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Crossdressing best friend wants to go out as a couple
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Abigail Van Buren | Syndicated Columnist
 | Northwest Florida Daily News

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DEAR ABBY: My best friend and I are both male and 25. We’ve been friends since third grade. We were apart for four years of college and two years after because we were employed in different states. He has now been transferred and lives and works a few miles from where I do. We see each other frequently and often double date.
He recently shared a secret after pledging me to secrecy. He’s a cross-dresser. He says he’s not gay, and I believe him. He has pictures he had taken professionally in which he is completely feminine and even beautiful. He says he has been dressing up since the age of 12.
Abby, he wants to go out in public with me as a couple. Even though he is small and would easily pass, I’m just not into it. And what explanation would I give to my girlfriend? He says if I won’t, I’m not a true friend; I say HE isn’t. Is there any way to resolve this? — TESTED IN TAMPA
DEAR TESTED: There is a way, provided your friend is open to it. How about you and he and your girlfriend going out together? Of course, your girlfriend would have to know the truth, and your friend would have to be OK with her knowing. This way if you were seen with “another woman,” it wouldn’t cause conflict with the woman you’re dating. That said, you should not do anything you are uncomfortable with, so think carefully before deciding.
DEAR ABBY: I am in a relationship with a woman 25 years my junior. We talked at length about some of the issues we might encounter before we embarked on a relationship. We love each other completely. Her father, however, strongly disapproves based solely on our age difference. He has stated that he had no issues with me personally.
She recently told me that she isn’t happy and she wants us to spend some time apart. Neither of her two marriages worked out. She says I’m not the issue.
She wants to be with me, but her father would shun her — and me — if we were ever to be in the same room. He has actually said he’d walk out if I were present. She told me he was this way with her first marriage, which he did not approve of.
What do I do? I love her, but I can’t get her to see how much I love and care for her and her two boys. How much space should I give her to figure herself out? — TORN UP IN PENNSYLVANIA
DEAR TORN UP: The woman you love may be twice divorced, but she isn’t free. She is firmly under her father’s thumb. The age difference is the least of your worries.
Regardless of your feelings for her, because she says she is no longer happy with you, it’s time to make a U-turn. And when you do, suggest that if she wants to have a future with anyone, it will happen sooner if she starts talking with a licensed therapist about her relationship with dear old Dad. She will never have a life of her own while he’s running it.
Dear Abby is written by Abigail Van Buren, also known as Jeanne Phillips, and was founded by her mother, Pauline Phillips. Contact Dear Abby at www.DearAbby.com or P.O. Box 69440, Los Angeles, CA 90069.



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Since the inception of drama, people have always experimented by creating something unconventional on screen. Although initially the unconventionality may not have been welcomed by most audiences, they did learn to appreciate its presence over time. Theatre has always been the first medium to display such changes and stage actors, known for their diligence and eagerness to explore every opportunity, were the earliest artists to switch genders for their portrayals. The first traces of cross-gender acting can be noticed in Shakespeare’s works, especially ‘The Merchant of Venice’ and ‘As You Like It’ which feature female characters cross-dressing to progress in an oppressive society. During the same period, the extravagant Japanese Kabuki theatres introduced “onnagatas” or male actors who played women’s roles and “wakashu” or female actors who specialized in adolescent male roles, in plays that dealt with themes regarding male homosexuality.
As usual, the English-speaking industry showed reluctance, and it was only after cross-gender performances by some acclaimed actors that people started to pay attention to the role of cross-dressing in entertainment culture. Though the cross-gender roles in today’s movies are written by vagabonds, who believe lame sexual innuendos can make up for lack of creativity, we can look back at the independent features that intend on acknowledging audiences with the truth. As of now, there has been a massive change in the relevance of such roles, from existing for comical and dramatic effect till the 90s to revealing the atrocities faced by crossdressers and people on the various spots on the spectrum of gender and sexuality.
Crossdressing has always attracted attention, be it in real life or in reel. And moviemakers have experimented with this theme in films that required a man to play a woman or vice versa, ever since the idea struck them. In the olden days, when women were not given enough freedom to step out of the house (and that was prevalent everywhere in the world, not just in India!), men got into women’s costumes to play the part, and boy, they performed well too! Since then, the trend of male actors getting into gowns to play a crossdresser has only seen positive changes in movies.
Now, I understand that some choices on the list might be controversial, and I also assume that different sections may have varying opinions on them, but let me remind you, the primary criteria is the effectiveness of the performances on a critical and emotional level. So here is the list of top crossdressing movies ever. You can watch the best cross gender movies on Netflix, Hulu, or Amazon Prime.

