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The 100th episode of a television show is typically a major milestone, but since "Brooklyn Nine-Nine" is anything but a conventional cop show, the series celebrated an episode early.

Its 99th installment sees Detective Jake Peralta's (Andy Samberg) "Die Hard" obsession screw up an opportunity for Captain Ray Holt (Andre Braugher) to interview to be the New York Police Departments' new commissioner, only to find out that Holt is self-sabotaging because of a deal he cut with a mob figure to get Jake and Rosa Diaz (Stephanie Beatriz) out of prison earlier this season. Oh, and Rosa came out as bisexual to Charles (Joe Lo Truglio), adding a new dimension to what is already one of the most thoughtfully diverse shows on network television. And there was an exploding recreational vehicle.

In other words, "Brooklyn Nine-Nine" marked its achievement in a big way. I hopped on the phone with showrunner Dan Goor to talk about Jake's and Holt's respective evolutions, how marriage might change Jake's and Amy Santiago's (Melissa Fumero) relationship, and how a fundamentally nice comedy can tell stories about subjects like police racism and sexual harassment (a subject that's affected cast member Terry Crews personally).

Q: I sort of felt like the dynamics of the show have shifted in a really interesting way. When the series started, Jake was this kind of talented screw-up and Holt was the obsessively rectitudinous person who was trying to get him to live up to his potential and to behave better. And now we've reached this really interesting point where Jake is the person trying to protect Holt from having done something bad. What did it take to get there, and what does that reversal let you do both dramatically and comedically?

A: Thank you for noticing that that is definitely the arc of the show. ... I mean that totally seriously. Right from the beginning we realize that the dynamic of the show was Holt and Jake, and our idea was to incrementally mature Jake and to also loosen up Holt a bit. I think it is of note that the quote bad thing unquote that Holt does is in the service of a greater good. And although Holt himself may say the never justify the means. I think he was able to do a sort of moral gymnastics that made it justified at every point, although certainly the pilot Holt would not have probably made that deal with Seamus, and not have destroyed the RV in order to sabotage their trip back to New York.

Q: It seems to me like Jake is definitely a better cop than he was at the beginning of the show. Not necessarily because his moral compass was out of whack, but because he is more disciplined and has a better sense of the full spectrum of what it takes to do the job. Do you think Holt is a better cop at this point in the show than he was at the beginning?

A: That is a great question and I would say yes, I think he is a better cop. I think that the lesson that he taught Jake in the very first episode, which was that we're a team and we do everything better as a team, it's a lesson that he was able to speak but not really live until the show progressed. I think that that his journey has been as a person who was never allowed on the team learning to trust the rest of the team, and that they truly have his back, and and that this episode is another step in that direction. He certainly trusts them more than he did before. And I think the more he trusts them, the better he is as a cop.

Q: I also think back not just to the idea of teamwork from the first episode, but to that emphasis on this procedural focus, and the idea that if you do everything right you'll achieve the right outcome, which is sort of Holt's mantra. But it also seems like one of the things that he's learned over the past couple of seasons is that that's not always the case. ... And so it seems like the shows felt a little bit more confident in the last few years making the point that things sometimes go wrong, that Terry can be stopped by another cop who is probably a racist, that you can do all the right things and still end up wrongfully imprisoned. How do you think the show's vision of how the justice system works has changed over time?

A: I think that at the end of the day, we're still a goofy comedy that isn't making gigantic points all the time about the justice system. But I think that you know we also live in in the world that exists currently.

And as writers, and actors, and as a result I think we have, as a show, been more willing and interested not even willing more interested in addressing those issues and problems the justice system has, the inherent unfairness and biases, and the fact that you can do everything right and the wrong outcome can still occur. ... We weren't really focused on that in the first season. We were really thinking of this more as an office place comedy that where some of the stories and a lot of the fun derived from the cops setting.

And I think that as the show matured and as the world changed around it we saw an opportunity to address these social issues and change the attitudes of the characters accordingly. ... I felt like by the end of season two, or certainly in season three, Black Lives Matter was becoming such an issue in media. And other television shows had talked about police brutality and police relations with the African-American community . ... We wanted to as well. We just felt like we couldn't until we had figured out exactly how to do it right correctly for our show. And so it wasn't so much an awakening as a struggle to do it in a way that felt sincere and good.

Q: A lot of your work is nice without being soft. And I feel like that's a tone that has managed to establish very early and have been able to hold onto even as some of the underlying issues and character dynamics have changed a lot. This is an era when a lot of TV, especially prestige TV that gets a lot of praise gets that in part for being sort of mean and unflinching.

A: I would say it's hard to make television shows where the characters are friends, are good people who are well-intentioned and act rationally and who talk to each other about their decisions and their problems, because it makes it very difficult to generate conflict, and without conflict it's very difficult to generate stories and tension and comedy. And so a lot of the time, that's why we have big evil characters come into the world. ... But I just think that, I think to some extent we can, I run into model a police force that a group of people who are on the police that were the, the kind people you'd want to be on the police. And I think that it's also a reflection of the people we work with and spend time with and the world. It just felt sincere to the world we know now.

