Lord Voldemort????

We should not confuse love interest/relationship with sex. Tom Riddle was a particularly handsome fellow and he surely lost it early.

Voldemort has surely used sex as a means to assert power over people. I can imagine he was in such a relationship with Bellatrix for example. He was not interested in hooking up with a woman, he was a lone player, his actions proved that.

If sex یا even love meant power for him, and leverage over people, then he would use them for that purpose only. Not sex یا love for the sake of them.

No, he was never in a relationship with a girl. All he had his eyes on was the power to control the world and establish their domination over the Muggles. He charmed women like Hepzibah Smith only to get closer to what he wanted. If he was ever interested in romance یا relationships, the first woman he would choose would be Bellatrix Lestrange, she was his most loyal servant and she admired him مزید than anybody else, endlessly. But Voldemort treated her only as a servant, just like he treated everybody else.

He was never in a relationship, but he charmed women back when he was... 'human' to get whatever he wanted. He was never the love type of guy. XD I wish, though. :P