You can’t get to the land of cool without first climbing cringe mountain.—Erica Mallett, New York Times.

Difficulty: High
Length: Decades
Out-and-Back or Loop: Never-ending Anxiety Loop

As dangerous as Everest and as technically demanding as K2, no discussion of the world’s most challenging peaks is complete without a mention of Cringe Mountain. But for those willing to undertake the rigorous climb, the rewards waiting at the summit are extraordinary.

Regardless of your desired route, advance planning is key for your journey. Be prepared for crowds on the Instagram face of the mountain to spike during holidays like Mother’s Day and Father’s Day. It’s also important to come properly outfitted for your ascent, as exposure on Cringe Mountain can be deadly. (Ankle socks, mom jeans, and a French tuck should be fine.)

The most popular and widely accessible entry point to Cringe is having been born in the eighties or nineties. The lower section of this trail is gentle and promises landscape features familiar to most millennials, including plenty of heckin’ puppers and doggos, the crying-laughing emoji, and adulting.

Eventually, this route intersects with the path from the Gen Z trailhead, which can present a steep learning curve for the millennial hiker. But not to worry—ironically using Gen Z slang you’ve read about online will only bring you closer to the apex of Cringe. Skibidi, indeed!

About a quarter mile past this intersection, you’ll encounter a stream. The water may be tempting, but be wary when confronting your reflection, especially without a filter. Self-awareness this early in the climb could easily wreck your chances of summiting.

As the incline picks up and you emerge from the tree line, you’ll find increasingly less protection from the harsh elements. Luckily, the Saddle of Ambivalence provides a good spot to take a break and wonder if making art or maintaining an online presence is even worth it. Beginners may want to call it a day here, accept that they are old, and simply stop downloading new social-media platforms.

There is no shame in turning around at the saddle. You do not want to be lost on Cringe Mountain after dark. The mountain sustains a diverse ecosystem of haters, many species of which are anonymous and therefore particularly vicious. If attacked, you’ll likely end up digging yourself deeper and deeper into a defensive hole, which will only sap your remaining energy for the ascent.

If you do choose to press on, expect rough terrain. You’re about to hit the most notoriously treacherous section of the trail, the jagged Ridgeline of Posting About Current Events. If you step too far in the direction of earnestness, you’re out of touch; if you’re too irreverent, you risk misreading the room. Only a few perilous inches separate Cringe and the Abyss of Tone-Deaf. When in doubt, follow other hikers’ leads.