How To Catch A Gen Z’er

A middle-aged man’s quest for young love

Vicki Tran
Slackjaw
3 min readSep 12, 2020

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Photo by Andrea Piacquadio on Pexels

Is your current dating pool aging out? Are you having trouble keeping up with all your fake social media profiles? Are you tired of translating your messages with Urban Dictionary? Hi, I’m Walter, and I’m here to share my struggles with dating Generation Z as a middle-aged man. If you’re anything like me, you stopped finding millennials attractive as soon as they started getting 401ks. I was once your leading expert in playing the field, but as soon as I turned my attention to 18+ Gen Z, they turned on me. After challenging me to show my face after two texts, doubting my modeling career, and mocking my air-brushed abs, I feared no one would ever get to know me or my My Little Pony collection.

When you search “How to Target Gen Z,” the hot button articles only explain how to work with Gen Z. But where are the tips for attracting Gen Z?! After eight seasons on MTV, we knew catfishing worked with millennials. But how are we going to hook, line, and kink Gen Z? Okay, Boomer. Sit down and listen up.

1. Learn the slang before you can smang

The days of asking “A/S/L?” in an AOL chatroom are over, because guess what? Zoomers don’t even know what AOL stands for. Age is but a number, sex is genderless, and the location is the world wide web. I know, I’m shook too. Also, the new kids on the block are a vocal generation. They’re well-informed because they can form an opinion just by reading a headline. If you can’t advocate for climate change or justify who you’re voting for in an election, they can sniff that shit out like Gwyneth Paltrow’s coochie candle.

2. Expand your outlook beyond “Facebook stalking” to the general term “internet stalking”

If you don’t post, you don’t exist. Kids these days are on multiple social platforms, so sign up today before all the apps are banned. Apparently you can’t upload two random shitty photos on The Facebook and expect results anymore. And if you have less than 100 followers, you’re basically a robot (BOT BYE). Welcome to the big leagues where learning Tik Tok dances will become a habit, a state of mind, and a lifestyle.

3. Dress for the prey you want, not the prey you have

It’s time to hang up our “Namaste in Bed” shirts and hit the thrift shops. Do you own anything tie-dye? Do you own a bucket hat? Do you own a tie-dyed bucket hat? Understanding their clothes means you’re one step closer to getting them out of their clothes. But that shit better be sustainably sourced, or they’ll cancel you.

4. A selfie’s worth 1,000 words

You’re going to need more than a slimy DM to entice those Gen Z kids. And unlike before, when you could avoid showing your face, Gen Z thrives on visual content. So treat yo self to an iPhone 4 and learn your goddamn angles.

5. Appeal to their entrepreneurial spirit, since you too are seeking services from youngsters

If you don’t have a side hustle, you don’t have a shot. Work on defining your brand and what you offer. Am I a…

Fitness coach?

Tiny home decorator?

Dog influencer?

Also, I’m pleased to say the free candy tactic* is BACK, baby. Offering discounts, rewards, freemium on your “services” will have them knocking at your door.

*Disclaimer — This might not actually be a generational trend, but they are some thrifty mofos.

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Vicki Tran
Slackjaw

Product Manager, Humor Writer, and Former College Mascot (HokieBird). Contributor to Slackjaw, The Belladonna, The Haven, and Funny-ish. For more: @itsvickitran