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I’m Gen Z, my aunt is a boomer; when I needed help with my crush, she was the perfect confidant

September 4, 2025
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I’m Gen Z, my aunt is a boomer; when I needed help with my crush, she was the perfect confidant
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The author poses with her aunt at an outdoor light instillation.
My friends don’t always give me great dating advice, but my aunt offers a fresh perspective when I need it.

Courtesy of Nicole Benedettini

“I was getting worried, I saw all these messages,” my aunt said in a WhatsApp voice message, her voice panicked and relieved at the same time. She was at a dinner with friends and thought something terrible had happened to me.

On a Wednesday evening in June, I had sent her seven voice messages between 9 and 11 p.m., four of which were about my new crush. I was very excited and wanted to tell her that we had begun following each other on Instagram, as well as share other details about our meeting.

I’m a 26-year-old Gen Z woman who is most comfortable communicating via WhatsApp and Instagram. At 61, my aunt just squeaks in as a young baby boomer. She came of age in an era when mobile phones, social media, and dating apps didn’t exist. Nevertheless, she is one of my favorite people to turn to when I want dating advice.

Her nuanced approach can be very beneficial

Previously, I often relied on my friends for love advice. One gave suggestions like waiting for men to make the first move, which I found too cautious. While another friend is a bit more bold with her advice and cheers me when I am thinking of asking someone I like out. In reality, I sometimes need an approach that stands between these two. That’s where my aunt comes in.

When my aunt sees I am being indecisive, she often tells me, “Do what you feel like doing.” At first, this advice was annoying to hear, as I wanted more explicit guidance. Now I understand that she doesn’t want to push me if she thinks I am not ready, giving me time and space to reflect and expand on my motivations before taking the initiative.

Still, she knows I am shy and self-conscious, so her feedback can be more gutsy if she thinks making a move is the best course of action.

She gave me the push I needed to make a move

Earlier this summer, I had a crush on my group fitness instructor. One day, several weeks after the WhatsApp voice messages I sent my aunt about him, a girl I had never seen before accompanied him to the workout. My gut instinct strongly suggested she was his girlfriend.

Since my aunt and I live next to each other, when I got home, we discussed my dilemma in our shared garden. After listening carefully, she encouraged me to send him a message on Instagram and flat out ask if she was his girlfriend. Initially, I said I couldn’t do it because I was too embarrassed. But soon realizing I didn’t want the agony of not knowing to eat away at me, I changed my mind.

Based on my aunt’s urging, I wrote him a straightforward message, telling him I hoped I wasn’t being inappropriate in asking if that girl was his girlfriend. I added that I was intrigued by him and was interested in asking him out at some point.

I waited a few minutes for his response, feeling anxious and hopeless. Then, I got a notification.

He kindly thanked me for the compliment and honesty, and confirmed that they were dating. While his answer made me sad for a few days, it provided the closure I needed to stop fantasizing over him.

I credit my aunt for persuading me to untangle this situation, because I hadn’t even thought of asking him about the mystery girl on my own. More importantly, I am grateful to have someone to turn to when I need a fresh perspective and a little extra encouragement.

The post I’m Gen Z, my aunt is a boomer; when I needed help with my crush, she was the perfect confidant appeared first on Business Insider.

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