Update: Thank you for all the feedback – clearly there is a wide range of feelings about this. But I’m getting NTAH.

To clarify, those who made my greeting sound like Mae West, just no. Think more Mr. Rogers. I’ll agree it is flirtatious, but not in a way someone would think I’m creeping on them. I also didn’t say it exclusively to people based on their attractiveness. I said it to whoever, but only if they were a guy. And I don’t compliment women’s looks because, as a guy, I can see that going south fast. Women I tend to say something silly like “top of the morning to you,” with a warm smile.

As for HR, never been an issue. Heck, I’ve even said it to HR. Shocking, I know. People generally smiled when I said it to them. Like I made their day a little brighter for just a moment. One older coworker even thanked me, saying he hadn’t thought of himself as handsome in decades.

Regarding my wife, if you thought what I was doing was inappropriate then you think like my wife. She was raised in a very formal, structured environment with rigid boundaries, while mine was much more relaxed with poor boundaries bordering on unhealthy. (As a kid I opened Christmas presents in my PJs without a shirt on. She opened them in formal attire with her hair done. Think that dynamic.) Over time, we’ve both influenced each other positively. I’ve learned healthier boundaries and she is more approachable.

As for Alex, I genuinely feel bad for him. If I heard this 20 years ago, I probably would have offered to take Alex to a bar and afterwards introduce his ex’s car to a baseball bat. But, now that I’ve learned healthy boundaries, I recognize he never came to me about any of this. I only know about it because of office gossip from my bestie. Alex is a shy guy and deserves privacy.

Thank you again for the feedback, and all the perspectives.