i don't think they would have seen much of each other the first half of her career, but depending on when he left the adf, maybe the second half when she was a pilot? she was actually a commissioned officer then so she wasn't as heavily on the lines as her role was to ensure her people didn't die. we could also mix it all together! they worked together for a stint, it got romantic, she remembered you're not supposed to fucking do that, and now just puts up with him because it's still a nice emotional connection to have to some degree. she deals with assholes all day everyday so it'd be nothing new for her!