Why Would You Get DATING Advice From Jeffrey Epstein?!

Summary

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Podcast Summary: Bulwark Takes

Episode: Why Would You Get DATING Advice From Jeffrey Epstein?!
Date: November 18, 2025
Hosts: JVL & Sam Stein

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Episode Overview

This Bulwark Takes episode unpacks the shocking revelation that former Treasury Secretary Larry Summers maintained a years-long correspondence with Jeffrey Epstein—including seeking romantic advice—long after Epstein’s criminal behavior was widely known. JVL and Sam Stein delve into what these communications reveal about Summers’ judgment, the vulnerability of powerful men, and the ripple effects for institutions still connected to Summers.

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Key Discussion Points & Insights

1. Summers’ Correspondence with Epstein

• Years of Emails: Larry Summers communicated with Jeffrey Epstein before and long after Epstein’s initial conviction for sex crimes, including up to 12 hours before Epstein’s final arrest in 2019.
  • “Larry Summers is emailing back and forth with Jeffrey Epstein long before he is convicted of sex crimes, long after he is convicted of sex crimes and up to like 12 hours before he's arrested for the final time.” — Sam Stein [02:04]
• Subject Matter: The conversations weren’t just about economics. Summers explicitly sought Epstein’s advice about pursuing a romantic relationship with a woman he once mentored.
  • “Larry Summers is coming to him for romantic advice. Asking somebody who's been convicted of sex crimes for advice about women. Wow.” — Sam Stein [02:33]
• Moral Failing: The hosts note that the most damning aspect isn’t just the inappropriate pursuit but Summers’ reliance on Epstein, fully aware of his criminal history.
  • “Again, this is not pre discovery Jeffrey Epstein. This is. We know this dude's bad and I'm still gonna associate with the guy.” — JVL [02:42]

2. Summers’ Legacy and Institutional Fallout

• Troubled Reputation: Summers’ intellectual credentials are recognized, but personal and leadership flaws have long dogged his career.
  • “He was a phenomenally successful Secretary of the treasury during the Clinton boom years... Not a great president of Harvard because he wasn't really good at doing leadership and dealing with other people. Because he's not a likable person.” — Sam Stein [04:29]
• Longstanding Issues: Democratic circles have increasingly sidelined him, with figures like Elizabeth Warren actively pushing him out.
  • “There was a whole host of people in Democratic circles who were like, absolutely not. They had no willingness to even entertain the idea [of Summers for Fed chair].” — JVL [05:38]
• Institutional Questions: The revelation places pressure on Harvard, think tanks, and others to decide if continued association with Summers is tenable.
  • “All these institutions are going to face really difficult questions about whether you continue to have this association with someone.” — JVL [06:33]

3. Details of the Summers-Epstein Exchanges

• Seeking Advice about a Protegee: The woman at the center of the communications is identified in the press as a Chinese economist, currently at the LSE. It’s unclear if any romantic relationship occurred.
  • “What isn't clear to me... is whether they had a romantic relationship and then she drifted away or whether he was trying to start one. He's worried that she's only using him for his connections. And so it is like he's writing into Dan Savage, looking for relationship advice.” — Sam Stein [06:42]
• Codename ‘Peril’: Summers and Epstein refer to the woman as “Peril,” consistent with Epstein’s habit of using code names.
  • “They used a codename for this woman. They referred to her as Peril…” — Sam Stein [08:49]
• Epstein’s Cringe Advice: Epstein offers pickup-artist style guidance, advising Summers to “play the long game” and keep her in a “forced holding pattern.”
  • “Epstein urged him to play the, quote, long game and keep her in what he called a forced holding pattern.” — Sam Stein [11:23]
• Summers’ Insecure Behavior: The hosts portray Summers as emotionally immature and dangerously unaware of boundaries.
  • “You are such a failure as a human being that you don't know how to have conversations with women or relationships. And you wind up in a place where you go for advice about romance to a sex criminal.” — Sam Stein [09:26]

