Shara Jenn, codenamed "Watcher Two", is a female human Imperial Agent of the Imperial Intelligence, a branch of the Imperial government of the Sith Empire. She later becomes the head of operations in intelligence, code-named Keeper, after her predecessor is made Minister of Intelligence. After Imperial Intelligence was disbanded, she was one of the former members who went rogue, and was eventually captured by the Republic.
Due to the lack of a Codex on her, little is known about Watcher Two's life before the agent meets her. Her real name is Shara Jenn, and she tells the agent that she was genetically engineered to be an intelligence officer, with all the desired traits that entails. She serves as the agent's handler during his/her missions: the person responsible for general mission information, where to meet the contact and the person the agent reports to when the mission is completed. She, along with the Minister of Intelligence, were branded rogue when Imperial Intelligence was disbanded, and was subsequently captured. Later both she and the Minister of Intelligence escaped Republic custody.
The agent first meets Watcher Two/Shara Jenn when he/she arrives on Dromund Kass and reports to imperial intelligence headquarters for the first time. This first meeting is a part of the imperial agent seeing the inner working of intelligence: the staff, code names, and procedures of the organization. Throughout the Agent's first duration on the capital planet Watcher Two communicates with the Agent during missions a handler, and with the other agents during mission briefings and debriefings.
At first she is distant from the agent, due to the fact that most of her agents end up dead soon after first meeting them. However she is not necessarily cold towards the agent if he/she does not disrespect her or her actions. If romanced by a male agent she opens up, showing a sign of trust and genuine affection rather than seeing a simple fling. Due to her genetic modification she exhibits an advanced intelligence but uses it in limited ways, staying focused on mission objectives most of the time. It is rare when her stoic persona cracks, and when this happens it is usually because of romantic actions.
Watcher Two, Shara Jenn, is a minor romance option but one that can be carried through the entire game. Even alien male agents can romance her, despite her vocal disdain for them when she first meets the agent. However, an alien agent cannot continue the romance further beyond Dromund Kaas.
The first chance for a romantic action with her is during the first meeting, where a male agent can say "sure thing, beautiful." To which she replies to not call her that again. Every future romantic or flirty gesture with her she increasingly responds to with interest, resulting in the agent and her kissing before he has to report to his star ship for the first time in the game. Keep in mind however that to keep the romance going no criticism of her or her actions must occur, for example when she mentions torturing a colleague. If this is done, the agent can perform a "side quest" during the mission Darth Zhorrid Arrives, titled "Watcher Two Relationship." This is where a male Agent can kiss her for the first time, cementing the romance (though this can be overruled by romancing a companion, Kaliyo or Raina Temple).
To keep the romance going while away from Dromund Kass simply select the flirt option with her whenever available and do not criticize her.