At first I thought this thread was titled "Janeway's Cougar Hunt" and I got super excited.
Anyway.. the only appeal of Jake for the dabo woman is that he is the station commander's son. There is no way she would be looking at him if he was just some teenager whose dad was cleaning conduits or something. This is what makes it a bit unbalanced and I'm pretty sure Sisko knew that. Sure he's a nice kid and she enjoyed talking to him but it's not like there weren't other adult men around.