Dilemma: I thought we had a connection but now I'm not sure

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May 14, 2025 • 20 mins

This week’s dilemma:

“I genuinely thought we had a connection, but now I feel like I’ve made a fool of myself.”

In this minisode, we respond to a listener who built a real connection with a colleague, until things suddenly got weird. The inside jokes and meme swaps have turned into short replies and cold shoulders, and now she’s left wondering: Did I overshare? Did I get too close? Or was it never what I thought it was?

If you’ve ever blurred the lines between work and friendship and then had to navigate the fallout, this one’s for you.

Got a work dilemma?

We’re answering real-life listener dilemmas all season long. Send yours to dilemma@thisisworkwell.com and we'll keep it anonymous, always.

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