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  “Soooo . . . hypothetically, if I were to ask you out on an official date, would you say yes?”

  Jess laughed, “Ah, that’s not really the way to ask someone out on a date, but yes, I would say yes.”

  My heart jumped. “Okay, well, I’m kinda new at this,” Are we flirting? “I have to be in Chicago in a couple weeks for focus groups. I thought maybe I could take you to dinner while I’m in town.”

  “It’s a date,” she said.

  Turns out the hotel where I was staying was just a few blocks from the law office where Jess was clerking, so I gave her my room number and she met me there after work. She looked as beautiful as I remembered and her blue eyes went wide when she saw me. We hugged each other, longer and tighter than what would be considered platonic. As she let go, she said that now it felt “right.”

  I knew exactly what she meant. I was never comfortable hugging anyone when I had boobs. Even though they weren’t that big, they were there like two foreign bodies always in the way and always reminding me I was the wrong gender. I figured I was the only one who noticed it, but I guess Jess had always felt my male energy. And now with my flat chest, that energy matched my physical body. I was just surprised to hear her verbalize it the way she did. I was even more surprised to see she’d brought an overnight bag. She was going to change her clothes for dinner and figured since her office was so close to my hotel it would be easier to just stay over than drive all the way home.

  I didn’t want to be presumptuous but this was shaping up to be the best first date ever.

  We went to an Italian restaurant, drank a bottle of wine, and caught up. I asked her about lawyer stuff and how her family was doing. She asked about my family and kept telling me how great I looked and how much happier I seemed. She too said I looked taller. I told her she didn’t have to flatter me if she was trying to get lucky. I was a sure thing.

  Now for those of you expecting an E.L. James-esque account of what went on in my room, you will be extremely disappointed. This is not Fifty Shades of Grey. The truth is, while I was happy with my body from the waist up, I was nowhere near comfortable with it from the waist down, so our night together was strictly PG, as in “Pretty Great”!

  The following months with Jess, however, were rated G, as in “Gone.” She made a few trips out to Boston but split her time between me and her sister, who was attending graduate school in Cambridge. I began to notice I always got the short end of the stick. Her calls became less frequent and mine were rarely returned. I tried to tell myself she was just busy. I knew the hours lawyers were expected to bill. I’d read The Firm. But it was getting old. And I was tired of feeling hurt.

  Then I hit my breaking point.

  With two days’ notice, Jess called to tell me she was visiting her sister for the weekend and asked if I’d be around. I said yes and that I’d love to see her Saturday. She said she’d call me Friday. I never heard from her. On Sunday morning she called to see if I could meet her for lunch and then drive her to the airport. Even though I was pissed, I agreed. I figured we could at least talk and I could get some things off my chest. When I showed up at the restaurant, I was stunned to see Jess’ sister and her boyfriend sitting at the table. I ate my chicken club silently fuming and feeling like I was just being used for a ride to Logan. On the drive there, Jess said the next time she came, she’d carve out more time for me.

  “Something tells me there won’t be a next time,” I said.

  She looked surprised. “What do you mean?”

  I went off. I told her it was obvious she didn’t want to spend any time alone with me and that whatever romantic feelings she’d had for me had clearly changed. I strongly suspected there might be someone else, but kept that to myself—mainly because if there was, it would’ve killed me. I told her I was tired of being blown off and, without giving her a chance to respond, ended the conversation and whatever was left of our relationship with five words:

  “Don’t ever call me again.”

  I said those words partly out of anger and partly because I felt to get over her I needed to take back control. The only way to stop myself from sitting around waiting for her to call was to tell her not to. That way I wouldn’t have any expectations. It worked for a while, but those words haunted me. I’m not a mean person. I’d never cut anyone out of my life like that before. Around six months later I had a terrible nightmare that Jess died and I was wracked with guilt for leaving things the way I did. I dialed her work number. Her assistant asked for my name and then put me through. I felt immediate relief when I heard Jess’s voice say hello in her normal cheerful manner.

  “Jess, it’s Chris . . . Edwards.”

  “I know,” she said warmly. “How are you?”

  “I’m good. I, I had a bad dream about you and just wanted to make sure you were okay and um . . . not dead.”

