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Elder Millennial’s self-deprecation helped me confront the pain of modern dating

As Iliza Shlesinger paces across the stage in her Elder Millennial Netflix stand-up special, sporting an all-black outfit, red lipstick and dramatic high ponytail, she seems to radiate confidence. Thirty seconds in, her voice drops into a shaky register and her shoulders hunch, she quips, “Gather around the Snapchat, children.”

Iliza is 35, born in the first three years of the millennial generation. She’s been active on the comedy scene since 2007, first gaining recognition by winning MySpace’s So You Think You’re Funny contest. Since then, she’s had four comedy specials taped, released, and promoted by Netflix. Her satire continues to receive press and draw new audiences with its discourse centered around gender, relationships and the societal norms of our generation.

Part of her great scenic presence may very well stem from Shesinger’s ability to be openly weird: she regularly launches into high-pitched shrieks and warbling character voices, taking on the personas of a “party goblin” and witch as well as various species of birds, and of course, dudes. 

As an “elder millennial,” Iliza has lived through the generation’s unique trends, habits and challenges, and puts this knowledge on sharp display in her set. This experience comes across most clearly in Shlesinger’s stories about millennial dating. As someone half-heartedly swiping on Bumble while I watched the special, these jokes elicited laughs, but also resonated in a more emotional way.

In Elder Millennial, Iliza appears to close the chapter on these years of strange, undefined relationships, announcing her engagement: “I’m going to be 35 when I get married,” she says. “And if there was a secret, I would’ve f*cking used it.”

This speaks to a societally engrained urge to get married, one that Iliza’s comedy grapples with. Her special inhabits the duality of today’s dating and relationship dynamics, one in which women are often expected to be fiercely independent and not want a relationship, yet pressured by the idea that they will eventually “settle down.”

In other words, society tells us that of course relationships should represent some sort of sacred goal. After all, it would be sad to be single forever. Yet efforts to find a partner become labeled as “desperate.” Rather, women should somehow fall into a relationship, like a vintage-clad Zooey Deschanel in a rom-com.

In Elder Millennial, Shlesinger pokes fun at the “desperate, serial dater” stereotype. She describes her and her friends dressing in strappy heels and crop tops to go out, sipping their drinks and waiting for men to approach like “gazelles at a watering hole.” She jokes that when she goes to Trader Joe’s, women spot her engagement ring and bombard her, “looking for the secret to finding a suitor.”

“I don’t like to tell people how we met,” Iliza responds. “We met on a dating app.”

To me, this shows that women often feel embarrassed to be seeking out relationships, or to admit that they want one. Similarly, when I admit that I’ve used dating apps, I quickly follow up with a list of excuses: I wouldn’t date a coworker, I don’t want to meet someone in a bar, Guys who already know me think I’m intimidating. Taking agency over one’s own love life, it appears, is only permissible if it’s a last resort, if no other option remains.

Like Iliza, I’ve often joked about my inability to navigate dating and develop a happy, healthy relationship. This dark humor emerged most recently at my cousin’s wedding, where — after three glasses of wine — I said, “I probably won’t get married until I’m 60. Whoever’s still alive is who gets to be in the wedding party.”

That same night, I text a guy I’m interested in and who I’ve been dating on-and-off. Recently, it feels like we’re at a stand still, and my friends have advised me to be assertive.

I ask him to hang out sometime later in the week, and he never responds. Maybe I’ve lifted the veil too much. I’ve shown him that I actually want a relationship, and the desperation is revolting. Maybe we were never really dating at all.

“It’s like single women can feel the vibrations of my ring,” Shlesinger says in her newest Netflix special.

Looking at my cousin’s perfect diamond, this doesn’t seem like much of an exaggeration.

In Elder Millennial, Shlesinger presents a common, sparkling dream — one that hurts when young, feminist women recognize it in themselves.

By Kara Lewis

Kara Lewis is a journalist and poet living in Kansas City, Missouri. She can usually be found talking loudly about feminism over a plate of nachos, making a Gilmore Girls reference no one caught, or listening to a thought-provoking podcast. Follow her on Twitter for okay writing and extraordinary gifs.