When Your Best Friend Becomes Your Underminer: A Cautionary Tale

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Throughout my twenties and early thirties, I found myself in whirlwind friendships with women who were just as unsuitable for me as some of the partners I dated. The pattern was always the same: I’d meet someone new who seemed fantastic. We’d bond over shared interests, quickly morphing into inseparable pals, mistaking this closeness for true friendship, and labeling it “best friendship” before we’d really had a chance to build a solid foundation.

I often opened up too quickly, spilling my secrets and showering them with supportive words that felt disproportionate to our short history. I enjoyed being the go-to person during their crises—crises that seemed alarmingly frequent given how little time we’d spent together. But inevitably, I would drop the ball during one of their many dramas, and they’d accuse me of not living up to the standards I had helped create.

Suddenly, the title of “best friend” felt like a heavy wool sweater I couldn’t take off without someone else unbuttoning it. We were both guilty; we had rushed into declaring ourselves best friends without taking the time to genuinely connect.

This happened about four times, which feels like at least three too many. Once I recognized the type of woman I was drawn to, I tried to tune in to the warning signs and pay attention to that unsettling feeling in my gut when something felt amiss. I slowed my roll, hoping to build friendships more thoughtfully. So, when I met Clara*, I thought I had finally cracked the code.

Clara was eager to accelerate our friendship, but I kept a slower pace. She was charming and funny, and being around her was a blast. Yet, each time I left her company, I felt drained or bad about myself. Unable to pinpoint why, I ignored the red flags and let the friendship gain momentum, chasing that elusive sisterly bond I craved.

One night over dinner, we had a conversation that stung me deeply, so much so that I documented it when I got home. “I’m going on a blind date,” I shared. Clara, wiping her mouth after devouring some spicy chicken, perked up, “With who?”

“Someone Maggie set me up with,” I replied. “Do I know him?” she asked, leaning closer. “No, he lives upstate,” I said. “Where upstate?” “Tivoli, I think. Maybe Cold Spring.”

Her expression changed dramatically. “Really? You’re being set up with him?” “Yeah, why?” I was suddenly uneasy.

“Do you know what he looks like?” she probed. “No, is it awful?” I felt a knot in my stomach. “No. It’s not awful. He’s stunning—like, super-good looking and funny. I just don’t see the connection.”

I was taken aback. “So, I’m ugly and boring?” I crumbled my napkin in frustration. “No! I just don’t get it. He’s so attractive! Why would he be interested in you?”

For weeks after that, I couldn’t shake the feeling of being unattractive and dull, even as I was included in a New York Times feature about cultural influencers. Clara was the last person to call me that day. “I guess you had a good day,” she remarked, her tone prickly.

“Yeah. I got a writing gig,” I replied. “Oh, like a blog post or something?” “No, it’s actually for a feature at New York Magazine.”

“Wait, what? They want you to write for them? Like, the cover story?” “I guess,” I said.

Her tone turned accusatory. “How did they even know who you are? You just had your photo in the paper. It was just a photo!”

“Do you think it matters?” I shot back, my patience wearing thin. “I sit at home pitching magazines, and you get this great assignment because of a photo? How is that fair?”

“Maybe you’re just happy being known.” Clara’s words were a jab I wasn’t prepared for. It made me question my worth.

The day after our conversation, I tuned into a segment on This American Life where Mike Albo discussed his book, The Underminer: The Best Friend Who Casually Destroys Your Life. Listening to him impersonate that insincere friend struck a familiar chord. Clara wasn’t just a friend; she was an underminer.

This epiphany hit me harder than any label I’d used before. While I had previously described these friendships as narcissistic, “underminer” resonated more deeply. It captured the essence of how I felt—like my self-worth was being chipped away. Understanding this freed me to step away from Clara with confidence.

Recognizing this new terminology allowed me to reflect on my past friendships. I realized that the friendships that truly mattered had formed over time, grounded in genuine love rather than a swift, platonic infatuation.

Yet, in acknowledging Clara as an underminer, I also had to admit I had played a role in this dynamic. I had rushed into friendships, undermining the chance for true connection.

Clara was the last underminer to infiltrate my life. Now, equipped with the ability to identify the signs and trust my instincts, I’ve been able to steer clear of insincere friendships. Although I had previously ignored the warning signs, I now prioritize my intuition, ensuring that I surround myself with supportive and genuine people. And since that realization, I’ve been happily underminer-free! (*Names changed to protect the not-so-innocent.)

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To learn more about managing friendships and personal growth, consider checking out our other blog post.

Summary

Navigating friendships can be tricky, especially when you discover that a so-called best friend may actually be undermining your self-esteem. Reflecting on my past relationships, I recognized a pattern of rushing into friendships without allowing genuine connections to form. By learning to identify the signs of an underminer, I’ve empowered myself to cultivate healthier friendships that enrich my life.

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