Lieutenant Commander Geordi La Forge programs an awkward enough beach rendevous on the holodeck, complete with Coco-No No cocktails and a gypsy serenade.
When his date shows she is clearly not impressed with coconut rum or violinists in pirate boots and puffy shirts, he retreats to Ten-Forward with his visor downcast.
A romantically inept android isn’t exactly a walking encyclopedia of love either, but Riker gets extra credit for his literary seduction skills. He ignores all the warnings about what this teenage head-of-state crush has been hiding.
Moment of epic awkwardness: When Wesley finally works up the nerve to kiss Salia, her governess seems to materialize in the doorway and morphs into something that could pass for a cross of Mothman and Bigfoot.
He then escapes to a Dick-Tracy-esque program on the holodeck to make himself unavailable.
Lwaxana pursues him, enters the program and starts seducing a mystery man who turns out to be no less holographic than the rest of the program. Moment of epic awkwardness: When Lwaxana starts making bedroom eyes (and suggestions) at dessert, Picard eagerly invites Data to interrupt their disaster date with sleep-inducing scientific anecdotes.
En route to the Pacifica conference as the representative for Betazed, she lures him into what is supposed to be an ambassadorial dinner for the crew (to which she only invites the mortified captain).