Rachel Bloom Gives us Some Not-So-Crazy Advice

The "Crazy Ex-Girlfriend" co-creator and star teaches us the fine art of making a musical before solving our listeners' dilemmas on "Google stalking" romantic partners and more.

(Photo Credit: Frederick M. Brown/Getty Images)

Rico Gagliano: Each week, you send in your questions about how to behave, and here to answer them this time around is actor, writer, and musical number belter-outer Rachel Bloom. A few years back, she set the Internet ablaze with a heartfelt and highly vulgar musical tribute to the late…

Brendan Francis Newnam: You can talk while he’s doing this, too. It’s totally Ok.

Rachel Bloom: Oh, I can?

Brendan Francis Newnam: Yeah.

Rachel Bloom: I’ll give sound effects.

Rico Gagliano: OK, that would be fun. She set the Internet ablaze…

Rachel Bloom: [Makes tiny explosion sound effect.]

Rico Gagliano: …with a heartfelt and highly vulgar musical tribute to the late sci-fi author, Ray Bradbury.

Rachel Bloom: Oooooh.

Rico Gagliano: She also put out a couple of albums of musical comedy.

Rachel Bloom: Oh!

Rico Gagliano: And then…

Brendan Francis Newnam: I didn’t know that.

Rico Gagliano: She teamed up with Aline Brosh McKenna to create “Crazy Ex-Girlfriend.”

Rachel Bloom: Ha!

Rico Gagliano: It is a musical TV series. It’s one of the most acclaimed and binge-watched in all the land.

Rachel Bloom: Oooooooooooooh.

Rico Gagliano: It stars Rachel — my sidekick here — as the irrepressible, romantically delusional Rebecca Bunch, who… well, let’s let the theme song tell the story.

Rachel Bloom: Oh.

Brendan Francis Newnam: It’s great that that does all the explaining for us. Saved us a lot of work.

Rachel Bloom: It does. Exactly.

On the recent resurgence of musicals

Brendan Francis Newnam: So, today, the Oscar nominations came out.

Rachel Bloom: Oh, right, right.

Brendan Francis Newnam: “La La Land” had something like 14 nominations. “Hamilton” still is ringing in everyone’s ears…

Rico Gagliano: All these musicals, and you have a musical TV show…

Brendan Francis Newnam: You studied musical theater, to a certain extent. What is going on?

Rachel Bloom: Every time there’s something new in musicals, like, “Is this the return of the musical?” And I like to think it is. I hope it is. I mean, they’re two great works of art. I mean, I think “Hamilton” did what musicals used to do and took show tunes and made them sound like pop songs. Because show tunes used to be what pop music was.

Rico Gagliano: Yeah. It’s like a popular songbook, basically.

Rachel Bloom: Yeah, and then I think a lot of people have a love for musicals. It’s just a question, will anyone make it? And, of course, Damien Chazelle had already made “Whiplash.”

Rico Gagliano: The “La La Land” director.

Rachel Bloom: Exactly. He tried to make “La La Land” before “Whiplash,” but no one cared. But now, he made “Whiplash,” and so they’re like, “Oh!” And then, of course, he has two A-list celebrities in it. And then, as far as my show, I mean… I’m still amazed that we get to do it.

Brendan Francis Newnam: You’re making songs and A-list celebrities, eventually, right?

Rachel Bloom: Sure.

On balencing mental illness and comedy in the show

Brendan Francis Newnam: So, I want to talk about the show for a second. Your character, Rebecca, suddenly moves across the country to stalk her ex. She quits a job, a high-paying job, moves to West Covina, all of which is funny, but at the same time, she’s dealing with mental illness.

How do you calibrate those two types of zaniness in the show: one that’s amusing and one that’s born of a real desperation there?

Rachel Bloom: The two have always been pretty together, part and parcel… is that the right way to use “part and parcel”?

Brendan Francis Newnam: Sure, we’ll say so.

Rico Gagliano: Well done.

Brendan Francis Newnam: The public radio audience will correct you, either way.

Rachel Bloom: There you go. The two have always been pretty part and parcel to me. With wackiness comes inherent sadness, I think. You need that to counterbalance the wackiness, and so — I don’t know, it was always kind of inherent in the show we were wanting to do because the premise is so wacky, to make it real, you have to deconstruct it and say, “OK, why would a woman actually move across the country?”

