[RIKER and GUINAN attempt to teach WESLEY how to flirt]
RIKER: You are the most beautiful woman in the galaxy. You don’t know how long I’ve wanted to tell you that.
GUINAN: But you were afraid. 
RIKER: Yes.
GUINAN: Of me? 
RIKER: Of us. Of what we might become. 
WESLEY: Uh, Commander— 
RIKER: Or that you might think that was a line. 
GUINAN: Maybe I do think it’s a line. 
RIKER: Then you think I’m not sincere. 
GUINAN: I didn’t say that. There’s nothing wrong with a line. It’s like a knock at the door.  
RIKER: Then you’re inviting me in. 
GUINAN: I’m not sending you away. 
RIKER: That’s more than I expected. 
GUINAN: Is it as much as you hoped? 
RIKER: To hope is to recognize the possibility. I had only dreams.
GUINAN: Dreams can be dangerous. 
RIKER: Not these dreams. I dream of a galaxy where your eyes are the stars and the universe worships the night.  
GUINAN: Careful. Putting me on a pedestal so high, you may not be able to reach me.  
RIKER: Then I’ll learn how to fly. You are the heart in my day and the soul in my night. 
WESLEY: I don’t think this is my style. 
GUINAN: Shut up, kid! 
[turns to RIKER] 
GUINAN: Tell me more about my eyes.

2.10 | The Dauphin

From The Dauphin, aka the episode where Wesley is about to finally get some, but ends up being cockblocked by the lamest monster ever. Poor kid.