Petracles

 
When they were "both very young" Xena and Petracles were engaged to be married. This seems to have been at a time Xena was not very experienced with men, so it might have been in her pre-warrior, teen-aged "punk" days. Petracles was a master manipulator. Having 'conquered' Xena, he lost interest in the quest and dumped her.

Xena having a talk with her old flame.

Many years later, Xena and Gabrielle meet Petracles again. They are forced to team up with him during an adventurous treasure hunt. He claims to regret his old ways. Xena is 100% cynical, certain he is still his old deceptive and manipulative self. He toys briefly with Gabrielle's affections, but they are too involved with their adventure for anything serious to develop.

Xena and Gabrielle comfort the dying Petracles

 
Petracles proves that he has at least some noble impulses though. He helps Xena and Gabrielle outmaneuver an evil competitor. But in the process, he is mortally wounded. As he dies, he reveals that he had kept his and Xena's betrothal bracelet all these years.