4. Broader Reflections: Men in Power & Arrested Development

• Insecurity Among Elites: The episode underscores how deep-seated insecurity can persist even among the most powerful.
  • “It's remarkable the degree to which the men who have reached the most power... still in their hearts are like kind of pubescent boys... deeply insecure around women.” — JVL [09:58]
  • “Men will do anything to avoid going to therapy.” — Sam Stein [14:46]
• Disqualifying Lack of Judgment: While not strictly “cancelable,” these revelations are clear evidence of Summers’ catastrophically poor judgment, particularly on issues involving women.
  • “What you have is a guy whose judgment is so bad you can't even believe it and who's an asshole. And so if you're the kind of shop that has a no assholes policy... aren't you within your rights just to say, you know what? Get lost.” — Sam Stein [12:01]
  • “I just find it icky. I find it troubling. I don't think he should necessarily be working on anything related to, you know, women's issues or women in the economy or anything like that, because his judgment on this stuff is very suspect.” — JVL [14:29]

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Notable Quotes & Memorable Moments

• On Summers’ behavior:
  “Imagine having to share, like, a faculty lunchroom with this guy.” — Sam Stein [13:40]

• On men’s reluctance to seek therapy:
  “Men will do anything to avoid going to therapy.” — Sam Stein [14:46]
  “Clearly. And even text with Jeffrey Epstein.” — JVL [14:50]

• On institutional responsibility:
  “Every employer has the right to make assessments about the people they employ. And they don't have to fire them, but they don't have to continue working with them forever.” — JVL [14:21]

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Key Timestamps

• 01:51 — Opening context on Summers’ ongoing communications with Epstein
• 02:33 — Summers seeks romantic advice from Epstein
• 04:29 — Discussion of Summers’ rocky legacy
• 06:42 — Details of the specific exchanges about “Peril”
• 08:49 — Use of codenames and Epstein’s pickup-artist advice
• 09:58 — Insecurity of powerful men
• 12:01 — Should Summers be "canceled"? Discussion of institutional policies
• 14:46 — Quips about therapy and male behavior

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Conclusion

This episode uses the Summers-Epstein email trove as both a case study in personal and institutional failure and a broader meditation on the arrested emotional development of elite men. The hosts don’t mince words about the awfulness of Summers’ judgment or the uncomfortable aftermath for organizations still tied to him. Their tone is incredulous, sardonic, and focused on the bigger implications for power, privilege, and accountability.

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Transcript

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[JVL]

Hey everybody, you're about to watch a video on Larry Summers, the former treasury secretary who's caught up in the Epstein file scandal because he basically was corresponding with the guy for a lot of time, even after the first trouble. Before you watch us, I just want you to know we recorded this earlier in the day, JVL and I to talk about whether institution should, you know, sever ties with the guy. And it turns out by the time that this thing was about to publish, Larry Summerson put out a statement saying he was going to step back from public life. Here's what it read. It says, I'm deeply ashamed of my actions and recognize the pain they have caused. I take full responsibility for my misguided decision to continue communicating with Mr. Epstein while continuing to fulfill my teaching obligations. I will be stepping back from public commitments as one part of my broader effort to rebuild trust and repair relationships with the people closest to me. Larry Summers stepping back from public life. What you're about to watch is a conversation I had with JVL prior to that statement in which we talk about why the hell he was communicating with Jeffrey Epstein many, many years after Epstein first got in trouble. Hope you enjoy.

[Sam Stein]

Hey everyone, I'm jvl here with the bulwark Sam Stein and nobody is taking it on the chin harder in the wake of the Epstein emails than Larry Summers.

[JVL]

I think Donald Trump. Donald Trump.

[Sam Stein]

But Trump isn't actually emailing back and forth. The emails are all about Trump. And Larry Summers is emailing back and forth with Jeffrey Epstein long before he is convicted of sex crimes, long after he is convicted of sex crimes and up to like 12 hours before he's arrested for the final time.

