Grinding the Mirror
In Chinese slang, “grinding the mirror” is a description of tribadism. A more tasteful and universal euphemism for lesbian sex should be embracing the mirror. The photo of Chelsea Handler in her closet is perfectly symbolic. In the November/December 2017 issue of Playboy, the actress/comedian said: “I don't know if I would be with a woman when I was sober. It was more of, you know, being really drunk, and we were with a guy. But yes, I've been with a girl. More than once, when I was younger. I haven't done that in a long time.”
In June 2023, she told Andy Cohen on his SiruisXM radio show about a threesome that she had with Ted Harbert and their masseuse. To give you a frame of reference, time-wise, Chelsea had split up with Ted in 2010, and he married another woman in 2011. Back to her interview with Andy, Chelsea said: “I’ve slept with a woman but I haven't dated a woman. I was very turned on by this woman. I ended up hooking up with her several times without the guy that I was dating. That's when I knew it was time to break up with the guy.”
That’s an awful lot of inebriated sex. Perhaps alcohol is her liquid courage rather than an accidental side-effect. For the record, Chelsea Handler quit drinking in 2014. For a bisexual woman, she’s more female-leaning since she’s more into FFM than MMF: “It’s fun, I mean, I don’t want to get double-teamed by a guy but I like a girl in the situation. She can do all the stuff that I’m too f#*king lazy to do. If a guy wants to have penetration with another guy, I'd question that. Maybe oral is less questionable…I don’t know, I’ve never been up against this kind of conundrum.”
Chelsea even played a lesbian on Will & Grace. On her Twitter feed, she has made references to lesbians and lesbianism in general. When she had her own chat show from 2007 to 2014, Chelsea Lately, she interviewed many women who were either closeted or out. Back to that Playboy interview in 2017, earlier that year was when it became apparent that Chelsea may have experienced infatuation and more with Elisabeth Moss. Chelsea was liking all of her Instagram posts as well as commenting on them.
On her show, Chelsea grabbed the posteriors of her female guests and talked about their bodies. She even did a nude sketch piece with Sandra Bullock, albeit pixellated nudity. Not even a similar piece with Conan O’Brien did much to straighten out her image. To be fair, there was one interview where lesbian actress Taylor Schilling had spanked Chelsea. Her guests were more candid than she is. Eva Mendes admitted to threesomes with women whereas Chris Colfer and Vanessa Carlton first came out on their show. The young Hollywood women who she interviewed had crushes on her. Her round table usually had at least one gay comic every show and they were always talking about gay topics.
For a person who shamelessly flaunts herself and others, Chelsea Handler is actually quite subtle. In a 2013 interview with Andy Cohen on his Watch What Happens Live show, she carefully implied that Taylor Swift is a lesbian whose boyfriends are beards: “My theory about Taylor Swift is that she's a virgin, that everyone breaks up with her because they date her for two weeks and she's like, "I'm not gonna do it." And they're like, "Oh, well, forget it. Then I don't want to date you." Every guy thinks they're going to de-virginise her, and they're not. She's never going to get de-virginised, ever, ever, ever, ever. I mean, she's just dated so many men.”
Strangely, Taylor’s interviews on Chelsea Lately are not available to watch online. In 2014, Chelsea’s roommate was a big shot attorney at Thompson & Knight who was originally from Dallas. She was 50 but looked younger. Not only that, but the roomie was single. Chelsea’s other roomie was a lesbian colleague from Chelsea Lately. About Chelsea herself, somebody on her show asked her if she was gay and she said that she is sometimes. She stuttered when Howard Stern asked her about sapphic sex. You should witness Chelsea’s response to Barbara Walters asking her about her sexual orientation.
I can imagine many readers felt ripped off years after purchasing her 2005 sex memoir, My Horizontal Life. The only anecdote about a threesome is finding out that her English boyfriend Peter had two-timed on her by hooking up with two Oriental women. Ironically, he had previously failed to get Chelsea to have a threesome. I guess the revisionist excuse would be that she was too wasted to remember, unless the threeway anecdotes after the fact were an alibi to avoid being accused of homophobia. Elsewhere in the book, she mentioned that she lied to her father about her sexuality because his best friend in high school had married a woman who left him for another woman. Even when Chelsea was a child, her older sister Sloane made her speechless during an argument by saying: “If anyone’s a lesbian, it’s you.”
There’s also the issue of Chelsea’s relationship with drugs. The book never gives you the impression that she’s into cannabis other than a cursory level at best i.e. she recalls having tried laced marijuana and, on another occasion, being too drunk to smoke marijuana that wasn’t laced. If she was having a lot of drunk sex then she would have been also having a lot of stoned sex. It’s better to have sex in a high state than in a state where you could vomit. You’re also less likely to puke if you take cocaine before sex. The truth could be that she wouldn’t admit in interviews to having sex under the influence of drugs because then she would have been monitored by police or even blacklisted by media corporations.
