Talia Lichtstein on Hooking Up with a Married Boss: “Hot”, “Sexy”, “Salacious and Bad” but “Fun”!

On the “My Best Friend Is Hooking Up With A Married Man” episode of the Basic Training podcast (November 20, 2023), a caller left a “juicy” voice message for co-hosts Jake Cornell and Talia Lichtstein. In the message, the caller asked for advice concerning her 23-year-old best friend from high school whom was “hooking up” with her much older married boss. The caller “cut things off with her”, but she wanted to know if she were being “too harsh”. Here are the “juicy” parts of the message:

“She was 23 and started hooking up with her boss who was probably low 40s. Her boss is a married man [...] But they would, you know, eventually hook up when she was working or after work or whatever [...] I cannot respect this thing that she’s doing as a child of divorce. Um, and I basically cut things off with her just because I couldn’t keep her secret anymore.[...] But sometimes I wonder if I was being too harsh on her [...] I’m I being too harsh on her?”

In response to the message, Lichtstein opined, “Such a good call.” And Lichtstein immediately took sides, “I’m on the side of the friend that she’s dissing.” Why did Lichtstein take the side of the 23-year-old who is\was having an affair with her “low 40s” married boss? Lichtstein did so because the 23-year-old sounded “[...] fun as fuck!” So much so that, Lichtstein shared, “I would like to be her [...]”

Interestingly, Lichtstein admitted, “Of course, it’s wrong - no shit [...] She should stop. She’s doing a very bad thing. But also, that’s life and what are friends for? [...] I think that, honestly, you are being too harsh on her.”

Lichtstein stated that having an affair with a married boss is wrong; however, that didn’t stop her from seemingly insulting the concerned best friend by calling her a “prude” and a “fucking loser.” Lichtstein advised her to “[g]et a grip” and to stop “assert[ing] your moral high ground”.

“You’re a moral person. Congratulations. You have the moral high ground.”

“I think you're being a little bit of a prude [...] a fucking loser.”

“[...] don’t you want shit to laugh about when you’re old with your friend. Get a grip. Have some fun with this.”

“I think that a lot of what doing here is trying to assert your moral high ground and make yourself feel better [...]”

But why did Lichtstein condone the age-gap affair if she considered it to be “wrong”? Lichtstein related that it may be wrong, but it’s “hot”, “sexy”, “salacious and bad” but “fun”:

“[...] it’s so hot to be fucking a boss.”

“It’s, like, so sexy.”

“It’s so salacious and bad.”

“It makes any job more fun. Imagine going to work everyday and you're so annoyed that you have to go to work but at least you get off and you get to go ‘do a little flirty’.”

Previously, in the Substack, “Talia Lichstein and Sydnee Paige: NYC Influencers Who Prefer (Much) Older Men”, we wrote about Lichstein’s affairs with (much) older men. However, despite her best effort, Lichtstein confessed that she has not been able to have an affair with one of her (married) bosses. Lichtstein admitted, “I’ve tried so hard to have that, but it hasn’t happened. I have wanted that.”

As an example, Lichtstein shared that she was “obsessed” with her summer camp boss whom wasn’t even her type, but intriguingly, his position as her boss made her “obsessed” with him and the, ordinarily unattractive, man transformed into a scary-hot-boss whom took over her life. In the end, Lichtstein admitted, “I can’t blame your friend - honestly.”

“I was obsessed with one of my bosses that I worked for when I was working in a summer camp. Not because he was hot. He’s actually, like, really gross. [...] Oh my God! He wasn’t really gross. He was, just, like so not my type. [But] the fact that he was my boss. Oh, I was obsessed. [...] it actually is scary how hot that is. It takes over your life. I can’t blame your friend - honestly.”

Lichtstein’s statements are revealing, because the common sentiment (among feminists) is that an employee could never be in a consensual affair with her boss and that a boss, by his higher status, has the (magical) ability to turn an employee into a non consensual sexual zombie. Of course, there are instances where bosses have abused their power (of attraction), but it’s not uncommon for employees to welcome affairs with bosses that in some cases, to the delight of (ultra) Orthodox Jews and Muslims, has led to marriages.

For example, on CBS News, Constantine von Hoffman posted “Survey: Many employees date the boss” (February 14, 2013). Hoffman wrote that 29% of survey respondents shared that they had dated a superior and that over one-third of women were more likely to date a boss:

Perhaps more surprisingly, nearly the same number -- 29 percent -- said they had dated someone above them in the company hierarchy, with 16 percent saying they had dated their direct supervisors. This could be why just over a third of workers reported they had to keep the relationship under wraps. Women were significantly more likely to date someone further up the organization chart -- 38 percent, compared to 21 percent for men.

More recently, Emily Sundberg posted a link in Feed Me to Alexandra Molotkow’s Business Insider piece “Your secret work crush: Half of everyone you work with has an office crush” (April 8, 2024) where Molotkow profiled Karis, a married architect in her 20s, whom had a crush on Stefan, her married boss, which lasted for five years.

Subsequently, Sundberg took a(n) (anonymous) survey of her readers about their potential work crushes, and she got: "[...] hundreds of remarkably vulnerable, albeit anonymous, responses" some of which she posted on "Nothing sexy happens on Slack." For example: 

"He was a VP at the firm, I was an intern."

“We secretly dated for 4 months. It was hot but the power dynamics weren’t healthy. I was like barely 21 and he was 10 years older & my boss. It was worth it for the plot though. Pretty sure everyone knew besides his superiors.”