He Said, She Said: "I Wish You Would Dress Like Whoopi Goldberg" Edition

Eliot and Jackie have strong opinions about whether or not friends do pantsuits to friends.
Publish date:
November 21, 2011
best friends, fashion, friendship, outfits, whoopi, shapeups

Note: XOJane writers Eliot and Jackie are IRL best friends. This doesn't mean that they always get along. In fact, sometimes they fight like best friends do, like two pigeons over an errant curly fry. Today, they tackle the topic of whether Eliot should be allowed to treat poor Jackie like an American Girl doll. Jackie, for her part, does not want to be dressed "like Murphy Brown." Please read both of their (VERY COMPELLING) arguments, and weigh in accordingly.


I love my best friend, Jackie. She is everything you could want in a best friend: She is caring, concerned, fair, level-headed and always available with support. Since high school, we’ve watched each other navigate our twenties in different ways: me in our native New York, working my ass off to make a living as a comedian and a writer, and Jackie in the south, where she’s consistently worked in the non-profit sector because, well, basically she’s the better person (she was "super-psyched" recently when she got a part-time gig working with CONVICTS).One thing we’ve always dealt with together is our respective poor body images. We have both reformed ourselves from whence we came (she, once a “hardcore” scenester with an unfortunate razor-cut bob, and I a chubby clown, during a far, far too long period of time when I challenged myself to look like a children’s entertainer who was also homeless and crazy).But now, we’re both more or less comfortable with how we each look. In fact, we’re those guys who scroll through the Facebook pages of people from high school and marvel at, rankly, how much better we look now than we did then. Granted, it’s not that much of a stretch since we went to high school in the same area of Long Island from which Snooki lookalikes hail, and orange skin and cheap extensions don’t age particularly well (#guidetteproblems) (also, #dragqueenproblems).In fact, we both feel better than we ever have, and that’s great! And yet, there’s still an element to our friendship that I cannot deny: I am the gay guy who wants to dress up his gal pal.Problem is, Jackie does not want to be "styled." Possibly because my life’s purpose is to dress Jackie in one way and one way only: INSANELY.I don’t know what it is. I love Jackie. I think she’s very attractive. And I really don’t give a shit about fashion (aside from my obsession with Forever 21). But for roughly a decade now, I’ve been goading my best friend to wear a purple tuxedo. A purple, boxy, men’s tuxedo. Like the kind you might see on Steve Harvey or ...well, basically, only Steve Harvey.

Jackie refuses to do it. Not for my birthday. Not for the time I published a book. Not even for the time I got Bea Arthur’s face tattooed on my arm! Even then, Jackie (who was not only the first one of us to get a tattoo, but who taunted me forever with claims that Bea Arthur was already dead) flat-out refused to dress up like a closeted female stand-up comedian circa 1986.I guess part of the desire is knowing that it will never pan out. The fact is, she always -- ALWAYS -- says no to an array of daring looks.

Here are some of the ways I’ve requested Jackie dress:

  • Like a colonial woman
  • In baggy stonewashed jeans, preferably in overalls, one clip hanging loose
  • In white sneakers and a polyblend, knee-length navy skirt, "Working Girl"-style
  • In a ribbed turtleneck. Any color! (Although beige is ideal)
  • Like Weird Al, even if just on Halloween
  • Like one of the ladies from the Yearning For Zion Ranch (specifically with a 14” braided pony tail)
  • In bell bottoms, but -- and this is important -- not the flattering kind
  • In Retro Gwen Stefani’s butterfly clips
  • Platform flip flops (a Long Island staple)
  • Like Amy Grant in the “Baby Baby” video
  • Like the lady from that game show who said “You ARE The Weakest Link, goodbye!”
  • Like Murphy Brown (pantsuit preferred, but I could live with just the haircut)
  • Like Rosie O’Donnell in "Riding The Bus With My Sister" (Chucks, orange, knee-length jersey shorts, an irony-free kitten tee shirt, and a bad perm)
  • In an XXXL Big Dog tee shirt, specifically the one with the Saint Bernard wearing sunglasses and saying, “Do I LOOK like I skip a meal?”
  • Shape-Ups. Just. Shape-Ups.