As for her book, she did say that she has a rule to never experiment with drugs under scorching heat with the exception of alcohol. She also admitted that she, at the age of 25, became a regular user of ecstacy in order to fit in with a dance club. From when the book was published in 2005 to when she was interviewed for a Canadian cannabis magazine (Kind) in late 2023, Chelsea and society in general have a come a long way, so she can afford to be more liberal about her drug use if not the full extent of her sex life. She takes THC edibles every day but she never lets the use interfere with her work. She doesn’t consider herself to be a pothead or stoner. Having said that, she is quoted in the Spring 2014 issue of Paper as having said: “Write drunk, edit sober.”
It’s a shame that she never became a film star or a TV star in the 20th century, but this also begs the question as to whether she was perceived as being too tomboyish to make it as an actress. She looked like the soft butch version of supermodel Claudia Schiffer. For many actresses in the last century, sexual orientation was often the difference between make and break. A married actress or an actress in a heterosexual relationship was more likely to be cast than a lesbian. Besides the influence of the conservative market (especially down South of the U.S.), there was the issue of some actresses being cast because the director or producer thought that he stood a chance of hooking up with them. You don’t hear stories of casting directors sleeping with actresses.
In 2010, when she first interviewed Taylor Swift, Chelsea Handler had a lot to live up to. The below advert from the March 2010 issue of Marie Claire sums up where Chelsea was in terms of mainstream media hype, right down to the feminization of her image. The way that it works with closeted female celebrities is that you need to primarily appeal to straight men and straight women since they are the majority, but Chelsea still left in those queer comments so as to cater to the WLW demographic whether it be lesbians or bisexuals. She may have been reserved but she wasn’t against being the host for the 20th Annual GLAAD Media Awards in May 2009. The Gay & Lesbian Alliance Against Defamation don’t just let any famous person host their ceremony.
Her credibility was immortalized when she was interviewed for an April 2008 issue of a magazine aimed at gay men - HX (i.e. Homo Xtra). The magazine had been around since 1991, and the site had been around since 1995. Anyway, Chelsea was asked by reporter Brandon Voss about her previous show (The Chelsea Handler Show) where she was looking for a gay best friend. When asked what qualities that she looks for in a gay friend, Chelsea said: “I think I like bottoms. We have a top working for us now and he's so massive and big, and I just have this image in my head that that's what all tops are like. He scares the sh!t out of me. I have a ton of gay friends. What's not to love about gay guys? They're the best. I don't like catty gay guys – gay guys who are like, “She did this and that!” – and act like women.”
She was also interviewed for the July 2006 and 2008 issues of another gay guy magazine called Instinct. Now as far as men go, if Chelsea was truly bisexual and so gay-friendly, she would have teamed up with two bisexual men for threesomes where the emphasis is on her tag-teaming with a man by her side instead of having two straight guys work their magic on her. Ironically, for all of her talk on being a gay ally, she is really all the more for female companionship. Her Instagram posts speak for themselves. I’ve never seen a female comedian embrace nudity and sexuality in quite the way that she has. Not even Whitney Cumming comes close. For a 49-year-old woman who supposedly loves men, Chelsea has never been married, let alone have children. She’s not exactly a milquetoast conservative who’s vanilla in the bedroom. Chelsea Handler’s middle name is Joy, which lends itself all to conveniently for a joke that references a popular 1972 book called The Joy of Sex.
Despite hosting the 2009 GLAAD Awards, Chelsea was disappointed that they failed to include Chelsea Lately in their 2009 report on the depiction of gay, lesbian, bisexual, and transgender people on television. In 2011, she spoke to NBC News about being an LGBT advocate when asked what charity that she contributes to the most: “I probably do the most for the gay and lesbian community, or LGBT, but I don’t have one that I focus on. I just try and kind of do a lot for different charities. GLAAD - I like to get involved with because I think it’s important to be involved with charities that don’t necessarily reflect what you’re dealing with in your life. So, for the gay and lesbian community, even though I’m not gay I think it’s really important to speak out for people that aren’t necessarily dealing with the same circumstances you’re dealing with and don’t have the benefit of the health care system or the government that you do.”
Like Eddie Murphy who joked so much about transvestites before being caught picking up a transsexual prostitute, Chelsea jokes too much about lesbianism to be considered a homophobic heterosexual or a self-conscious bisexual. Not even fellow comedian Ellen DeGeneres had the word lesbian on the tip of her tongue on her own chat show to much the same candour. Then again, Ellen was self-conscious after the final season of her sitcom - years before she became a chat show host. Given the issue of strict confidence, one wonders what Chelsea tells her therapist. To conclude, here is a quote from the stand-up star on her show: “I am not a full-time homosexual, but I do party like one.”