I don't know that I think Joss was trying to show how problematic the trope was, but I DO think we're meant to see Xander as more flawed at certain points, and ultimately, he doesn't get with Buffy. He gets with Cordelia, but just like "nice guys" aren't all that nice, he screws that one up.
As stated below to tinny? I didn't pick up on it myself in the early seasons until now. I think I was too busy looking at other things, and at that time, Xander's behavior had been largely normalized by one too many teen movies and series of the time period. This aired in 1996-2003.
There are a few things worth keeping in mind while analyzing or thinking about the series as a whole, which we often forget?
1. Whedon wasn't the sole writer/collaborator here? Whedon didn't write 90% of the series, nor did he direct most of it. He may have punched up a bunch of scripts? But they couldn't film everything in the scripts and a lot got left out (no time). And he didn't start directing episodes until the later seasons - so most of the episodes were directed by someone who was not writing them. The writer often wasn't on set. Particularly in the earlier seasons. It's not a series like Fargo or True Detective, where there's mainly one director and one writer. Whedon wrote and directed at most a handful of episodes. Marti Noxon wrote most of the episodes with Xander in S2, or wrote for the character. And Whedon didn't write The Pack.
2. Whedon's main goal in writing the series was to subvert the slasher/horror film trope that he grew up watching in the 70s and 80s, also the teen romantic films by John Hughes, which normalized the incel trope. And to examine abuses of power, along with male toxicity.
3. He pushed often to the point of bullying - his writers and himself to write about their worst experiences, worst day, most embarrassing moments, things they regretted, biggest mistakes they made and stick fangs on it. He was writing a teen horror series and wanted to show how difficult it was to live in this world, but it was worth it.
So, upon re-watch of S1 and most of S2 now? I think he may have unconsciously gone there? I don't know. I know I didn't pick up on it until now, mainly because the incel trope had been normalized to a certain extent. But I'm really picking up on it in the rewatch - Xander is obviously depicting the behavior of the seemingly nice guy - nerdy incel, and even apologizes for it at times in an offhand sort of way. And he does get smacked for it - by various characters. The writers even examine why he feels that way in later seasons and how he became that way.
I honestly don't know how much of this was intentional or not? But they definitely did deconstruct his character over the series along with that trope, and it started with S1. The Pack is referenced several times in S2, with Xander, specifically in Phases, where it becomes clear to Buffy that Xander didn't forget any of it and just pretended to.
I think the writers felt the need to show both sides? And not demonize Xander? Which is also interesting. I honestly think that maybe Whedon was grappling with the behavior, as were the other writers. They loved how dark they went with the Pack, and that Brendon could play that well - but at the same time were hesitant to go too far with it. Yet, felt the need to deconstruct the trope - I think that may be why Jonathan, Andrew, Warren, and other characters were introduced - so they could do it without losing the Xander character completely.
Regarding Joss
As stated below to tinny? I didn't pick up on it myself in the early seasons until now. I think I was too busy looking at other things, and at that time, Xander's behavior had been largely normalized by one too many teen movies and series of the time period. This aired in 1996-2003.
There are a few things worth keeping in mind while analyzing or thinking about the series as a whole, which we often forget?
1. Whedon wasn't the sole writer/collaborator here? Whedon didn't write 90% of the series, nor did he direct most of it. He may have punched up a bunch of scripts? But they couldn't film everything in the scripts and a lot got left out (no time). And he didn't start directing episodes until the later seasons - so most of the episodes were directed by someone who was not writing them. The writer often wasn't on set. Particularly in the earlier seasons. It's not a series like Fargo or True Detective, where there's mainly one director and one writer. Whedon wrote and directed at most a handful of episodes. Marti Noxon wrote most of the episodes with Xander in S2, or wrote for the character. And Whedon didn't write The Pack.
2. Whedon's main goal in writing the series was to subvert the slasher/horror film trope that he grew up watching in the 70s and 80s, also the teen romantic films by John Hughes, which normalized the incel trope. And to examine abuses of power, along with male toxicity.
3. He pushed often to the point of bullying - his writers and himself to write about their worst experiences, worst day, most embarrassing moments, things they regretted, biggest mistakes they made and stick fangs on it. He was writing a teen horror series and wanted to show how difficult it was to live in this world, but it was worth it.
So, upon re-watch of S1 and most of S2 now? I think he may have unconsciously gone there? I don't know. I know I didn't pick up on it until now, mainly because the incel trope had been normalized to a certain extent. But I'm really picking up on it in the rewatch - Xander is obviously depicting the behavior of the seemingly nice guy - nerdy incel, and even apologizes for it at times in an offhand sort of way. And he does get smacked for it - by various characters. The writers even examine why he feels that way in later seasons and how he became that way.
I honestly don't know how much of this was intentional or not? But they definitely did deconstruct his character over the series along with that trope, and it started with S1. The Pack is referenced several times in S2, with Xander, specifically in Phases, where it becomes clear to Buffy that Xander didn't forget any of it and just pretended to.
I think the writers felt the need to show both sides? And not demonize Xander? Which is also interesting. I honestly think that maybe Whedon was grappling with the behavior, as were the other writers. They loved how dark they went with the Pack, and that Brendon could play that well - but at the same time were hesitant to go too far with it. Yet, felt the need to deconstruct the trope - I think that may be why Jonathan, Andrew, Warren, and other characters were introduced - so they could do it without losing the Xander character completely.