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Navigating Workplace Crushes Without Crossing Lines

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Chapter 1: The Dilemma of Attraction

As a man in my fifties, I find myself collaborating with the stunning Donna, who is truly a knockout. I take pride in the fact that I haven’t made any suggestive comments or weird remarks like, “If I were only a couple of decades younger…” Instead, I focus on her professional abilities, which are as impressive as her appearance.

It’s frustrating that my respectful demeanor often goes unnoticed. I wish attractive women would recognize that I’m genuinely respectful. Let’s say it together: “Not creepy.”

Despite my self-control, I have contemplated what it would have been like to be younger. Back then, I might have been more forward. If she confided in me about feeling overwhelmed and needing a break, I might have jokingly responded, “Breather? I barely know her!”

When I shared these thoughts with my therapist, she pointed out that such an attitude could be a form of self-sabotage. She suggested that I should express my feelings towards Donna. I was adamant: “Absolutely not! She’s way out of my league.” Not that I believe in leagues—well, maybe I do.

My therapist encouraged me to consider the notion of being “out of my league,” suggesting it’s a limiting belief. I told her I found it hard to take her advice seriously because she was covered by my public insurance plan.

Lunch outings with Donna are my favorite moments since they allow me to admire her beauty without interruption. For Valentine’s Day, I gave her a card saying, “I’m okay with the ‘friend zone’ if that’s all you want,” along with three dozen roses and a month’s membership to a fancy spa.

However, I felt underappreciated and decided to create a personalized mug that read, “Not Creepy. World’s Nicest Guy.” I wrapped it up and presented it to her in front of our colleagues in the open office.

Her reaction was lukewarm, which surprised me. I mentioned that I had crafted the phrase myself, prompting only an awkward half-smile from her. To lighten the mood, I joked, “You don’t like it? Wow—because I’m actually a cunning linguist.” Two temp interns nearby found it amusing.

The following day, she asked if we could have a private discussion. I met her in the break room, where she was joined by the HR manager. She complimented me for being nice and acknowledged that she appreciated my lack of creepiness. That was kind of her. However, she made it clear that we were simply work acquaintances and should keep our interactions strictly professional.

I got the message. In an effort to maintain good communication, I suggested she join a couple of my therapy sessions. I assured her my therapist would back me up, and it wouldn’t cost her anything under our insurance. She exchanged looks with the HR manager before they both left.

That wasn’t a flat-out rejection. I felt validated by her compliment and eagerly anticipate our next lunch together. I can't help but wonder if she would ever consider being more than just a colleague.

Chapter 2: The Unwanted Attention

This video explores the unsettling side of social media, focusing on creepy TikToks that can disturb your peace of mind, especially at night.

Another look at eerie TikToks that are best avoided after dark, illustrating how online content can sometimes cross the line into the uncomfortable.

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