in the 21st Century

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The 10 Best Stand-up Comics on Dating in the 21st Century

Dating, by any other name, still smells as rank. Sure, in the sea of swipes and matches and messages and meet-ups, there’s the possibility of coming across a tangible spark, but the other 99% of the time there’s an endless parade of bots, dick pics, ghosting or the classic dick pics then ghosting.

Dating may not have ever been the most pleasurable of past times—“Hello, gentleman caller, please meet my parents. They will be supervising us in the parlor.”—but more than ever it has devolved into a tortuous experience that feels closer to a job interview for romance. Nowhere has the topic of dating—including being single or in a serious relationship—been more fully and honestly explored than in stand-up comedy. Comics speak from personal and observed experiences, and remind their listeners that, despite what your Instagram feed might suggest, it’s not all engagement rings and last minute tropical vacations. Their candid observations structured through humor make the entire process a little less tiresome. Here are ten stand-up comedians who offer a refreshing perspective on dating in the 21st century.

10. Sasheer Zamata

Zamata may have seen her star rise once she joined the cast of Saturday Night Live in the 2013-2014 season, but alone onstage and with a mic in hand, she’s a formidable voice bringing attention to the nuances of dating. Like many other comics on this list, Zamata’s stand-up isn’t all about her love life or relationships, but the moments she does focus on those subjects, she talks sincerely and oftentimes sarcastically about her more memorable experiences, especially when it comes to interracial dating.

9. Anthony Jeselnik

Jeselnik’s simmering disdain comes across in every word he articulates and the slower pace with which he tends to perform his sets. When he applies that style to relationships, he cuts to the heart of the bullshit that often surrounds human connections. If most comics aim for “biting” in terms of their commentary, Jeselnik wants more. His razor-edge perspective might strike some listeners as uncomfortable, but he unearths a truth that’s far more telling than most funny dating stories will ever communicate.

8. Naomi Ekperigin

Ekperigin’s material revolves around her engagement—and eventual marriage—to her “Jew boo,” but it’s the stories she tells about getting there that make her such a sharp-witted and necessary voice for anyone still “on the market.” When her diamond ring seems poised to put her at odds with her audience, she’s quick to shut them down with a blunt “Bitches, I earned this shit.” Seeing things from the vantage point of a successful relationship certainly strikes a different note than comics who are still single and able to commiserate with their audiences, but Ekperigin hasn’t lost her touch. If anything, she adds a distinct hilarity to the long search for a soul mate.

7. Bo Burnham

A musical comedian through and through, Burnham allows the fact that he plays piano onstage—in between calibrated and cleverly timed scenes—to punctuate his sarcasm so it lands with an even greater bite. When he trains his seething perspective on dating and relationships, it doesn’t come with a pretty façade. And that’s what audiences love about him. They eat up the persona he enacts onstage when anyone else might receive a slap for such opinions. Rather than go into anecdotes about his own experiences with dating, Burnham lays bare what people really should be doing to find that special someone.

6. Katherine Ryan

Ryan approaches dating from the wry perspective of a single mother, though her material isn’t always couched from such a specific approach. The Canadian-born and British-based version of a brutally honest Amy Schumer or Sarah Silverman, Ryan is willing to say anything. It’s that kind of perspicacity that has endeared her to young audiences in the United Kingdom and beyond. More than discussing the minefield of bad dates and dating annoyances, which come out throughout her sets, Ryan also opens up about her own shortcomings to underscore how it takes two to tango.

5. Mark Normand

Normand revels in upending the mundanities of any given situation. He often flips the script on his listeners in order to pinpoint the underlying fallacy involved. It’s an update on the classic “Men do this, women do that” routine. Case in point: Why can a woman interrupt his story at dinner to explain she prefers the strong silent type? As he points out, a man would come off looking sociopathic for a similar comment. Normand enjoys calling bullshit on numerous behaviors that make dating such a grind in the modern experience.

4. Aparna Nancherla

Many comedians like to entertain audiences with wild stories about the crazy characters they meet on a first date or the never-ending exasperations of their relationship, but Nancherla goes about things differently. While her material does contain awkward dating stories—which, coming from a comic known for her social anxiety, usually end hilariously—she also looks deep into the heart of what it means to be single. Nancherla revels in building twists and turns into her comedy, always playing with audience expectations and riffing on classic dating jokes with her own clever quirk.

3. Garfunkel and Oates

There’s talking about dating, and then there’s singing about dating. Musical comedians Garfunkel and Oates (aka Kate Micucci and Riki Lindhome) put a twist on the folk singers of yore with a series of songs aimed at less… innocent experiences. Fuck holding hands, these women tackle blowjobs, smug pregnant women and booty calls. All the while, their sweet demeanor belies their biting lyricism, and their plucky rhythms, courtesy of a guitar and ukulele, contrast the forthrightness of their topics. With hilarious honesty, the two add a melodic touch to the ways people get up close and personal nowadays.

2. Iliza Shlesinger

Shlesinger more than peels back the curtain on every idiosyncratic dating routine women go through in order to impress a guy—she practically burns it all down. People now know a lot more about the way women prepare for a date than their grandparents likely did, but Shlesinger isn’t content to stop there and play within familiar routines. With brutal honesty, she details the unspoken things women do. Like shaving their big toes. That kind of candor has quickly amassed her a loyal fanbase who know she will speak about things women once only whispered about among their friends and, more likely, to themselves.

1. Aziz Ansari

Ansari wrote the book, quite literally, on Modern Love, in 2015. He partnered with sociologist Eric Klinenberg to do a deep dive—both scientifically and anecdotally—into the dating phenomena he had witnessed firsthand as well as through friends. That book grew out of his stand-up, which focuses heavily on dating, relationships and the growing communication chasm in the digital age. Dating apps? Check. Ghosting? Check. Flakiness? Check. Ansari covers it all, much to listeners’ delight. By poring over the strange experience of dating in the 21st century, Ansari represents the wizened (and hilarious) voice of a generation.

Amanda Wicks is a freelance journalist specializing in comedy and music. Follow her on Twitter @aawicks.