[JVL]

That was the best.

[Sam Stein]

12 hours before he's arrested for the final time. And they're not just talking about economics.

[JVL]

No.

[Sam Stein]

Larry Summers is coming to him for romantic advice. Asking somebody who's been convicted of sex crimes for advice about women. Wow.

[JVL]

It's not just that he's asking. He's trying to like pick up his mentee. There's like something really inappropriate about the pursuit itself. And then he turns to Jeffrey Epstein for advice. Again, this is not pre discovery Jeffrey Epstein. This is. We know this dude's bad and I'm still gonna associate with the guy.

[Sam Stein]

He's married the whole time. I mean, I think maybe worth saying it, maybe it's not even worth. Maybe the fact that he's married doesn't even like register once you're going to Jeffrey Epstein for romantic advice.

[JVL]

It registers. So a couple things here. One is just to dispense of the Trump. Trump stuff because I think it's irrelevant to this, but I do think it's kind of funny to note no one actually has noticed, but Donald Trump is saved to a large degree here by the fact that he religiously does not use email. He hasn't used it in. Oh yeah, he apparently had not used it for a decade starting in the aughts and doesn't text. So there may have, may not have been correspondence with essay, but they're not.

[Sam Stein]

Digital that you never take notes on. A criminal fucking conspiracy.

[JVL]

A Clear Wire fan. So let's put Trump aside. Larry. Larry Summers. I think, look, the man has a very. How would you describe his legacy at this point in time? It's rocky, almost.

[Sam Stein]

Giuliani ish. I would say almost.

[JVL]

He doesn't have like the. Yeah, he wasn't caught by like Borat and doesn't have the hair dye stuff, but he's got issues. He obviously famously had issues. Issues talking about female academics while at Harvard. People in Democratic circles find him both brilliant and incredibly insufferably arrogant. And his policy and politics is pretty outdated in Democratic circles at this point in time. But this is bringing it to a very personalized level that makes him, or at least threatens to make him incredibly, irredeemably toxic and probably will.

[Sam Stein]

I think this is such a good question because, I mean, the, the reality is Larry Summers was a phenomenally successful Secretary of the treasury during the Clinton boom years. Very, very widely respected economist and not a great president of Harvard because he wasn't really good at being like, doing leadership and dealing with Other people. Because he's not a likable person.

[JVL]

Yeah, he's not a likable guy.

[Sam Stein]

But again, very, very smart, very good economist. Not a lot of people who, who don't have access to grind, who are not willing to say, yeah, no, he's a serious economist. We, you know, we listen to the stuff Larry writes and the more you see of him outside of like economic analysis, the more he looks like a fool.

[JVL]

Yeah.

[Sam Stein]

Is that fair to say?

[JVL]

Well, 100%. Well, first of all, I quibble a tiny bit with the economist stuff. I mean, obviously brilliant man, but like his record on deregulation has, towards the end of the Clinton years had really rankled a lot of folks who think he went way too far. That's on the liberal side of the agenda. As opposed. Now to your point about looking like a fool in the non political economic realm. Yeah, I mean, 100%. Again, the arrogance, this stuff. He does not have a lot of friends in these circles precisely because he thinks he's the smartest man in the room. And he might be, but like, it doesn't really ingratiate yourself. So people forget, like during the Obama years he was, there was constantly this buzz about whether Larry was going to come back into the fold and there's a question about whether he's going to be made Fed chairman and all this stuff. And there was a whole host of people in Democratic circles who were like, absolutely not. They had no willingness to even entertain the idea. Among them was Elizabeth Warren, who did not want him involved. And they've been sort of pushing him to the periphery of these discussions forever. But he doesn't go away. He comments, he's on the Sunday shows, he does this stuff. He still has a relationship with Harvard and so he's tied to like the, you know, he's tied to cap, which is the Democratic think tank, which means that now that it's been revealed this type of proximity he had with Jeffrey Epstein, all these institutions are going to face really difficult questions about whether you continue to have this association with someone.

