There are some good moments in the episode where Data is courting a woman on the Enterprise ("In Theory"
). Particularly when he goes to different people for advice about women. Worf demonstrates a roar, then says women throw things and men duck
, Picard says he'd be happy to give advice about women...as soon as he has any, and that rascal Riker tells Data the rewards make a relationship worth pursuing, putting on his big charmer smile and saying, "you'll have to find out for yourself"
when Data asks him to be more specific about the rewards.
There's also that hilarious moment where the lady is holding Data's arm like a couple while they're talking to people in Ten Forward. She asks him to repeat what he'd told her earlier when he saw her room and he says, "I believe you have an aversion to orderliness."
Some of my favourite funny, yet insightful romance scenes in Star Trek involve Guinan giving advice. One is when she tries to explain to Lal kissing and holding hands in "The Offspring"
, and another is when she and Riker are trying to give Wesley advice in the "The Dauphin"
as Riker simulates hitting on her to demonstrate how to woo a woman.
Guinan: [To Wesley]: "Shut up, kid."
Guinan: [To Riker]: "Now tell me about my eyes".