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  I sat there thinking, Wow. This dude had been married and ipso facto been having sex with a guy—gross. It was something I could never imagine doing because to me, even though I was anatomically a woman, inside I was a man. Wanting to have sex with another man would mean I was gay. I was definitely not gay.

  As it turns out, Brian was. He was going to go through the entire transition process—including surgery—to become a man, only to still be attracted to other men. When he told us all this, my first thought was, Why bother? Just live your life as a woman, date all the guys you want, and society will deem you “normal.”

  And that’s when, as Oprah would say, I had my “aha moment.” Brian’s gender identity was completely separate from his sexual orientation. Like me, his gender identity was male, but while I was “straight” (attracted to women), he was “gay” (attracted to men). He still looked in the mirror and hated what he saw just like I did. The fact that he was still attracted to men had nothing to do with that.

  Bottom line is, your gender identity has no bearing on whether you are gay or straight. Think of it this way: Sexual orientation is who you go to bed with; gender identity is who you go to bed as. That distinction is what really made it click for me.

  But understanding it didn’t make everything all better. I was still extremely depressed and crippled by the fear of what my future had in store for me. I couldn’t focus on anything else.

  When I relayed these symptoms to Bet, she suggested I consider an antidepressant and mentioned the relatively new drug, Prozac. I was adamantly opposed to the idea for a number of reasons. At the time, there was a stigma attached to the medication—to many people, taking it meant you were mentally unstable. I was depressed for sure but not unstable, and I didn’t need that label attached to me on top of everything else. I also feared the pills would change my personality. I pictured myself with a stupid grin plastered on my face 24/7, laughing at lame jokes instead of rolling my eyes like I normally would. On top of that, I assumed any happiness I might feel while on Prozac would be chemically induced and therefore fake, rendering it impossible to tell if I was making real progress. Finally, to me, pill popping was a sign of weakness. It was only my eighth visit, and I wanted to try to cure my depression with good old-fashioned therapy before resorting to mind-altering drugs.

  But four months later, after major bouts of insomnia and the inability to concentrate on anything but my gender conflict, I found myself in Bet’s office asking her to tell me more about this wonder pill. She assured me it would not change my personality—that I wouldn’t really notice when it kicked in—but that soon I would just start feeling better overall and life would go more smoothly. The main reason she thought it would benefit me was that it would help stop me from feeling “stuck” all the time—it would free up my mind and keep me from dwelling on things. I’d still feel the full range of emotions, including sadness, but I’d be able to move on from those feelings, focus on other things and be better able to problem-solve.

  “Okay, I’m in,” I said with new hope. Since clinical social workers are not licensed medical prescribers, Bet referred me to a psychiatrist who, after a one-hour evaluation, agreed Prozac would help me. I left his office with a prescription and directions to the nearest CVS.

  “I got the goods!” I announced to my parents as I came home after work that Friday, shaking my bottle of pills. I was told to take one the same time every morning after breakfast. Since it was the weekend, I woke up later than usual and took my pill at around 11:00 a.m. It didn’t strike me until Monday morning when I came downstairs ready to leave the house at 8:15 that to keep on the same schedule, my Prozac would be accompanying me to work.

  “Wait!” Mom yelled, opening the kitchen cabinet that held all the cough syrup and aspirin. “Here, I’ll dump out this bottle of Tylenol and you can put your pills inside.”

  “Mom, it’s fine. I’ll just keep it in my drawer.”

  Too late. The Tylenol capsules were already clacking and scattering all over the counter.

  “No, no, no, this is better,” she insisted.

  “Jesus Christ, Nance!” my dad yelled. Finally, the voice of reason. “What if she forgets and takes a couple when she has a headache?”

  What the what?

  Dad turned to me. “Here, give me that bottle,” Before I could blink, he’d snatched it out of my hand and grabbed a pen. “I’ll just cross out the word ‘Prozac’ so you can’t read it.”

