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It should have been easy.
His father had been easy.
A being’s most intense emotions were almost always tied to a romantic partner. Threaten the partner, terrify your target, then provide a quick solution by way of the powers of the Sith. That formula had worked perfectly for Anakin Skywalker. Everything had been perfect until that damned Kenobi had cut off Anakin’s limbs and left him to burn on Mustafar. Kenobi would have made a fine Sith himself if he’d been given the proper guidance, but he hadn’t been worth the effort when Anakin was around.
Now, there was another Skywalker.
Younger. Not slowed by forty added kilograms of life support suit. Crackling with the power of the Force, just like his father.
Palpatine wanted him, and what he wanted, he would get. He just needed to find out who would be the person to threaten to make Luke admit that his Jedi powers were too weak to save them.
Anakin had been easy. Palpatine had seen his pathetic crush on Padme Amidala since the first time he’d met Anakin when he was just a small boy. He’d had years to gain Anakin’s trust, and manipulating him to fear for Padme’s life had been all too easy. He wouldn’t be able to gain Luke’s trust before the threat, but it should still work out the same way.
The trouble was, Luke didn’t seem to have any current romantic partners.
Or exes.
That couldn’t be. His intelligence probes must have just not been thorough enough. He’d make a note to have them destroyed later for their incompetence.
Unable to find an existing partner, Palpatine sent a spy to infiltrate a Rebel mission, one of his younger members of the ISB, a very attractive young woman who had been trained in the use of seduction for information extraction. In addition to the rest of her mission, she was also instructed to seduce Luke Skywalker.
She failed.
Palpatine killed her.
Days later, he realized that perhaps he shouldn’t have sent a woman.
The next mission Luke was on, Palpatine made sure he crossed paths with another ISB officer. This one was a young man, similarly trained and also instructed to seduce Luke.
He failed as well.
Palpatine didn’t kill him. He just demoted him to sanitation duty. He was beginning to think that the problem was in Skywalker rather than his officers.
Maybe Luke just wasn’t into humans. Or perhaps he was interested in the types of humans that the Empire considered unfit for service. Disgusting, but Palpatine would exploit that weakness if that was the case.
Having very few nonhumans or even much variety of humans in the ISB, Palpatine contracted out with mercenaries to hire various beings to try and seduce Luke. A Twi’lek woman. A genderfluid human. A Nautolan man. An agender Mon Cal. A Zabrak woman. A Devaronian man. All failed. All reported back that while the target was very friendly with them, he shied away when they tried to make things physical.
After months of reviewing the reports from these contractors, Palpatine had an epiphany.
Luke’s weakness did not lie in a romantic or sexual partner.
Luke’s attachment to his close friends was just as strong as a romantic attachment would be. That’s where his weakness lay.
Oh.
This was going to be very easy.