I know it’s never going to happen, and I know that my requests will only be met with her reminding me of when, in an attempt to look “like Mr. Sheffield from The Nanny,” I accidentally dyed a huge chunk of my hair pee-blond, and I looked like a white trash skunk. Or that time I thought I’d go “DIY” and dye my jeans with FLOURESCENT SPRAY PAINT. Or when, right after coming out of the closet, I somehow thought it would be appropriate to wear H&M’s extremely tight, extremely floral-printed tank tops, despite the fact that I looked like Nancy Grace would on "Dancing With The Stars" if she wore glasses and a “retro librarian” wig.My only hope is YOU! If you rally for it in the comments, maybe Jackie will finally understand how much she needs to wear a purple tuxedo. Let’s make it happen! It’s the Internet! Anything’s possible!(Also, it’s not going to happen.)


I love Eliot, too. In fact, before I knew he was gay, back in 11th grade, I loved him to the point of mortifying journal entries about how much he “gets me” and how I longed to touch his face, or something.

He and Alice, our third best friend who will never read this article because she is a Luddite gnome (two months after Michael Jackson died, she still didn’t know) were the first people I didn’t have to explain myself to. I realize now that they validated me during a crucial time where I needed it, and in doing so, enabled me to be confident about the strange sort of alien that I am today.

Eliot is the best friend a girl could ask for, and I would absolutely throw myself in front of a train to save him, if that were necessary for some bizarrely specific reason. I would do anything for him, but, in the immortal words of Meatloaf, "I won’t do that.” That being, wearing a tuxedo for him.

He is my best friend, but he does not get to dress me.

He doesn’t know this, but the first time Eliot asked me to wear a tuxedo for his birthday, I considered it. I looked up how much it would cost to be fitted for one, rent it for the night. What can I say, I love my best friend.

However, as our friendship matured and I began a career in mental health, I started to realize that what Eliot was asking for was not about me: by trying to get me to dress like a 1980’s butch, he was projecting. Eliot wants me to dress in the middle aged woman outfits he won't wear himself. That sounds hard to believe, but I have prepared a list of bullets which I think illustrate my point quite nicely: - A fresh-faced college graduate, Eliot immediately moved to Park Slope. Right out of college and into the heart of same-sex-baby-carriage-pushers. His ultimate goal is to buy a “cottage.” Whatever that means. - Before he had his own dog, he would frequent animal shelters to walk their dogs around the neighborhood. Pretty much one step away from pushing a baby carriage with a sack of flour wrapped in a blanket. - His “dream car” is an Outback station wagon. - His cabinets are filled with Luna bars. - He owns a LOT of linen clothing, and defends it by talking about how it "breathes." - His style idol is Whoopi. Not in an ironic way. - For running on 5 years now, Eliot has had a Halloween theme of dressing like various middle aged female celebrities. He uses the same misshapen wig every year, which he keeps balled up in a grocery bag in the back of his closet. - Once, in an attempt to get me to massage his hand in a movie theatre (which I started refusing to do in public because he would moan too loudly) he actually said this exact phrase: “The power of human touch is incredible.” - Obsession with the "Golden Girls." OK, it was a great show. But let's talk about Eliot's deep reverence for "how strong a woman" Bea Arthur is, how she forged the way for “women of age” (his words) to be openly sexual, strong beings. Years ago I found out that Bea Arthur and I shared a birthday, and I successfully hid it from him until last year. I honestly thought he was going to have a heart attack when he found out.Just like in his Freshman year of college, newly out, Eliot is searching to find his identity. Only this time he’s doing it through me, and I’m not cool with that. Friends do not have an obligation to be the other's Whoopi paper doll.

That first year, Eliot wore some regrettable tank tops, did “promotion” for a club called “Pop Rocks” and dipped his toe into different identity pools, trying to find one that fit. Sometimes we learn to be who we naturally are by trying on different metaphorical pantsuits and seeing how they feel. The shoulder pads that he loves aren’t flattering on me, even if Murphy Brown wore them.

El, we’ll laugh about this some day, too. If you like the feeling of being a woman, embrace that. (But maybe do some research, considering your deficit of knowledge when it comes to the female anatomy. Remember the time I had to tell you that when a woman gets her period, it doesn’t “happen all at once, in a big gush” like you thought?)

If you promise to stop trying to dress me, I promise to be there when you are ready to admit that the trip to Talbots is really for you. I’ll be there to help you load your rescue dogs into the back of your Outback on the way to your summer share in Vermont....And I’ll wear a tuxedo at your wedding.