Get your tea, I had an interesting evening. 🍵 The wildest fantasies of our younger selves can be so misguided, and it's bittersweet when they come true.

A few years ago I had a massive crush on what is now my former boss. The guy was super competent, handsome, respectful, kind, and mentored me, and ensured my advancement at the company. I thought he was a total HVM.

He is a smart guy and I think he picked up on my crush. I never made any moves cause coworker and thought even back then, if he wants to, he would.

He and I both switched companies about a year ago and ended up in the same city. We had each other's numbers but didn't keep in touch. He texted me out of the blue last week to ask to catch up over a dinner. 👀 My intuition pinged this was weird. Why now after a year? 🚩

I debated declining, maybe I was imagining subtext and he wanted to have a kosher professional networking dinner, so I accepted his invitation.

Day of, he texts me to ask what our plans are. 🚩 I gave plenty of advance notice in my availability so this was unimpressive, even if it was only a professional meeting.

He tells me he's happy with any price range and that he shares my love of fine dining. I tell him what cuisines I like and suggest he picks one. He struggles with finding an open reservation - duh, it is well known in our city that you don't just secure one Friday night 🚩 - but finally gets one for a cuisine I don't enjoy (he wasn't aware so not the worst). I didn't wanna be a cool girl™ or continue to play phone tag, so I tell him a place I like and we get a res.

He picks me up (I trust him on a reasonable colleague level), and we enjoy the dining and catching up about work and life. I'm feeling tentative flirting vibes from him but keep a cool friendly professional exterior since he had really not impressed me so far.

The conversation was also unimpressive, and I got the vibe he was nervous around me. I have really leveled up my looks and style and feel more confident, so I wasn't the mousey employee he was used to.

The real mea culpa is when the cheque arrives. It was a pricey restaurant, and the guy can easily afford it. He did not offer to cover my share. 🚩 He did in the past for his employees as many managers do, and has several years of experience on me and earns more, and invited me out, so even if this was only professional, imo he should have paid.

I got so turned off, I'm embarrassed I accepted the invite. This guy was legit one of the biggest crushes I've ever had (yes I was a pickme). The progress in my discernment is clearly on point. 👑

Ladies do you have any disillusionment stories?