First, a little background. My niece, a millennial, lives in New York City, about an hour from my Long Island home. Over the years, I’ve tried to embody the role of “Cool Aunt,” hitting some of the tropes associated with this ever-evolving term and with varying degrees of success. I’ve had exciting careers, traveled extensively, pivoted my life paths, thrown memorable parties, and, yes, overshared on occasion. Does this overqualify me or underqualify me for the job? Unclear…

A Boomer’s Guide

Two summers ago, I threw out what I thought was an innocuous invite: I’d host a party for my niece and her friends. Truthfully, it might have been an impulse invite, the kind of thing you toss out in the spirit of the moment. But as I began planning, a hint of imposter syndrome crept in. Do they really want to spend time with me? Was I coming off as the cringy aunt instead of the cool aunt?

I’d shared cocktails with my niece and her friends a week prior, and I was impressed by their resilience and refreshingly positive outlook. They seemed to glide through the chaotic maze of single professional life in New York City with a grace that was notable. As someone who’s spent the last fifteen years cheering for young women—whether through admissions advice, career coaching, or just being the world’s greatest giver of unsolicited wisdom, I was feeling confident and optimistic.

Overcoming Doubts: Generations United

Life, as it often does, threw a wrench in my plans. The event, affectionately dubbed the YPP (Young People’s Party), their name, not mine, kept getting postponed. But the girls kept after me, reminding me to get a date on the calendar. Relieved that they seemed to really want this to happen, I felt assured that my fears were unfounded. The stars aligned, my schedule cleared, and I decided it was finally time. With a renewed sense of purpose and help from my 30-something daughter, we set out to bring this party to life.

Coastal Chic Meets Imposter Syndrome

When it comes to hosting, I don’t half-ass things. First, we chose a theme. I picked a Coastal Chic vibe (think hydrangeas, wicker, and floral prints).
Invitations were sent, and I curated a summer menu that included fresh corn and farmstand peaches. As I put the finishing touches on the monogrammed tote bags filled with swag, I found myself wondering again: Am I trying too hard? Would they see me as “too extra”? I felt a little trepidation, but there was no turning back at this point.

Did I Accidentally Step into a Nancy Meyers Movie?

Party time. The house was ready, and the backyard got a glow-up. Food was prepped. The welcome mat was out. The guest list was a mix of my niece’s and daughter’s friends—a group of bright, ambitious professional women making their marks in finance, consulting, HR, and even as influencers. My daughter, the only married among them, brought her just-married-this-year glow. It promised to be a fun celebration of vibrant, young energy.

As the party unfolded, I found myself leaning in. Sure, I asked way too many questions and played the “hostess with the mostest” role perhaps a bit too eagerly, but I stopped worrying about trying to be “fun”. We cooked, ate, swam, and relaxed. I thought about the world of millennials compared to mine at the same age. The topics they discussed—career ambitions, travel plans, and finding a partner—were universal themes I’d wrestled with three decades earlier. Yet, their lives seemed even more exhausting and frenzied, thanks to the added pressures of dating apps and social media. As I marveled at their fearless attitudes, I realized—I didn’t feel out of place at all. I wasn’t invisible, nor was I some awkward outsider.

How Intergenerational Connections Can Boost Relevance

Then came the surprise activity: a portrait painting session. I set up canvases and paints and challenged everyone to paint the person sitting across from them. I loved nudging these confident ladies out of their comfort zones. The result was a hilarious mash-up of talent and creative expression. Each painting somehow captured the essence of its subject, if not the actual likeness. It was pure, unfiltered fun.

Everything clicked as I looked around the table at these remarkable millennials. There’s something vital and energizing about these kinds of connections. They remind us that our relevance doesn’t disappear with time, it adapts and can even flourish through these social interactions.

My Takeaways: Beating Imposter Syndrome and Staying Relevant at Any Age

I emerged from this 12-hour extravaganza not drained but positively energized. I felt like the leading lady in my own Nancy Meyers movie. Spending time with these young women was affirming. I was inspired, happily exhausted, and maybe even a little wiser. Hanging out with young women 30 years younger isn’t just entertaining; it’s downright nourishing.

Imposter syndrome might hit at moments when you least expect it, but I’ve learned that embracing intergenerational relationships, even when you’re unsure, can help maintain your own vibrance and vitality. So, the next time you’re invited to a “Young People’s Party”, don’t hesitate. Go. Dive in. Or better yet, host one yourself. You’ll feel cooler—and maybe even younger—just by taking part.

****Cover Art Credit: Noelle Crooks – author of recent release Under the Influence

Do you spend regular time with young people?

What are some of your favorite activities to enjoy with them?