Hearing stories similar to these from the view of my wife, and women I have worked with professionally, who have silently put up with this kind of stuff on a regular basis throughout their careers. Well, that has made me rethink what is/isn't appropriate in a public/professional setting and stuff like this now makes me cringe because I know how others around me may silently feel about it.

I have no idea what the relationship between the OP and his female colleague was at the time. Sounds like they were on same page. But in 2019, in a professional setting, why risk it. His colleague could have justifiably gone to HR and made a stink over how uncomfortable it made her feel.