^^^ RE: whom gods destroy...was he really going to do her for his own pleasure or was it to enlist her aid in their effort to escape...? I believe it's the latter....?
Most likely, yes. Just as in quite a few other cases (although they mostly amounted to kissing, not sex).
He really fell in love 2 or 3 times, but the women (conviently for the show) had to die. He was even married as 'Kirok', when he had amnesia and did not know who he was. And there were cases when he fell for women because of weird outside influences... i.e. brainwashed in Dagger of the Mind, Elaan's tears, the woman in A Private Little War...Again no sex in any of those cases.. We also met some of his exes, and he didn't have the nicest experience with the one in Court Martial... And one of the women he had a relationship with in TOS turned out ot be a serial killer...
All in all, not very lucky with the ladies, all considered?
OTOH, he came off as a bit of a horndog in Wolf in The Fold... but then so did Scotty and McCoy.
He did do the comfort girl in Bread and Circuses, though...
Am I forgetting anything? He was portrayed as a ladies' man in so many episodes, but very few of those flirtations actually qualify as a relationship or a romance, and many did not even go further than the first base (or less).