When Sebastian leaves for London to pursue his musical dreams, his twin sister Viola takes his place in his boarding school, eventually going on to win his soccer coach’s trust during a series of tryouts and also dates (while still cross-dressed), much to her own chagrin and churning of emotions inside. Andy Fickman’s ‘She’s The Man,’ starring Amanda Bynes fared well at the box office, and audiences loved the actress’s transformation into a man, which she pulled off with great ease.
Many actors dread getting into women’s costumes for even one scene in a movie, but late actor Patrick Swayze readily agreed to portray a full-fledged role of a drag queen and surprised us all. Swayze effortlessly played crossdresser Vida, who, along with his friends, goes on a road trip to LA not just to participate in a pageant but also win the title of Miss Drag Queen America. Patrick Swayze, who was a good-looking actor, made for one eye candy in the comedy film without going overboard in the acting department.
‘Albert Nobbs’ is probably the least popular movie on this list, even though it features five-time Academy Award nominee Glenn Close in a performance that is a very apt reflection of the society and its acceptance of women in Victorian Era Ireland. Albert Nobbs dresses as a male butler in the most elegant hotel in Dublin. Nobbs doesn’t need to confront her sexual orientation, and neither has doubts about it. She doesn’t indulge in romantic affiliations and dreams of being an independent person, a life route that is deemed inappropriate for women. Though her option is out of necessity, but unlike others on the list, this necessity does suppress her desire to be able to express the person she truly is.
The word “cult following” is thrown around a lot nowadays, with most movies that are panned by critics and preferred by a section of people being lazily termed so. ‘The Rocky Horror Picture Show’ is a tribute to the sci-fi films of the 40s-50s with a huge dose of sexual innuendos and the then-contemporary rock music. It initiated a stringent cult and eventually became the first midnight movie, a tradition that has been carried on by its fans for more than 40 years now. The movie has since enjoyed an iconic status and has had a massive effect on films,TV shows, music, and the entertainment industry in general. It is a reimagination of Shelley’s ‘Frankenstein’ with Tim Curry playing Dr. Frank N. Furter, a transvestite scientist from “Transsexual, Transylvania.” He is phenomenal in reprising the role he had played since 1973 in plays of the same name. With a bigger stage to showcase his character’s absurdity Curry never feels uncomfortable in fishnet and flourishes in every frame.
Let’s set aside the countless factual inaccuracies of the movie and its failure to convey the message it is built upon, even after 2 hours of cinema. Let’s solely concentrate on Eddie Redmayne and his portrayal of Danish painter Lili Elbe, who was one of the first known recipients of sex reassignment surgery. This serves as yet another showcase for Redmayne’s constantly rising potential and earned him a second Oscar nomination in two years. With his lean and timid framework, he is very convincing as Elbe, and his conscientious body language speaks a thousand words. The only downside of this performance was the pretentious characterization that let itself succumb to melodrama and tragedy instead of trying to celebrate Elbe’s life. Elbe was a multi-dimensional person drowning in a whirlpool of confusion and self-doubt. Though Redmayne does depict the depersonalization process through his quirky eye movements, he is never really able to get under her skin, but then nobody could, not even Elbe herself.
‘Some Like It Hot’ came out when the industry was still under the constraints of a morally primitive censorship code and hence wasn’t given a license. The film was rated as the best comedy by the AFI, and its specialty lies in its ambition to be genuinely funny while inserting an insightful subtext. In one of the earliest depictions of cross-dressing on screen, the film is more than just a cheap joke played at the expense of its characters. I have considered both the actors since it would be a sin to separate their equally remarkable efforts. The cross-gender pair formula has been adapted in recent times to horrendous results, as none of them manage to capture the vital satire in this movie instead of using its two characters’ appearances to frame a plotless comedy. Curtis and Lemmon play two musicians who cross-dress in order to escape from the clutches of the mafia who find out about their presence at a crime scene. Both Curtis and Lemmon fall for the gorgeous Marilyn Monroe and get entangled in a series of screwball events that open up spaces in them they were unaware of.
Cillian Murphy. Those dreamy blue eyes and chiseled cheekbones could make any woman swoon, and with his incredible acting talent, he has cemented his place as one of the finest Irishmen to have worked in the industry. After working in ’28 Days Later’ and ‘Batman Begins,’ Murphy starred in this dark comedy as a transgender person who was abandoned as a child and is now searching for love and her mother. He studied women’s body language and mannerisms for a few weeks and also sought advice from a drag queen who instructed him and took him out clubbing with other trans people. With his already charming looks and a grizzly hairdo, Murphy is unrecognizable to the people around him as well as the audience. The movie is pretty sad, and the situations Murphy’s character finds herself in can’t be termed as shocking, we are aware of what’s to come, but its depiction on screen is quite overwhelming compared to the one created in our heads.
