If Trekkies talk about romance, they cannot leave out the absolute king of it: James T Kirk. He wasn't the only one on his ship getting flirty, mind you. He just was the one who did it the most. AKA one out of every 3-5 episodes or so.
While they sometimes helped steam up the moral dilemmas of space travel and alien contact, not all Star Trek romances left a great taste in everyone's mouth. Honestly, some were actually pretty terrible. It doesn't take a Kirk expert to know that.
Here are TOS's 10 Worst One-Off Romances.
James T. Kirk & Miramanee
Sure, Miramanee truly loved Kirk. They even were married and having a kid and everything. But, there is that whole awkward part where her tribe was based on Native Americans and Kirk was a white man they treated as a God. She basically fell in love with him because she thought this stranger was a God.
Yeah, that's kind of a gross relationship. And worse, the villagers stoned her. She lost her life because she loved Kirk. This relationship is just depressing, problematic, and bad all around.
Miramanee deserved a lot better than this.
Spock & T'Pring
Sometimes, Spock is just a little too by the book. He and T'Pring were betrothed since childhood, but he never spent any time getting to know her or trying to romance her. He just went off with Starfleet and never looked back. That is until he had to.
No wonder she fell in love with someone else.
Honestly, T'Pring deserves a lot of credit for choosing what was best for her in a rigid world like Vulcan. It's just what was best for her was not Spock. That relationship was doomed from the start.
Pavel Chekov & Tamoon
Consent is queen, guys. When the Enterprise crew was kidnapped for "The Gamesters of Triskelion," Kirk wasn't the only one dealing with some romance. It's just that he was the only one who wanted it.
Like Kirk had a trainer, Chekov also had one named Tamoon. Tamoon was immediately attracted to Ensign and similarly got pretty cozy while trying to train him.
The downside is, Chekov had zero interest in her and she didn't seem to notice that. Chekov deserved to have his rejections be heard so fans just kinda ignored the fact this aggressive flirtation ever happened.
James T. Kirk & Janice Rand & Miri
The relationship between Janice Rand and Kirk was already strange and undefined. However, it was at its worst when Miri got involved. A young girl about 15, Miri lived on a planet where all children were immune to a plague, but once they went through puberty they got infected and passed away.
Miri got a huge crush on Kirk the second she saw him and Janice was oddly jealous. Worse, though, was Miri's insane jealousy of Janice. She literally tried to end her life.
Fans get that Kirk is a hot commodity, but c'mon. This situation was really out of hand and gross.
Scotty & Carolyn Palamas
Once upon a time, Scotty had a crush on an archaeology officer named Carolyn. Unfortunately for him, before he could tell her how he felt, the Enterprise met a literal god: Apollo. He claimed that he once visited Earth and the people there, the Greeks, proclaimed him a god.
And the second he laid eyes on Carolyn, he fell in love with her and named her his future queen.
Scotty got a little riled over this, but Apollo was nothing but kind and generous to Carolyn. Even though he had a temper and was a snob to the rest of the crew, he treated her like a goddess.
However, when he threatened to destroy the ship, Carolyn saw his true nature and used her relationship with him to help the Enterprise escape. In the end, his essence was "scattered to the wind" and Carolyn was heartbroken.
What a dramatic end to what was supposed to be Scotty's crush?
Spock & Zarabeth
The Enterprise has had many time travel adventures, but few were as weird as when Spock, McCoy, and Kirk went back in time and started "reverting". Slowly, Spock had less and less control over his emotions, as early Vulcans were much more emotionally volatile. During this time, he met a woman named Zarabeth who tried to convince him that his reverting genetics meant that he couldn't go back. Romanced by her sweet words and beauty, he believed her.
The selfish lady just wanted Spock to stay with her forever and was lying to force him to stay.
Luckily, his crew-members forced him back and he became his old self again. Zarabeth disappeared from his mind like she never existed.
James T. Kirk & Drusilla
Kirk has a lot of questionable one-night stands, but few are as shady as Drusilla. For one, she worked for Claudius Marcus, a cruel games-master. Second, "work for" is a bold choice of words because she was his slave. Claudius "gave" Drusilla to Kirk the night before he planned on executing him.
So yeah, Kirk had a one night stand with a slave. Feels icky and it should. Kirk at first was wary, but he said it was just because he thought she was a spy.
Maybe he should be wary because, who knows, she's a slave, but fans choose to forget this relationship happened.
Christine Chapel & Roger Korby
Once upon a time, Christine Chapel was Roger Korby's student. They fell in love and even got engaged before he went on a mission and disappeared.
Years later, they found a distress signal that seemed to be tied to Korby. With Chapel in tow, Kirk went down to the planet to investigate.
It seems Roger left her to further his android research, destroy some local dormant aliens, and turn himself into one, too. Yeah, their romance ended worse the second time. The man she once loved was now only a pile of obsessive memories locked in a mechanical body.
Leonard McCoy & Tonia Barrows
During the episode, "Shore Leave", McCoy was trying to romance the beautiful Tonia Barrows. When the illusions started appearing, they found a gorgeous princess gown and she put it on. However, quickly things started getting out of hand. A Black Knight seemed to spear McCoy and Barrows felt horrible. Then, later, he reappeared like nothing had happened.
Instead of continuing his date with Tonia, though, McCoy decided to imagine two beautiful women, one on each arm. And when Tonia seemed upset? He just said, "After all, I'm on shore leave".
Yeah, this is just a sad case of a date gone horrible. Barrows deserved a lot better.
James T. Kirk & Lenore Karidian
Don't you love it when you fall madly in love with a murderer?
Kirk met Lenore Karidian by seeing her father's Shakespearean play troupe. There were some mysterious murders happening wherever they went. Kirk and co. quickly identified her father, Anton, to have once been a brutal executioner named Krodos. Suspecting him of the murders, they quietly investigated him while keeping up a friendly face.
Meanwhile, Kirk started getting very close to his daughter, Lenore. He fell head over heels. Kirk even thought he could settle down with her.
But, in the end, it was Lenore stabbing everyone to cover her dad's secrets and accidentally ended his life herself. She ended up in medical custody and the romance abruptly ended.