Q: We've talked about the overall diversity of your cast and it seems like that's giving you a lot of wiggle room in that no one ever has to stand in for their entire community. Everyone gets to be idiosyncratic to a certain extent, and people get to have disagreements and behave badly without necessarily feeling any sort of requirement to be noble . ... And it was interesting to me that in this episode you have Rosa coming out to Charles when he finds out she's dating a woman, because that's an area where you haven't necessarily had two people in the core cast who represent the community you have. You have Kevin of course, you have Holt's exes, but you don't necessarily have another non-straight cop. And I was curious you know what you felt comfortable telling me about how that was going to play out, and whether there were opportunities that gave you beyond sort of just this storyline?

A: Going forward I think it's going to give us a lot of stories. And also it would be fun to see Rosa dating. It'll be fun to see Rosa dating ladies. It'll be fun to see Rosa dating men. ... We decided the very beginning of the year that we would have Rosa come out as bisexual. And then they were in jail, so it wasn't really the right time to do it. And then we wanted to make sure that she broke up with Pimento (Jason Mantzoukas) first, and we got pushed and pushed and pushed, and then when it finally when we were breaking that episode it was it seemed like such a good, interesting tidbit to throw in that we will explore more in the next episode.

Q: I can't decide if I want to say thank you for not doing the "Brooklyn Nine-Nine" lesbians-in-prison episode or that I'm really sad that I'm not going to get to see the "Brooklyn Nine-Nine" lesbians-in-prison episode.

A: We didn't want to make Rosa come out in prison, because there's such a TV and film trope of being bisexual in prison, and we didn't want her to do it before breaking up with Pimento or as a way of breaking up with Pimento because we felt that muddied her character's intentionality. We just wanted to make sure that her decision to come out was not a reaction to anything else, but because it was something she needed to do for its own sake, for herself.

Q: It also seems like an opportunity to do that sort of a intergenerational story and that's come up in earlier seasons when Holt is kind of giving up control of this organization for LGBT officers that he founded. But it seems like this could be a place where you've got the generational and gender split on the issue. Is Rosa the first non-straight female character on the show?

A: I think so, yes.

Q: It seems like they just have a lot of differences and perspectives and styles that could open a lot of fertile territory.

A: That does seem like an exciting thing to explore. I like that as an idea, as a way of going forward.

Q: Characters getting married is a big step. And one thing I admire about the work that you and Mike (Schur) have done is really treat that as part of the ongoing story of our relationship. The idea that you get married but there are still a lot of adjustments and arguments it opens up, having kids, it opens up all family stuff we saw in the Thanksgiving episode this year. So what do you see as the ongoing issues for Jake and Amy as they start moving forward into this new phase of their relationship?

A: I think that the ongoing issues are ultimately, ultimately a lot of the ongoing issues are the fact that they are very different personalities and so are very naturally an odd couple I think and it will be fun to see that play out. There's there are aspects of that that will play out in wedding planning and the wedding itself. And then in them being a married couple.

A: It seems like it really creates some space for them to start digging into some of those areas where their differences are not necessarily idiosyncrasies, like seeing the two of them raising kids would be both really funny and really stressful because it doesn't necessarily seem like they have some of those basic disagreements worked out in a way that you might have to be to be parents.

A: It's so interesting, I can't tell if I want to see them raise a kid or not. ... I guess the interesting thing would really be that Amy is so career-driven and so is Jake, and they are not super wealthy so a nanny is a difficult thing. ... They don't have that many options and maybe it would be good because it would be an interesting stress on their, on their life.

Q: They could do a nanny share with Charles.

A: Charles just instantly retires and becomes a nanny for both of them. He becomes their au pair!

Q: You've hit this milestone, and TV is a sort of an unpredictable landscape right now. I'm not going to ask you to speculate on how many episodes you have left, but I would be curious if there are points you'd like to make about policing or some things you'd like to do now that you've gotten this far.

A: I want to make sure that we make sure that all of our characters are heading in a direction or a place in their life where, if you never saw them again, you would be happy that that's where they were. Is that too bleak? That's pretty bleak.

Q: Is there anything specific about policing you want to say that you'd like to try and take a stab at?

A: I think we could really explore the the experience of female cops, especially in a leadership position, and also Latino cops, and that's something I would like to do. I think that it could be interesting to look at all of this sexual harassment stuff and see if there's a story in (it for us) or if it's so horrific that it's hard to translate to a comedy show. ... There are two areas I'd love to explore, but I think they're just kind of too dark for our show. And one of those is Jake having to commit an act of violence justifiably and then deal with the repercussions of that. But I just don't see a way to do it. I just don't know. ... Also I think it's probably too hard to do is really dealing with one of your compatriots being hurt in the line of duty and dealing with that.

Q: Other than Charles getting shot in the butt.

A: I mean that's that's the way we dealt with it. We made it.

Q: When it comes to sexual harassment that's an issue that I know Terry Crews has been dealing with personally. The cast has been amazingly supportive of him publicly. That's something I think been a really awesome example. ... I imagine that might be something that comes back as a creative conversation. Are you there yet?

A: We are not there yet. We're really just in the 'Hey, this will be a thing we should talk about.' ... We want to make sure we're really telling the right story and not just reacting to the fact that it's in the news right now.

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