  I stood there watching the two of them argue over the best way to conceal my new prescription-drug dependency, and instead of getting annoyed, I actually found myself smiling.

  Hmmm . . . it’s only been two days . . . could the Prozac be kicking in already?

  No, but six weeks later I began noticing subtle differences that could only be attributed to the medication. Actually, other people noticed and pointed them out to me. They said I looked “refreshed” and “more relaxed.” I realized then I had been sleeping better. When I went to bed at night, I was no longer lying there awake for hours stewing over my gender situation and imagining the worst. I’d still think about it—the issue didn’t magically disappear—but like Bet promised, I was able to move on. Same thing during the day: My problem was still there, but I wasn’t obsessing over it anymore. I was able to focus on other things. I started going out with friends again. Friends I had previously distanced myself from during my suicidal days so they wouldn’t feel hurt or miss me when I was gone.

  Things were looking up and my parents seemed relieved, especially when I told them I was thinking about moving out. A few months prior, three of my best friends from high school had rented an apartment in Cleveland Circle near Boston College and asked if I wanted to move in with them. They needed a fourth and to my family’s surprise I declined. I just couldn’t do it. Not in the state I was in. These friends were girls. I didn’t want to be part of the whole “girls living together” mentality anymore—with siblings or roommates. It was bad enough I spent my high school and college years sharing a car with my sisters that, thanks to my Dad’s clever wit, bore the license plate “GIRLS 3.” I was officially done lumping myself into that category. I also didn’t want to have to explain my whereabouts if I was at therapy or make excuses for why I was crying in my room.

  Now here I was talking about getting an apartment with a friend. The difference was this friend was a guy.

  Jim was one of my best friend’s boyfriend’s best friend. (Got that?) We had started hanging out in a group, mainly at parties when we were all home on breaks from college. He was a good guy, a bit quiet, but had a great sense of humor and was able to keep up with my friends and me when it came to beer chugging and movie quoting. When he started to ask me out separately, I knew where things were headed. I tried to politely dodge bullets and shield myself from advances. One time I even made my mom stand in the hallway to squelch a goodbye kiss that I sensed was in the works. Things were getting too close for comfort, and I was happy to escape back to Colgate for senior year. A week or two later I got a letter from Jim confessing his feelings for me and wanting to know where I stood. I felt I needed to be honest, but what could I tell him? It’s not you, it’s me . . . I’m a guy. I don’t think so. I spent hours crafting my response, letting him know I didn’t share those feelings but that I really valued his friendship. Cliché, I know, but it was the truth.

  I didn’t hear back from him.

  When I came home after graduation we saw each other at a party. It was awkward at first, but over time things fell back to normal. We gradually began hanging out again, watching football, going to pubs, and shooting pool. We complemented each other nicely. He taught me how to shotgun a beer and play darts. I taught him the rules of 7, 11, or Doubles, and that wearing sweatpants out to dinner was unacceptable. When he started talking about wanting to move out of his apartment and finding a new place closer to where he worked, the opportunity seemed too perfect.

  I ran my idea by him and his eyes lit up.

 
; “Roommates, Jim. Nothing more.”

  “Don’t flatter yourself,” he said. “Are your parents gonna be okay with this?”

  Why wouldn’t they be? We’re both guys. “Oh yeah, they’re fine with it. They know we’re just good friends.”

  While Jim was impressed with Mom and Dad’s “progressive attitude,” I was impressed with my own progress. Getting out of my parents’ house and getting on with my life independently was a huge step forward. Looks like I wasn’t “stuck” anymore.