Rico Gagliano: But why make it real? It’s a musical. Typically, I think of musicals as being escapist.

Rachel Bloom: Yeah. Well, you want to have, also, a contrast to when the musical numbers happen. And so, there’s musical numbers to escape from what you need something to escape from.

Brendan Francis Newnam: Well, that’s a question. There’s one or two songs per episode. How do you know when to drop a song in?

Rachel Bloom: The best songs come from the emotional high and low points of the episode. It’s like how you write any musical. It’s like, when is the emotion too strong for the character to merely speak? When do they need to sing?

On how the Frankie Valli-esque Santa Ana winds character came about

Rico Gagliano: But there’s also a wonderful example of a magical character that you just kind of pull out of thin air to sing songs who embodies the Santa Ana winds, which we get here in Los Angeles every now and then.

Rachel Bloom: True.

Rico Gagliano: Where did that come from? He becomes like a narrator for the show.

Rachel Bloom: Yeah, we were talking about a structure for that episode. We had a lot of different structures, and we were thinking of genres we hadn’t done. And we hadn’t done Four Seasons, Frankie Valli. And we were talking about how, like, [imitates Four Seasons harmony] “Weeeeeeeeee,” it sounds like winds. And we were like, “Oh! We can have that keep coming back, and the Santa Ana winds are making everything weird.”

Rico Gagliano: Well, as we mentioned before, you came to prominence with a song called “Fuck Me, Ray Bradbury,” which we decided qualifies you to tell people how to behave, for some reason.

Brendan Francis Newnam: Are you ready for these questions?

Rachel Bloom: I’m so ready for it and how I’m going to… you have no idea how ill-equipped I am to answer etiquette questions. I’m so excited.

Rico Gagliano: We have some idea.

What are the appropriate limits of “Google stalking” before a date?

Brendan Francis Newnam: Our first one’s from James in Austin, Texas, but we actually got a number of questions on this topic. His question is: “What is the appropriate level of Google stalking before/after a first date? Should it be limited to just the online profiles publicly available about the date? Should it include obsessively skimming all of their friends and LinkedIn business contacts?”

Rachel Bloom: Here’s the thing: it’s all public. I think what you do when you over-Google someone is…

Brendan Francis Newnam: Over-Google.

Rachel Bloom: Over-Google. The thing is: you don’t want to be weird and be like, “I Googled you.” So, when they tell you a fact about themselves, like, “Oh, I work here, my mom’s name is this. These are my friends. I’m interested in this.” You then have to fake surprise. Which is not only hard to do, but also, you want to learn about this person in the context of a relationship, right?

I mean, I think the best way to go about doing it is to have a friend Google them, and just be like, “You let me know if there’s anything I should worry about.”

Brendan Francis Newnam: Give you a dossier? Hmmm.

Rico Gagliano: Oh, so they kind of make sure that they’re not psychotic.

Rachel Bloom: Make sure they’re not psychotic.

Brendan Francis Newnam: Subcontract the googling.

Rachel Bloom: Subcontract the googling. Because you want to be safe. And, really, also, get a friend who knows you well, so it’s like, “Hey, you’re really into ‘Harry Potter,’ and the person’s just like, ‘I hate people into Harry Potter.'”

Rico Gagliano: “Alan Rickman? I hate that guy.”

Rachel Bloom: Yeah, “I hate Alan…” which is like, no one should date that person. But that’s something to point out.

Rico Gagliano: There you go, James. Get someone else to do your dirty work.

Should pro-trivia players be barred from bar trivia tournaments?

Rico Gagliano: Here is something from J.R. in Chicago — completely different topic: “Should a 15-time Jeopardy champion be allowed to play at a friendly bar trivia tournament? That seems like a breach of pub trivia etiquette, no?”

Rachel Bloom: Yeah, I agree. I would say he would be… you’d have to create your own separate little contest for him, where it’s like, “OK, so you… whoever like… if you get more points than this guy…” no?

Brendan Francis Newnam: What?

Rico Gagliano: Yeah, no, I like that.

Brendan Francis Newnam: No, it’s like, how is someone… so you become so good at something, you’re not allowed to do it again? That’s ridiculous.

Rachel Bloom: Well, it depends what the prize is. If it’s a monetary prize, that’s not fair. If the prize is, like, a gag penis hat or whatever… it depends what the prize is.