[Sam Stein]

Yeah, I think it's important we should actually go through what's going on here. So he and Jeffrey are going back and forth over the course of years, in this case specifically about a woman that he refers to as somebody he had once mentored. So the best reporting we have on this is from Harvard Crimson, who, who has identified the woman they believe to be it. She's a Chinese economist now at lse, I think. And what isn't clear to me from the way Summers is writing to Epstein is whether they had a romantic relationship and then she drifted away from him and he was trying to get back in or whether he was trying to start a romantic relationship and he's worried that he's being friend zoned or in this case, like connections zoned because he's worried that she's only using him for his connections. And so it is like he's writing into Dan Savage, you know, looking for relationship advice or something.

[JVL]

He like re. He like rereads the text that they sent or the messages, and he writes to Epstein. He's like, she must be very confused or maybe wants to cut me off, but wants professional connections a lot and so holds to it. And like, Epstein's giving him little tidbits of advice. She sounds needy. He writes back and he gives a little smile emoji. You know, I read it as him pickup artist bullshit.

[Sam Stein]

But like, saddest pickup artist ever.

[JVL]

He's like, hey, Jeffrey, you seem to have a lot of women around, and I'm kind of this academic nerd and I really am interested in this person who I'm a mentor for. Can you, like, give me some advice on how to score? And it's just like, I gotta be honest, like the whole thing about. And this gets to the broader issue about the Epstein stuff. Like, obviously the whole conspiracy was this is a cabal of elites who are just going weird places and in fact criminal places with young women. And I was like, could it possibly be that? And then the more you see of these emails in these texts, the more you're like, actually, yeah, it is. The most powerful people in the world all interconnected with this one guy. It's wild.

[Sam Stein]

So another important tidbit here is they used a codename for this woman. They referred to her as Peril, which, if you remember the birthday book and Donald Trump's bizarre use of the word enigma I think could be significant if referring to women by codenames is a thing that Jeffrey Epstein did with his dad.

[JVL]

It appears so, yeah.

[Sam Stein]

All of a sudden, the birthday poem makes more sense from Trump. So here Epstein jokes, quote, the probability of you in bed again with peril was zero. But then he says to Larry, she is never ever going to find another Larry Summers. Probability zero. Hey, bro. Gotcha, bro. Like it is, can you imagine being a 60 something year old man and this is your life. You are such a failure as a human being that you don't know how to have conversations with women or relationships. And you wind up in a place where you go for advice about romance to a sex criminal.

[JVL]

Well, someone said it, like, very interesting where they're like, it's remarkable the degree to which the men who have reached the most power and have accumulated the most respect from their peers still in their hearts are like kind of pubescent boys. Right? Like, just trying to figure it out. Deeply insecure around women, which probably drives a lot of their behavior, and just looking for, like, comfort or answers or anything to get through the insecurity. And Jeffrey Epstein, who clearly was a master manipulator, played off of this stuff incredibly well. Obviously entertaining, you know, Larry Summers worst fears and saying, no, no, don't worry. This is what you have to do. And it's just so weirdly psych. Like, I don't know, it's creepy, obviously, but it does give you an insight into the incredible insecurities that these people have. Even when they hit incredible power levels.

[Sam Stein]

They're all 12 years old.

[JVL]

Yeah.

[Sam Stein]

Somebody said on. On the Internet, like, right. This is the. The deep insight is they're all 12.

[JVL]

You got to get to the kicker of this story, though. It's the best part of the entire story.

[Sam Stein]

Throughout June, Summers fed. I'm just reading from the Harvard crimson.

[JVL]

This is 2019. Okay. Epstein is already very much in trouble. They're still talking. Okay, go ahead.

