Best of/Worst of Character Moments
Never Kill a Boy on the First Date
Best Character Moment:
Buffy: I think Buffy's finest moment is when she gives up her budding romance with Owen because she instinctively understands that she'll get him killed due to his penchant for wanting to throw himself into danger. Since she really likes him, it was a very adult thing for her to do.
Xander: I'm afraid that Xan isn't shown in the best light throughout this episode, so 'fine moments' from which to choose his best are very few. In fact, I think I have to go with 'no entry' here. I was tempted to list his following Giles as a good moment, but that was actually Willow's idea - Xan was too focused on his jealousy, so he doesn't even get that little thing.
Willow: Will is also a difficult one to find a 'fine moment' for. She basically plays the supportive best friend to Buffy's dating efforts. She does decide that they have to watch Giles' back, while Buffy is out on her date. As little as it is, it's more than Xan gets for good character moments. I'll say her best moment is in being concerned enough about Giles to provide him backup after he goes off to the mausoleum alone.
Cordelia: The cheerleader doesn't get any fine moments, at all. She's too obsessed with taking what Buffy is clearly interested in. Though her self-absorption and catty comments remain entertaining, they're hardly 'fine moments of character'. No entry.
Giles: I'm afraid the Watcher also isn't given many fine character moments this episode. It's all about Buffy's dating life and how Slaying interferes and setting up the Annointed One/Prophecy Girl's plot. Even when Giles faces the vampires, he's ineffective and can hardly be said to have a fine moment. I'll give him a nod for his sincere sympathy toward Buffy when she has to protect Owen by breaking up with him, even though she really likes him. He could have been relieved that this complication was forestalled and may even be, but he doesn't express it. Instead, he acts to be supportive of her.
Worst Character Moment:
Buffy: Well, her attempt to lie to Owen about why she didn't show at The Bronze was not only painfully inept, but it made her sound like a stupid ditz. How fortunate for her that Owen humored her... or is just as dumb himself, depending on how you feel about him. She really needs to develop some sort of deception ability to help her with these 'hiding my Slayerhood while pursuing normal life things' moments.
Xander: Xan has a lot of bad moments in this episode, all of them related directly to Buffy & Owen's attempt to go on a date. I'm going to list his worst moment though as in Buffy's living room, where he tries to sabotage this budding romance by misdirecting Owen about Buffy. Sure, his desperation is a bit amusing, but his lies about Buffy's not wishing to dance, or be touched just makes her look worse after her "we have no clocks" excuse previously. There is trying to win Buffy's attention, and then there is this... actively trying to drive a rival away with weird tales about your friend.
Willow: Willow is the supportive best friend throughout and doesn't have any bad character moments to choose from. This is a good thing.
Cordelia: Well, Cordy is selfish throughout, of course. Her worst moment, to me, though is her determined 'break in on Owen & Buffy's dance'. It doesn't work and Buffy gets in a nice zinger on her over it, but it is pretty rude.
Giles: Giles gets the worst of the bad character moments. You might think it would be Xan's deliberate attempts at sabotaging Buffy's dating attempt, but when Giles... trained Watcher... goes to the cemetery and nearly gets caught unawares by vampire minions... well, that's just incompetent. He doesn't even have a stake in easy reach!
Good thing the minion vampires weren't as bold as Borba, or Giles would have bought it right there. His humiliation continues as he flees and then locks himself in a room with no escape, and still he hides in a cadaver locker rather than slay. He's so much better than that in S3.
As you can see, no one really shows us the best or worst of humanity in this episode. Their triumphs and shortfalls aren't all that good or bad, so there wasn't much to work with for this listing.