Rico Gagliano: But, I mean, if you’re playing a friendly flag football game, maybe the pro football player doesn’t get to play that.

Brendan Francis Newnam: And what does he do? He gets snow cones for everybody?

Rico Gagliano: He gets to eat barbecue.

Brendan Francis Newnam: No, that’s ridiculous!

Rachel Bloom: He could play, as long as everyone knows it. I just think going and keeping it silent, and then winning and taking your $5,000 — this is very good pub trivia.

Brendan Francis Newnam: Yeah, maybe a shirt or something to identify them.

Rachel Bloom: Yeah, if you’re upfront about it. It just depends on what the prize is.

Exes, weddings and new partners

Rico Gagliano: OK. Here’s something from C in Claremont, California. This is a dire situation.

Brendan Francis Newnam: All these people are only using initials, which makes me a little nervous.

Rachel Bloom: Yeah. I like to imagine that these are all movie stars.

Rico Gagliano: So, C, that would be…?

Rachel Bloom: Charlton Heston.

Rico Gagliano: Charlton Heston in Claremont, California writes: “Some of my longtime friends are getting married this spring. There’s an excellent chance both me and my ex will be invited. I have a very casual email relationship with my ex, but haven’t told him I have a new beau. Do I need to tell him before we both arrive at the wedding that I won’t be traveling solo?” Does she need to tell her ex?

Rachel Bloom: Yeah, I’d mention it.

Rico Gagliano: Really?

Rachel Bloom: Yeah.

Rico Gagliano: Why?

Brendan Francis Newnam: You have to!

Rachel Bloom: You have a casual email relationship, and you’re going to run into him, and you’re going to bring a date to the wedding? Just be like, “Hey, yo! Just, not to be weird, just because I’m going to see you at this wedding, I just want to let you know I’m bringing my new dude. Just didn’t want it to be weird when you met him.” It’s just a casual thing.

Brendan Francis Newnam: Well, because the thing that concerns me is that if C’s asking this, C might still have some residual feelings and is maybe being an emotional vampire when it comes to C’s ex. And so, you need to own it upfront: “I am bringing someone. They will be there, and I love them, not you!”

Rachel Bloom: With all this stuff, I think, if you just do it casually, where it’s like, you title the email, subject line: “Heads up.” And it’s like, “Hey! Super psyched to, like…”

Brendan Francis Newnam: “Heads up”? That’s not casual.

Rachel Bloom: “Heads up!”

Rico Gagliano: That’s pretty casual.

Brendan Francis Newnam: No, how about, like, “Hey, wedding,” or “Wedding”?

Rachel Bloom: OK, maybe what I would do is, honestly, title it “Wedding Fun.” And then just be like, “Yeah, I’m so psyched to see you at these weddings. Just wanted to give you the heads up, I am bringing a date. Just didn’t want it to be weird when you met him. He’s a super nice guy.”

Brendan Francis Newnam: “He’s way better in bed than you, and I think he’s the one.”

Rachel Bloom: “He’s just, like, so much better.” It’s always good, also, in case this guy was looking to hook up. Because you don’t want him getting…you don’t want a “500 Days of Summer”-type situation.

Rico Gagliano: Yeah, I think you go with “Wedding Fun,” see?

Rachel Bloom: Just “Wedding Fun.”

Brendan Francis Newnam: “Wedding Fun.”

The best way to initiate a public sing-a-long

Rico Gagliano: And here’s one last question. This is from Ben in Los Angeles: “What is the best way to get people to burst into song?”

Rachel Bloom: To start singing a song everyone knows. If you’re just like, “What’s that song, ‘Sweet Caroline’?”

[Brendan, Rico, and Rachel begin singing the song together]

Rico Gagliano: Look, I’m going to do harmony.

[Brendan and Rachel sing while Rico harmonizes]

Brendan Francis Newnam: One of the only songs where you do horn parts when you’re singing, you know? Usually, you don’t do the instrumentation.

Rachel Bloom: It’s a great.

Brendan Francis Newnam: God bless you, Neil Diamond.

Rachel Bloom: That’s how you do it.

Brendan Francis Newnam: Thank you for this, subject line: “Etiquette Fun.”

Rachel Bloom: “Etiquette Fun.”

Brendan Francis Newnam: “Etiquette Fun.”

Rachel Bloom: Thank you so much for having me.