Geordi talking about getting more action in his good book than Wesley ever would get on his date with whomever in "Sarek" How old was Wesley there?
Picard revealing he wants to look cool for the children and dosn't want to make an ass out of himself in front of them. If I were Riker I'd have backed slowly out the room, never to be seen aboard the ship again.
Most of the times Riker tried to be "seductive," he came across as pretty creepy. TOS Scotty had a similar problem when wooing a lady, except he didn't come across so much creepy as just embarrassing.
TNG's episode "The Game." Or as the brilliant recapper Keckler of Television Without Pity fame noted: "Riker's dick endangers the federation." UGH
recently rewatched TNG ep Time Squared, the duplicate Picard lying on bed in sickbay and looking around in horror and confusion. Very creepy, as I dreaded the moment he would be looking straight into the camera (didn't happen, btw). Then again, I suppose it was intended as such. add: one which is definitely not intended as creepy but does give me the creeps in retrospect (of DS9 and such): [Wesley]: We're from Starfleet, we don't lie!
THIS! When I first saw this (I was a kid), I thought nothing of the scene other than one that was supposed to be humorous. But subsequent watches as I grew older lent the dialogue, his delivery of it, her reception of his "joke" and just the entire exchange a strongly cringe-y feel. Oh well. Scenes like this (and episodes like Turnabout Intruder) force us to place TOS firmly in its time and excuse it for what it ultimately was: a 60s TV series.