It could be that he hasn't gotten her on a date yet, because he hasn't gotten a clue that she wants to call the shots where that is concerned. So now he's stuck still trying, and thinking he's getting somewhere until she brushes him off again. He would be so very confused, but would still try again.
Then that would definitely give them a more positive relationship. :) As long as Juno is handled by someone else officially, they'll get along just fine. And Lucas resents that sentiment, thank you! Lol.
I would say it's discouraged, but not entirely disallowed. There are limited dating possibilities in their line of work, particularly for the supers, so I would think those who could report it would generally turn a blind eye. At worst, there would be a reprimand and a change of handlers for the super. To use my characters as an example, Cassidy and Lucas dated briefly after she arrived at the program as his handler. She ended it, and to avoid damaging their working relationship, she requested that he be given to another handler. So as long as they can still work together, whether they're in a relationship or not, there wouldn't be an actual problem, I think. Cassidy would be a hypocrite to admonish either of them for dating, although Lucas would need to talk to Juno or Hollis or both to determine whether he should back off on trying to get anywhere. And would pout like a little boy if Hollis succeeded where he had failed, of course.