Sexual Harrassment Policy be DAMNED! I'm in LOVE with my Assistant!

Edward Stratton III and Kate Summers from Silver Spoons
Daddy Warbucks and Grace Farrell from Annie
Fiorello LaGuardia and Marie from Fiorello!

There’s got to lots more. Have you got any to contribute???

Secretary was a really messy sexual harassment suit that never happened.

How to Succeed in Business Without Really Trying, if I remember.

Well, if you’ll stretch the definition of “assistant” to include anyone that works for you…

Maxwell Sheffield and Fran Fine from The Nanny.

My Fair Lady?

No, ya pervs, at the end, when he tells Eliza to get his slippers or something…

Donna and Josh from The West Wing, although they didn’t consummate until she cough got out from under him.

And, of course, 9 to 5 is an example of the Sexual Harassment Policy being damned, so the women resort to their own retribution against the boss. Not sure it’s quite in the same spirit for this thread.

The song “Take a Letter, Maria.”

Dave Nelson and Lisa Miller in NewsRadio

Not exactly in LOVE, but George Bluth Sr. and Kitty from Arrested Development

Frederick Frankenstein and Inga in Young Frankenstein.

I don’t know about Igor…

Sam and Diane on Cheers

Captain von Trapp and Maria in The Sound of Music

Leo Bloom and Ulla from the musical version of The Producers.

Dr. Egon Spenkler and the receptionist, Janine Melnitz, from “Ghostbusters.”

“Why good heavens Miss Jones! You’re beautiful!”

I think all three of your examples predate sexual harassment law being a big deal.

That said:
Fran the Nanny and whatever her boss’s name was.
Picard and the Lt. Cmdr. in astrophysics he was involved with.
Bobby Donnell and Lindsey Dole on The Practice.

I don’t think that qualifies. Though they were obviously in love (and had occasional lovers’ quarrels during their times in the White House), they never consummated BECAUSE they knew it was inappropriate. Amy asked Josh if he was dating Donna before they went out; he replied, “No, she’s my assistant.”

Major Nelson and Jeannie. (Of course, technically she was his slave and sexual-harassment policies would not apply; but they still milked the possibilities – she had to spend a lot of eps chasing him before she nailed him.)

Lois and Clark.

But Lois was not Clark’s boss, nor was he hers. They were equals, though Lois had seniority.