  WORKIN’ IT

  March 11, 1993

  Sitting uncomfortably in the black leather and chrome guest chair inside Ron Lawner’s office, I couldn’t help but feel intimidated. Ron was the Chief Creative Officer at Arnold, one of the top ad agencies in Boston, and would eventually become the creative guiding force behind the award-winning “Drivers Wanted” campaign for Volkswagen. Right now he was interviewing me for the junior copywriter position that had just opened up. Poised behind a sleek desk in one of his signature black t-shirts (which probably cost more than my total income), he silently flipped through my “book” of spec ads, each one suddenly seeming lamer and lamer to me by the second. He chuckled at a TV spot I wrote for Safe Sun, a sunblock product I’d made up, which I thought was a good sign. But by the fourth ad in the campaign, he just turned the page. Damn it! I knew I should’ve stopped at three. The page turning got faster and faster until he finally closed the book and said, “Well, you’ve got a few good ideas in here. When do you want to start?”

  “You mean I’m hired?”

  He looked at me like, “Duh.” Apparently I was the only one who thought there was a chance I wouldn’t get the job. While I’d interned in the creative department at Arnold the summer before and was told I was a pretty good writer, what got me this interview was my connection to the agency’s owner and CEO: my father.

  I wasn’t crazy about the idea of working at my dad’s shop. The slightest whiff of nepotism made me uncomfortable. But after objectively evaluating all the agencies in town, I liked Arnold the best. Plus I didn’t plan on working there very long. I was going to move away when I transitioned, so I just needed a job to last me the next year or two. And I knew I couldn’t stick with my current job as a PA much longer. The early call times, long days, and lousy pay were necessary evils if you wanted to be a producer, but I was more interested in coming up with ideas for spots than figuring out how to make them within budget.

  I had told my dad I wanted to go about this the right way; I was going to take creative concepts classes and put a book together just like every other aspiring copywriter. He agreed with my plan, adding that he wasn’t going to have the company just create a job for me, and he didn’t. Nine months later one finally opened up, and as I was accepting it, it suddenly occurred to me that despite my writing skills and all the time I spent putting my book together, there was a pretty good chance the only reason I got this job was because my last name was the same as the CEO’s. Seeing that Eskandarian isn’t all that common, it also struck me that it was highly likely everyone else at the agency would know I was related to “Big Ed” and, as a result, question my ability.

  That night I asked Dad if he’d told Ron he had to hire me.

  “I told Ron when a position for a junior writer opened up that I wanted him to consider you for the job—to meet with you and look at your book. After that, if he didn’t think you had any talent, he didn’t have to hire you.”

  “I doubt he would tell you your kid had no talent.”

  “Well, that’s what I told him,” he snapped.

  Shit, now I was sounding ungrateful.

  “Listen,” he said more sympathetically, “because of me, you’re gonna have to prove yourself—it goes with the territory. Just work twice as hard as everybody else. And don’t complain. Once they see you’ve got talent, it won’t be an issue.”

  I tried to keep that in mind when I showed up for work that first day, but the fear of being judged and not being able to measure up lingered in the back of my mind as I met my fellow creatives. There were forty in the department, ranging in age from early twenties to early fifties. Most people were friendly, but I did notice that many conversations came to a screeching halt when I approached. Did people honestly think I was going to run and tell my dad everything that happened around here? That Dad and I sat at the dinner table every Sunday going through the department list and making black marks next to anyone who said anything negative about the agency? Besides the ridiculousness of the idea, I couldn’t see that there was even anything to complain about.

  I got in before 9:00 a.m. because that’s when Ron got in, but everyone else strolled in around 9:30. And you could come and go as you pleased, which was a new concept for me because as a PA, I had to report my whereabouts every five minutes. After a week of stopping by my department manager’s office to tell her when I was leaving for lunch or stepping out to go to “an appointment” (therapy session with Bet), she finally said, “Kris, you don’t have to check in every time you need to go somewhere. Just go. You can manage your own schedule.” I immediately left the building to go buy a pack of gum. Just because I could.

