That&#x27;s the clincher for me. If she&#x27;d enjoyed that - and it&#x27;s at least conceivable that someone would take it as a compliment - then the boss wouldn&#x27;t know and no harm would be done.<p>Remember, it&#x27;s perfectly legal to date your coworkers. You can ask them out and everything! But the moment they move to stop your advances, you <i>must</i> cease immediately. It sounds like she was at least initially open to out-of-work conversation (as evidenced by her agreeing to switch to WhatsApp), but once she become uncomfortable it should have ended.<p>Acceptable:<p>You: We should go out sometime. I&#x27;ve never asked before, but would you be interested?<p>Your colleague (NOT subordinate): No.<p>You: OK, back to business. Hey, what time did they move our meeting to?<p>Not acceptable:<p>You: I know I ask you this daily, but...<p>You: I&#x27;m not really supposed to date people who report to me, but...<p>You: We went out one time and you broke it off, but...<p>You: This was OK last week before you asked me to stop, but...