8 things boomers do when trying to befriend younger people that make it awkward instead of natural

Have you ever watched someone try so hard to connect that they end up creating the exact opposite effect?

I saw this happen last week at my local farmers' market: A vendor, probably in his late sixties, was desperately trying to relate to his young customer by peppering his conversation with words like "lit" and "no cap."

The twenty-something buyer smiled politely, but I could see the discomfort written all over her face.

Genuine connection across generations requires authenticity and awareness of certain habits that can make interactions feel forced rather than natural.

As someone who regularly mentors young women entering finance, I've learned firsthand what works and what doesn't when building relationships across age gaps.

And trust me, I've made my share of mistakes along the way.

If you're a boomer looking to build authentic friendships with younger people, whether they're colleagues, neighbors, or even your own kids' friends, these eight common missteps might be standing in your way:

1) Overusing outdated slang to seem "hip"

Nothing screams "trying too hard" quite like dropping "groovy" or attempting to use Gen Z slang you learned from a BuzzFeed article.

When I first started mentoring, I thought using younger language would help me connect. I'd say things like "that's fire" in meetings, thinking it made me relatable.

One brave mentee finally told me it felt like watching her dad try to dance to TikTok songs.

Ouch, but point taken!

Young people need you to speak authentically: Your own vocabulary, your own expressions, and your own way of communicating is perfectly fine.

In fact, it's refreshing.

The minute you start forcing slang that doesn't come naturally, you create a barrier instead of breaking one down.

2) Constantly comparing everything to "the good old days"

"Back in my day, we didn't have smartphones and we turned out just fine!"

Sound familiar? While nostalgia has its place, constantly framing conversations through the lens of how things used to be can make younger people feel like their reality is being dismissed or judged.

I catch myself doing this sometimes, especially when discussing workplace culture.

But here's what I've learned: Every generation faces unique challenges and opportunities.

Instead of comparing, try being curious.

Ask questions about their experiences without immediately relating them to your own past.

3) Dismissing their concerns as "just a phase"

Career anxiety, climate change worries, social media pressure; these are real concerns for younger generations.

When my father had his heart attack at 68, it made me deeply grateful I'd left corporate stress behind.

However, it also taught me something important: stress and worry look different for every generation.

What younger people experience today in terms of economic uncertainty or social pressure is vastly different from what we faced, and dismissing these concerns creates emotional distance.

Listen without minimizing, and validate without comparing.

Sometimes, the most powerful thing you can say is simply, "That sounds really challenging."

4) Oversharing on social media or texting too formally

Have you ever received a text from someone that reads like a formal letter?

"Dear Sarah, I hope this message finds you well. I am writing to inquire about your availability for coffee next Tuesday at 2:00 PM. Please advise at your earliest convenience. Sincerely, Bob."

Maybe you've seen the opposite: The boomer who comments on every single post with lengthy paragraphs or uses Facebook like it's their personal diary?

Finding balance in digital communication is tricky, but here's a simple rule: Match the energy and format of the platform.

A text can be casual, while an Instagram comment doesn't need to be an essay.

Please, one exclamation point is usually enough.

5) Giving unsolicited life advice

"You know what you should do..."

These six words can shut down a conversation faster than almost anything else.

Young people today have access to more information than any generation before them.

They're not lacking in advice; they're often overwhelmed by it.

When I started mentoring, I thought my job was to dispense wisdom but I quickly learned that listening was far more valuable than lecturing.

Now, I wait to be asked for advice, and even then, I often respond with questions rather than answers.

"What do you think would happen if...?" tends to open doors that "You should..." immediately closes.

6) Making assumptions about their work ethic or values

"Millennials are so entitled."

"Gen Z doesn't want to work."

These sweeping generalizations are conversation killers.

Every generation has been criticized by the ones before it, and these stereotypes prevent real connection.

I've mentored young women who work harder than I ever did at their age, juggling multiple gigs, student loans, and a job market that's completely different from the one I entered.

Their values might be expressed differently, prioritizing mental health or work-life balance, but that doesn't make them less valid or less hardworking.

7) Trying to parent or mentor when friendship was the goal

This is perhaps the trickiest balance to strike.

When you're older and have more life experience, it's natural to want to guide and protect.

However, if you're trying to build a friendship, constantly slipping into a parental or mentor role changes the dynamic entirely.

I learned this the hard way when attempting to befriend younger neighbors.

Every conversation became a teaching moment on my part.

It wasn't until I started sharing my own struggles and uncertainties that real friendship began to develop.

Vulnerability—not wisdom—was the bridge.

8) Avoiding difficult or contemporary topics

Mental health, gender identity, systemic racism; these are human topics.

When I finally had honest conversations with my parents about mental health, breaking generations of silence on the subject, it transformed our relationship.

Similarly, being willing to engage with topics that might feel uncomfortable or unfamiliar shows younger people that you're interested in their whole world.

You don't have to be an expert because all you have to do is just have to be willing to learn and listen.

Asking genuine questions, like "Can you help me understand...", goes much further than avoiding these conversations altogether.

Final thoughts

Building genuine friendships across generations is about bridging it with authenticity, respect, and genuine curiosity.

The young vendor at my farmers' market doesn't need me to know the latest memes or speak in TikTok references.

What creates connection is when I ask about her growing methods, share my own gardening disasters, and treat her as an equal despite our age difference.

Making friends as an adult requires intentional effort and vulnerability at any age but, when you're trying to connect across generations, it also requires letting go of the need to be seen as relevant or cool.

You're already relevant; your experiences, your perspectives, and your authentic self.

Stop trying so hard to be understood and start trying to understand.

The friendships that develop from that shift might surprise you with their depth and mutual benefit.

After all, connection is about showing up as yourself and making space for others to do the same.