Robin's travels across the Mushroom Kingdom do occasionally bring her across the lands that Bowser has dominion over. Said areas are not as hostile as one may think, the locals normally being fairly sociable when a conflict is not currently underway (and if you don't happen to be a plumber).
One trip into these lands lead to her encountering a royal armored koopa who went by the name of Silas. Silas had worked extremely hard to bolster his rank, hoping to eventually attain enough trust from Bowser that he'd be able to be Bowser Jr.s personal body guard. The truth to this was that Silas had grown very fond of the maturing prince of Koopas and wanted to attempt to court him, but the process of doing so was very slow and occasional sieges by the Mario brothers often set things back months at a time.
It was through these moments that Silas would attempt to relax and forget about his sorrows in local hot spots where drinks and food and other social gatherings took place. In one such place, he caught Robin's attention, who was rather interested in Silas' plight.
Namely how Silas' pining was towards a target that didn't even know he existed and his needs were growing out of control to the point he was growing emotionally unstable, prone to snapping and getting sloppy in his work.Robin had a simple solution; date her.
By dating her, Robin was treated with respect as others saw her with a heavily armored elite koopa, and Silas was assured an outlet for his pent up desires towards junior.