  Another bonus: Unlike the rest of the agency, as a creative you could wear whatever you wanted—a big reason I was drawn to this side of the business: No skirts required. While some creatives chose pajama bottoms and flip-flops, my androgynous wardrobe of jeans and Ralph Lauren button-downs became my uniform. You could also skateboard to meetings, play corn hole in the hallways, and at 4:00 p.m. sharp swing by Goransson’s office for his infamous “rose martinis” made with gin and a splash of Chambord. Yeah, I’m liking this job.

  I liked the Arnold culture even more. Every Friday was “Sunset Lounge,” which meant beer, wine, and snacks for all three hundred employees at 5:00 p.m. In the summer you got every other Friday off. You also got your birthday off as well as a bunch of extra days around the holidays. And while this was hardly the era of Mad Men, our Christmas parties and summer outings could rival a few episodes. A source from Boston’s renowned Bay Tower Room reported that the Arnold Christmas party of 1996 had the highest recorded bar tab in their history. The day after every party, you’d find out who won the “Lampshade Award.” That year the decision was obvious—I just thank God it wasn’t me.

  Fun and games aside, what made Arnold so special was the bond that came from feeling both proud and lucky to be working there. We were a tight-knit bunch and for the most part, everyone treated each other with respect. It truly felt like we were a family—one that was led by a well-respected CEO who cared about each and every member.

  Per that CEO’s advice, I worked my ass off, taking all the jobs nobody wanted without complaint. My first real assignment was writing headlines for supermarket circulars and those plastic dividers at the registers that separate your groceries from the person’s behind you: No cash. No check. No problem. Now that was a stellar piece of copy. When my mom first saw it in action at the grocery store, she held up the divider and announced to everyone in line, “My child wrote that!” Somehow that long, skinny piece of plastic managed to wedge its way into one of her grocery bags. She thought I would like it for my office.

  Then there was the catchy line I wrote for the meat department: No one can beat our meat. I had included it among a list of other options as a joke, but the account person never caught it and the client ended up featuring it in a giant banner over the deli counter. Apparently a few customers got the joke and didn’t think it was very funny. It was pulled down three days later. Oops.

  After six months on the job, I graduated from a cube to an interior office, where Ron found me one night while “making his rounds” (i.e., popping into creatives’ offices to see what they were working on or, according to my department mates, seeing who was still hard at work after 6:00 p.m. and who had gone home). His eyes focused on the wall to the left of my desk, where the back-to-school ads I had just brainstormed with my partner were hanging. Rough tissue layouts represent
ed our best attempts at peddling Trapper Keepers and other school supplies for a local retailer, including another ad I had written for laughs, which Ron was now slowly reading out loud for dramatic effect.

  “Is that a pencil in your pocket, or are you just excited for our back-to-school sale?”

  “That one’s a joke,” I said, sheepishly.

  “I like it. You could make a campaign out of it. You know, is that a ruler in your pocket? . . . A protractor in your pocket?”

  Oh my god, this was amazing! Ron Lawner likes my idea and is concepting with me. “Really, you think so?”

  “No.”

  He then smirked and sauntered out. Great, any points I earned for working past six were just nullified by my stupid “pencil in your pocket” line. I soon learned this was Ron’s sense of humor and that he messed with everyone that way. Still, I was glad he never made his rounds while I was concepting the Blue Cross Blue Shield ad for the Braintree Hospital charity golf tournament. I’m not sure what he would have thought of The one time you won’t tense up seeing a doctor put on a glove. The clients loved it, though, and soon the local healthcare provider became one of my main accounts. When it came to creative, they got “it” and my sense of humor.

  Even better, on the agency side, so did the team’s account manager and traffic manager. Beth and Mandy were my age and a blast to work with. Beth had a warm smile, a face full of freckles, and an Ann Taylor frequent shopper’s card. She was by far the most professional of the three of us. Mandy had staggering blue eyes, long blonde hair that by three o’clock was usually pulled back in a ponytail, and a laugh that could be recognized from the other side of the floor. The three of us were inseparable.