9 ways boomers try to relate to millennials that come across as trying too hard

Ever notice how some conversations with older colleagues or family members feel a bit... forced?

Last week at the farmers' market, I watched a volunteer in her sixties approach a group of younger vendors with "Hey fam, your booth is totally lit!" The awkward silence that followed was palpable. She meant well, genuinely trying to connect, but something about it just didn't land.

This got me thinking about all the times I've witnessed well-meaning boomers trying to bridge the generational gap with millennials, only to have their efforts backfire spectacularly. Look, I get it. Connection across generations is important, especially in workplaces and families where we need to understand each other. But sometimes the trying itself becomes the barrier.

Having spent years in finance before transitioning to writing, I've seen this play out in corporate settings, family gatherings, and everywhere in between. The intention is usually pure, but when the effort feels performative rather than genuine, it creates distance instead of closeness.

So let's talk about the most common ways this happens and why they miss the mark.

1) Using outdated slang (or worse, current slang incorrectly)

Nothing makes a millennial wince faster than hearing "adulting is so hard, am I right?" from their 65-year-old boss. Or the classic "I'm shook" used to describe mild surprise at a quarterly report.

The thing is, language evolves quickly, and by the time certain phrases make it to mainstream boomer vocabulary, they're often already dated or being used incorrectly. I once sat through a presentation where a senior executive kept saying things were "bussin'" when she meant "busy." The secondhand embarrassment was real.

What works better? Just speak naturally. Authenticity beats forced coolness every single time. Millennials appreciate genuine conversation far more than awkward attempts at speaking their language.

2) Oversharing about their one millennial friend or child

"My daughter is a millennial too, and she loves avocado toast!"

Sound familiar? This tendency to reference the one millennial they know well as if they're a representative for an entire generation comes up constantly. I've lost count of how many times someone has told me about their niece who "also works in tech" as if that creates an instant bond between us.

The problem here is that it reduces individuals to generational stereotypes. Just because someone knows one millennial doesn't mean they understand all millennials. We're not a monolith, and these comparisons often feel reductive rather than relatable.

3) Making everything about participation trophies

Can we retire this joke already?

Whenever workplace discussions turn to recognition or feedback, there's often that one boomer who chimes in with "Well, millennials need their participation trophies." The irony? Millennials didn't give themselves those trophies. That was a boomer parenting trend.

This constant callback to a tired stereotype shuts down real conversation about workplace motivation and recognition. It's dismissive and, frankly, lazy. Real connection happens when we move past these worn-out generalizations and actually listen to what individuals value.

4) Pretending to love technology they clearly don't understand

"I'm on the TikTok now! Do you follow the TikTok?"

The overenthusiasm about platforms they don't actually use or understand is painful to watch. I've seen executives claim they "love Instagram" while holding their phone upside down trying to take a photo. Or the classic move of commenting "LOL" on someone's sad news because they think it means "Lots of Love."

Here's a radical idea: it's okay to not be on every platform. It's okay to admit you prefer phone calls to texts. Millennials actually respect the honesty. What feels forced is the pretense of being digitally native when you're clearly not.

5) Dismissing genuine concerns with "back in my day" stories

Student loans, housing costs, climate anxiety. These are real issues affecting millennials, but too often, attempts at connection turn into comparison contests.

"Back in my day, we just worked hard and bought a house by 25!"

These stories, meant to inspire or relate, often come across as tone-deaf. The economic landscape has fundamentally changed. When I left finance, I had colleagues who couldn't understand why younger employees stressed about money when "the job pays well." They failed to account for the massive student debt and housing costs that didn't exist in their era.

Acknowledging different challenges rather than dismissing them creates actual connection.

6) Forced casual Friday enthusiasm

"Look, I'm wearing jeans! Just like you guys!"

The performative casualness, especially in workplace settings, often feels more awkward than just maintaining professional dress. There's something uncomfortable about watching a usually formal manager trying too hard to be "chill" because they read millennials prefer casual work environments.

Authenticity matters more than dress code. If you're comfortable in a suit, wear the suit. We can connect across differences without everyone pretending to be the same.

7) Explaining things millennials already know

"Have you heard of this thing called a podcast? It's like radio but on the internet!"

The condescending explanations of technology, trends, or concepts that millennials invented or popularized is exhausting. I once sat through a meeting where someone explained what "going viral" meant to a room full of digital marketers in their thirties.

This oversimplification suggests millennials need basic concepts explained to them, which is both insulting and counterproductive. Most millennials have been using technology professionally for over a decade. We got this.

8) Weaponizing therapy language incorrectly

"I need to create boundaries with this deadline. It's giving me trauma."

The sudden adoption of therapy speak, often used incorrectly, feels performative rather than genuine. Having had honest conversations with my parents about mental health after years of generational silence, I deeply value when older generations engage with these concepts. But there's a difference between genuine growth and throwing around buzzwords.

Millennials appreciate when boomers engage with mental health concepts authentically. What feels forced is using this language without understanding its meaning or trivializing genuine mental health terminology.

9) The aggressive social media friend requests

Nothing says "trying too hard" like the boss who friend requests all their millennial employees on every platform, then comments excessively on personal posts.

"Great pic, Sarah! See you Monday! 😎🔥💯"

Professional boundaries exist for a reason. The attempt to be the "cool boss" who's friends with everyone on social media often backfires. It makes professional relationships awkward and personal space feel invaded.

LinkedIn? Sure. Instagram, TikTok, and Snapchat? That's crossing into trying-too-hard territory.

Final thoughts

Here's what actually works: genuine curiosity, respectful questions, and acknowledging differences without trying to erase them.

The best intergenerational connections I've witnessed happen when people show up as themselves. When my mother introduces me as "my daughter the writer" now instead of clinging to my finance past, it shows she sees who I am today. That's real connection.

Millennials aren't looking for boomers to be just like them. We're looking for mutual respect, understanding, and authentic interaction. Skip the forced slang and participation trophy jokes. Instead, try asking genuine questions, listening to the answers, and finding common ground that doesn't require anyone to pretend to be something they're not.

The generational gap doesn't need to be bridged by everyone standing on the same side. Sometimes the beauty is in building a strong connection that spans the divide while allowing everyone to stand firmly where they are.