Star Trek

Naw. I personally don't think he did. I think it's quite well established that he thought it was inappropriate to "go there" with his secretary (i.e. yeoman) even if he did have the hots for her for awhile. I find myself agreeing with the Kirk in "The Corbomite Maneuver" when he wishes that he'd been assigned a male yeoman. The captain having a female secretary was rather trite and painfully '60s of the show. I pretty much just find Rand annoying, and wish they'd just given Uhura and Chapel more scenes/lines instead.

Here's some info from Memory Alpha:

Yeoman was a Starfleet title with administrative and clerical duties. Starfleet used different rates of yeoman including "yeoman third class" as seen with Tina Lawton. (TOS: "Charlie X") Some yeoman, such as Janice Rand, were enlisted personnel during their time in this position. However, a yeoman could hold the rank of an officer, as seen with Martha Landon (TOS: "The Apple") and an unnamed yeoman assigned to the USS Enterprise-A, who wore an officer's uniform with the rank of lieutenant junior grade. (Star Trek V: The Final Frontier)

I agree with you starshipgalley.