McCoy was the emotional one, Spock was the serious and logical one, and Kirk was the dashing adventurer who swept the ladies off their swooning feet. Kirk of the original Star Trek series has a reputation for being really smooth with the ladies, but if you pay attention to the original series, that doesn't really ring true.
Kirk liked to chase women, sure, but that doesn't mean that he was good at it. In fact, there were plenty of times when he was absolutely terrible at it. Here are ten times that Captain James Kirk tried to impress a girl but fell flat on his face instead.
Lenore Karidian
Initially, it seems that Kirk really likes Lenore, but all it takes is one little murder of an old friend for everything to fall apart. He instead ends up using her in his criminal investigation, which she understandably resents. Things were doomed to go sour with these two anyway, but in the end, Lenore is deeply disillusioned and she makes sure Kirk knows it.
The Priestess Of Yonada
The best thing about this rejection is that Kirk loses to McCoy, which happens a lot more in Star Trek TOS than anyone wants to admit. Nitira all but ignores Kirk in favor of the more sincere and intuitive Dr. McCoy.
The High Priestess of Yonada isn't impressed by Kirk's manipulative tricks, either. She catches the Captain and Spock in her inner sanctum later on, and only her love for her people, and McCoy, saves Kirk from execution.
Eleen, Regent of Capella IV
When this episode starts, this young queen and her unborn child are at the center of an interstellar conflict over mineral rights and planetary sovereignty. By the time it ends, she's the acting regent of her people. Throughout the episode, she openly rejects Kirk, favoring only McCoy, despite his attempts to get to know her better. Although her son is named after both of them, Leonard James, Kirk's name was probably more of a tribute to Starfleet than a reflection of her own personal feelings.
Elaan Of Troyius
She falls for him eventually, but it has nothing to do with this rather lame attempts to impress her. Kirk intends to teach Elaan about the culture of her future in-laws, but what starts out as a My Fair Lady parody becomes a retelling of the old Tristan and Isolde legend instead. At the closing of the episode, she quietly and sadly reminds him of how helpless he really is with a single, sad line.
The Romulan Commander
Kirk doesn't stack up very well against his female colleagues, either. There aren't any female Starfleet Captains in Star Trek TOS, but other races did have them. The unnamed Romulan Commander brushed Kirk off as impetuous, foolish, and maybe even mentally unfit for leadership.
Kirk might have thought that his bravado would impress her, as that would be one way to accomplish his covert Starfleet mission. She barely looks at Kirk long enough to toss him in her ship's brig and spends the whole episode flirting with Spock instead.
Amanda Grayson
It's easy to tell that Amanda sees the human in Kirk, which is why she connects with him on a casual level, but it's more nostalgia than genuine interest. As an intellectual and an ambassador for humanity, she's spent most of her life with men who tend to be more sophisticated. This is the woman who's a direct descendant of Arthur Conan Doyle, after all. Her opinion of him improves when he helps save her family's life, but that's a pretty high bar.
Miranda Jones
Kirk really went after Miranda. We're talking state dinner with full dress uniform, and the other officers followed suit. She wasn't impressed, at least not with him. Miranda had a similar background to another human who spent an extended timer with Vulcans, Amanda Grayson. Plus, Miranda can read minds. No wonder she was bored with Kirk.
Shahna Of Triskelion
This actually starts out rather sweetly, but of course, Kirk blows it. Shahna has been a slave all her life and is captivated by Kirk's stories of life among the stars. Instead of having faith in her ability to see beyond the confines of her cage, he knocks her out and tries to escape.
Naturally, this doesn't turn out so well. He ends up facing her in a freestyle match and she's not happy about his behavior. At the end of the episode, she has her freedom, not only from the gamesters, but from him.
Droxine And Vanna
Still not a believer? Try this one. Kirk is so bad at this that there was this one time when he messed up with two women in one episode. Droxine, a sheltered but cultured and artistic woman, looks right through Kirk and only has eyes for the cool, intellectual Spock. Vanna, the crafty rebel, easily fools Kirk because he thinks that he's fooling her. The resolution at the end of the episode has more to do with Spock and Scotty's efforts than Kirk.
Mother Horta
A shout-out to the non-humanoid characters on this list, Kirk's general buffoonery with women even extended to non-carbon based life forms. In yet another instance where Spock steps in to save the Captain from himself, the Science Officer mind-links with the Horta and discovers her true nature and intentions. That includes her low opinion of humans, in both behavior and appearance, partly because of her impression of Kirk.