[DS9] Season 2, Episode 6 (Netflix: S2 E6): Melora
Bashir spends an episode romancing a visiting starfleet officer. It’s not a great episode, but given the premise I suppose it could’ve been a lot worse.
Read more at Memory Alpha
Notes:

They get a visit from a cartography officer that’s going to chart parts of the Gamma Quadrant. Her species is used to lower gravity

Bashir breaks through Melora’s attacking nature and gets her to go on a date. It may be the first time where Bashir actually seemed to know what he was doing while flirting.

Melora falls and can’t get up, but doesn’t tell anyone, because she didn’t want anyone to see her like that

Melora decides not to go with the treatment because she wouldn’t be herself anymore, or one of her own people. And a klingon sings, which probably didn’t need to happen.
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