[Sam Stein]

Summer's fed. Epstein updates about the women's workload and continued contact. He's just like, texting. Epstein is like, you know, hey, you know, she's got a lot of work right now. That Epstein urged him to play the, quote, long game and keep her in what he called a forced holding pattern. Oh, I get it, man.

[JVL]

Yeah.

[Sam Stein]

For a force, I'm the one who's got the hand in this relationship.

[JVL]

This is pickup artist.

[Sam Stein]

It is.

[JVL]

It really is. Yeah.

[Sam Stein]

The final messages, dated July 5, 2019, show Summers still in regular contact with Epstein. That morning, Summers wrote, he was in Cape Cod with his family. Bit of an Ibsen play, he joked. And the two men exchanged a brief flurry of literary one liners. The thread ends at 1:27pm Epstein was arrested the next day.

[JVL]

Unreal. Unreal. I guess that's the end of the text relationship.

[Sam Stein]

On the question of whether or not Larry Summers should be canceled for something like this, I think this hits a real gray area, okay. Because nothing in this seems to be illegal. Nothing seems to be unethical in the. I was hitting on my grad student, right? I mean, it's unethical in all the other ways. Like, it's. Don't get Me Wrong. It's unethical, but not within, like, the strict dynamics of, like, professional relationships. Yeah. What you have is a guy whose judgment is so bad you can't even believe it and who's an asshole. And so if you're the kind of shop that has a no assholes policy, which I believe is the only kind of shop to have, aren't you within your rights just to say, you know what? Get lost. I'm sorry, we're just not doing this. We're not doing this with you. And it doesn't have to be some grand, like, oh, we're canceling your site, but is that wrong? Maybe that would make the Free Press very upset. Maybe Barry Weiss is going to wind up defending because we got to be prepared if that all happens. Larry Summers winds up at the Free Press.

[JVL]

I'm sure he's written for the Free Press already, but, yeah, good question. So, like, you don't have to cancel him for this. Although it's unclear if she was a student or a mentee, but I think it was enough that it's not like a cancelable offense, but you also don't have to employ the guy. Like, there's got to be a place in between where you're like, I'm not firing you, but also, I don't want to renew my contract with you. Right. Like, you don't. There's no obligation to employ this man. What he's providing you as a service does have to include what you think he's bringing to the table in terms of his character, his expertise, and his judgment. His judgment.

[Sam Stein]

Imagine having to share, like, a faculty lunchroom with this guy.

[JVL]

No. And, in fact, I would not want to. I would think, again, his judgment in corresponding with Jeffrey Epstein in 2017, when everyone knew about this stuff and 2019. Yeah, he should have known about this stuff if he didn't. You know, I think that's real. I think that's really problematic. And I don't think Harvard would be wrong to say, hey, I appreciate everything you've done, you know, work through the end of the year or whatever, but, like, you know, let's go our own ways. It's fine. That would maybe be interpreted as being canceled in some quarters, but every employer has the right to make assessments about the people they employ. And they don't have to fire them, but they don't have to continue working with them forever because they just happen to be employed. And so, like, again, I just find it icky. I find it troubling. I don't think he should necessarily be working on anything related to, you know, women's issues or women in the economy or anything like that, because his judgment on this stuff is very suspect.

[Sam Stein]

You know, as the Internet joke goes, men will do anything to avoid going to therapy.

[JVL]

Clearly. And even text with Jeffrey Epstein.

[Sam Stein]

Boy, howdy. Yeah, Larry, just go get a therapist. I mean, you could talk with a therapist about your romantic. A therapist who isn't even going to jail, probably. All right, Sam Steinman, good talk. Always good being with you, sort of.

[JVL]

Oh, come on, don't feed this bread.

[Sam Stein]

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[JVL]

It would be crazy if there were any catches. But there aren't, right?

[Sam Stein]

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[Sam Stein]

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