Cate Blanchett can rightfully be honored as the greatest actress of our generation. Taking a look at her illustrious work, she has preferred to tackle real-life roles. From playing Queen Elizabeth I to the legendary Katharine Hepburn, she has molded her talent into a wide variety of characters, but the range surprisingly does not end here. In what can be termed as a strange and daunting choice, she opted to don the grizzly hair and those iconic Ray-Bans to play Bob Dylan! ‘I’m Not There’ explores six different stages in Dylan’s life that are played by six different actors apart from Blanchett, including Christian Bale, Heath Ledger, Richard Gere, and Ben Whishaw. Her usual unrivaled presence on screen is evident here as well as a shocking resemblance to Dylan, and this may be a visual treat for his fans, who can’t help but be transported back to the ’60s.
Tilda Swinton is renowned for her androgynous chic looks, and her photo shoot with the late David Bowie proved her talent to mask her body, something that would keep you puzzled about her true identity. We aren’t interested in her personal preferences though, and her flawless talent is too captivating for us to wonder about that. In ‘Orlando,’ she plays an ageless man who’s torn apart between his sexuality and the gender imposed upon him. We see his acceptance of different aspects in his life as the world around him progresses. The film also has Quentin Crisp, a male actor who plays Queen Elizabeth I, but it is the characterization of Swinton’s Orlando that is nothing short of a miracle, courtesy of the source material by Virginia Woolf, which is considered a classic among transgender and feminist communities. Midway through the story, Orlando changes into a woman, and this is a very difficult task to accomplish, keeping in mind the flow of the movie. Swinton holds on to the two different personalities so effortlessly you never really notice the physical transformation.
An Oscar, a Golden Globe, and sweeping almost every major award out there, Jared Leto turned into a superstar after this performance. I’ve encountered people claiming ‘Dallas Buyers Club’ to be Oscar bait, but regardless the same cannot be said about its actors. Leto’s Rayon had people debating over the effect of make-up design and delicate subject matter on such roles, with some questioning the unconventional casting of a “male” actor, and though they did contribute to success, they feel like desperate arguments undermining the credit he deserves. As a person with AIDS, Leto delivered a career-best performance and remains one of those rare actors who have switched genders to “be” the character and not for inducing an over-dramatic or comical edge. Leto is known for his psychotic dedication towards his roles, and he dropped to 50 kgs to play a terminally ill person while also opting for isolation to bring out raw emotions, similar to his co-star Matthew McConaughey. His acting towards the end is a complete revelation, right from him donning the neatly tailored suit to the haunting scene where he confronts himself in the mirror.
Though there were some renowned cross-gender performances by the 80s, it was Hoffman’s portrayal of Michael Dorsey that made mainstream audiences familiar with the possibility of cross-dressing. Hoffman was the biggest star in Hollywood after winning the Oscar for ‘Kramer vs. Kramer’ and surprised the industry by taking a step that was considered too effeminate for the desired “lead man.” Dorsey is a reputed but struggling actor who decides to dress up as a woman to get a female role. Now, the biggest reason why the movie is deemed “culturally, historically, or aesthetically significant” is because, unlike the shallow and mindless comedies nowadays, it rises above sexual innuendos to make a bold statement with some sweet farcical moments. It showcases sexism, absurdity of soap operas, the agents in the industry, and the consensus’ reservations about social statuses, and since Hoffman himself opted for control of creativity, the film is spot on with these representations.
Though Hilary Swank hasn’t been very prolific lately, there was a time when she was considered to be a power-packed female performer, taking on roles many male actors would have physically and mentally succumbed to. Though being popular for her Academy Award-winning performance in Clint Eastwood’s ‘Million Dollar Baby,’ it was her portrayal of Brandon Teena in the indie biopic ‘Boys Don’t Cry’ that made her a revered name among filmmakers and critics. The film explores the relationship between Teena and his girlfriend while also depicting the disturbing sexual assault and murder. Critics called Swank’s performance “one of the greatest Best Actress Oscar-winning performances,” and I believe that its intensity hasn’t been replicated since then. Dwelling on such heartbreaking subject matter can be very tricky, with even the slightest of mistakes turning something emotional into something melodramatic, and with the help of subtle characterization, Swank delivers something so heartfelt, the viewers are shifted back to the place and time when Teena went through all those monstrous adversities.
When San Francisco voice artist and devoted father Daniel goes through a bitter divorce with his wife, he loses his children’s joint custody. That was when our hearts reached out to the character, brought to life by funny man Robin Williams. But when he stepped back into the house cross-dressed as an elderly Scottish nanny Mrs. Euphegenia Doubtfire
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