8 awkward signs a boomer is trying too hard to “blend in” with younger generations

Every generation eventually faces that moment when they realize they’re no longer the youth. For boomers, that moment happened somewhere around 1985, but some are still fighting it with the determination of someone trying to return something at Costco without a receipt. The result isn’t bridging the generation gap—it’s creating a kind of performance art that makes everyone uncomfortable, especially their own kids.

The tragedy isn’t aging. It’s the desperate scramble to prove you’re not aging, using tools and references that actually highlight exactly how out of touch you’ve become.

1. Using internet slang like they’re reading from flashcards

“That’s so lit, fam!” they say, with the confidence of someone who just learned these words from a BuzzFeed article titled “25 Terms Millennials Use.” The problem isn’t just that they’re using slang—it’s that they’re using it like someone speaking a foreign language from a phrasebook. Every “slay queen” and “no cap” comes with a pause, like they’re mentally checking if they deployed it correctly.

What makes this painful is the time delay. By the time a boomer discovers a term, learns what it means, gets comfortable using it, and finds an opportunity to deploy it, that slang is already linguistically deceased. They’re essentially performing CPR on dead language while younger people watch in horror. “Adulting is hard!” they announce, not realizing that millennials retired that term when it became a wine-mom wall decal.

2. The aggressive Instagram presence

Their Instagram looks like an AI trained exclusively on “how to Instagram” articles from 2016. Every sunset has #blessed. Every meal has #foodie. Every photo has seventeen hashtags, including #instagood, #photooftheday, and somehow, inexplicably, #followforfollow. They post motivational quotes in fonts that went out of style when Myspace died, complete with their own commentary that explains the obvious message.

The real tell is the comment interaction. They respond to every single comment with the enthusiasm of a golden retriever, using too many emojis and signing their name like it’s an email. “Thanks sweetie! Hope you’re well! – Aunt Linda.” They treat social media like a formal correspondence when it’s supposed to be casual, turning every interaction into an awkward digital receiving line.

3. Mentioning their one young friend constantly

“My friend Tyler—he’s 28—says that all the time!” This mythical younger friend becomes their credibility card, mentioned within the first five minutes of any conversation about contemporary culture. Tyler (who’s probably just their coworker who’s polite) has apparently explained everything from TikTok to cryptocurrency to them, making them an expert by proximity.

The constant Tyler-dropping reveals the insecurity underneath. They need you to know they’re not isolated in their age bracket, that young people voluntarily spend time with them. But it has the opposite effect—it highlights how unusual they find intergenerational friendship, like they’re anthropologists who’ve made contact with a rare tribe. Tyler, meanwhile, is just trying to get through his workday.

4. The trying-too-hard casual dress

They show up in Supreme hoodies, Yeezys, and distressed jeans that cost more than a mortgage payment in 1975. But something’s always slightly off—the jeans are distressed in the wrong places, the hoodie is worn too formally, the sneakers are too clean. They look like someone dressed them for a “hello fellow kids” Halloween costume.

What gives it away is the discomfort. They’re constantly adjusting, checking if things look right, asking if this is “too much.” They treat streetwear like a uniform they’re not sure they’re wearing correctly. The effort to look effortless is exhausting to watch. Their previous comfortable style was actually more youthful than this cosplay of youth.

5. Oversharing their progressive credentials

Within minutes, they’ve mentioned their gay friend, their thoughts on gender pronouns, and how they’ve “always been ahead of their generation” on social issues. They list their progressive stances like they’re checking boxes on a generational visa application. “I supported gay marriage before it was cool,” they announce, expecting a medal for basic human decency.

This performance of progressiveness feels hollow because it’s still centered on them getting credit. They want points for attitudes that younger generations consider baseline humanity. The trying-too-hard allyship actually reveals the generational divide more starkly—they think these are special positions rather than minimum requirements for being a decent person.

6. The TikTok account nobody asked for

They joined TikTok to “understand what the kids are up to” and now post videos of themselves attempting dances with the rhythm of a metronome having a panic attack. Their content alternates between explaining things everyone already knows and attempting trends that died six months ago. The comments are turned off after their first video got ratio’d into oblivion.

The painful part is the view count. Seven views, three of which are them checking if it uploaded correctly. They don’t understand the algorithm, the culture, or the unspoken rules. They’re posting digital content like it’s a TV broadcast, not realizing that TikTok is a conversation they’re having with themselves.

7. Explaining technology incorrectly

“I’m pretty good with technology,” they announce, before explaining how “the Facebook” works to someone who coded their first website at age twelve. They’ve learned just enough tech vocabulary to be dangerous, throwing around terms like “algorithm” and “cloud” with the accuracy of a storm trooper. They’re confident because they can restart a router, not realizing that’s the equivalent of knowing how to use a can opener.

They offer to help younger people with computer problems, not understanding that the skills gap has reversed. Their knowledge peaked with Windows XP, but they’re still operating on the assumption that age equals tech wisdom. Watching them explain how the internet works is like watching someone explain aviation while thinking planes flap their wings.

8. The forced casualness about everything

“Whatever’s clever!” “It’s all good!” “No worries!” They’ve adopted a laid-back attitude that feels like a full-body cramp. Every interaction is aggressively casual, like they’re constantly proving they’re not uptight. They’re so chill they’re practically frozen, responding to everything with manufactured ease that screams internal panic.

This forced casualness extends to everything—they’re cool with whatever restaurant, whatever music, whatever plans. But their “whatever” energy vibrates with the frequency of someone who definitely has preferences but thinks having opinions makes them seem old. The performance of not caring takes so much effort that it’s the most caring thing in the room.

Final thoughts

The real tragedy here isn’t that boomers are trying to connect with younger generations. That impulse is actually sweet. The tragedy is that in trying so hard to be something they’re not, they’re hiding what they actually have to offer. Their genuine experiences, their different perspective, their actual personalities—all buried under a pile of dead slang and uncomfortable sneakers.

Younger generations don’t need boomers to be cool. They need them to be real. The forced relatability creates more distance than any age gap ever could. When someone’s performing youth, they can’t actually connect with youth. They’re too busy monitoring their own performance to have a genuine interaction.

The irony is that the boomers who don’t try—who wear their New Balance unselfconsciously, who admit they don’t understand TikTok, who share their actual interests instead of pretending to like trap music—are the ones younger people actually enjoy. Authenticity is ageless; trying to be ageless is aging.

Here’s the truth: every generation becomes uncool. Millennials are already there, desperately clinging to skinny jeans while Gen Z laughs. The cycle continues, and fighting it just makes it worse. The coolest thing any generation can do is accept their place in the timeline with grace, humor, and the wisdom to know that trying to sit at the kids’ table when you’re sixty just makes everyone uncomfortable—especially the kids.