  “I’m fine.” I could hear she was smiling.

  I told her I’d been feeling really bad about the way I’d left things and that I said what I said because I needed to get over her. She said she understood and we ended the call both feeling better.

  Hanging up the phone, a calm washed over me. I can’t say I was truly over her, but I was finally able to let go of the fantasy of spending the rest of my life with her. It was time to look forward and open my heart to the possibility of a real, tangible relationship—one that didn’t exist in my head. It was something I definitely longed for; I just wasn’t sure I was ready to put myself out there again.

  Until I met Lucy.

  ••

  You know that saying, “Never fish off the company pier”? Well, it doesn’t apply to ad agencies. Arnold, like many other shops, was extremely incestuous. There were indiscreet make-out sessions at Christmas parties, rumors (both confirmed and unconfirmed) of interdepartmental off-site hook-ups, and full-on dating right out in the open. Lucy and I fell into the last category.

  Lucy was an “Ass Pro” or assistant producer, and our romance bloomed while on a shoot in Sydney, Australia, in 1998. I was producing major TV spots for a financial services company, one of which was going to air on the Super Bowl. As a senior writer, I was in way over my head. The spots relied heavily on computer-generated imagery (CGI), with which my partner and I had little experience. We were also solely responsible for the print and radio campaigns as well as an internal marketing effort for the company. The fourteen-hour time difference was killing us, we weren’t seeing eye to eye with the director, and during a critical juncture in the shoot, the producer we’d come to rely on had to fly home due to a family emergency.

  Lucy ended up being my confidant through it all. She was only twenty-three, six years younger than me, but I found her wiser than her years. She had a boyfriend she was lukewarm on, but I still didn’t think she was interested in me. I thought maybe she looked up to me as a senior creative or big brother type, but discovered she’d had a crush on me a year earlier when she was an intern. She’d seen me give a presentation and thought I was cute and funny. She had no idea I was transgender until she was officially hired at Arnold. Apparently that piece of knowledge freaked her out a little and caused her to keep her distance, but after four weeks with me in Sydney, she fell victim to my charms.

  When word of our relationship spread around the office, people treated both of us differently. Lucy was hot (think Evangeline Lilly as Kate from Lost), so I had instant credibility with the guys. Dating Lucy also changed the perception of other girls who, like her, might have initially been freaked out by my gender history. I now had validation on both fronts. It was a win-win.

  Lucy’s experience, however, was not quite so positive. She was barraged with questions, but not the ones you’d think. They were less about what it was like dating someone who was transgender and more about what it was like dating the CEO’s son: Do you ever have dinner with Ed? Have you been to the Cape house? Coworkers began excluding her from bitch sessions because they were afraid she now had a direct line through me to the top. I told he
r not to worry—that I went through the same thing when I first started and it would wear off. I also warned her people might now say things to her on purpose in the hope that it would get to my father. That happened to me a lot.

  But working together wasn’t why our relationship ended after just eight months. Unfortunately for Lucy, she was my first “real” girlfriend. So while most guys would have had lots of practice by age twenty-nine, I was making high school mistakes. At parties and social events, I was my same outgoing self—talking to everyone, dancing with everyone. I didn’t expect I was supposed to adjust my behavior because I now had a girlfriend. I figured that was my personality and what she liked about me. And due to my gender history, I tended to have mostly female friends. Lucy and every woman I’ve been with since has had trouble with this at some point. They think: Why does he need to hang out with other girls now that he has me? You can see how this might cause problems.

  Then there was our age difference. Six years isn’t that much, but twenty-three and twenty-nine are two very different life stages. I figured Lucy was so young she wouldn’t be looking for a serious relationship, which was perfect for me because I was just starting to date. I was wrong. She was looking for long-term commitment, and I couldn’t give it to her. Nor could I give her the intimacy she needed. I had declared my body from the waist down off limits, which made “sexy time” very one-sided. I figured no woman would complain about that—all the more focus on her—but I learned from Lucy there needs to be mutual give-and-take for a physical connection to be an emotional one. Someone more experienced probably would’ve gotten that.

  Looking back though, the defining factor was the L-word. I remember the exact moment when Lucy told me she loved me. We were in my car. I was dropping her off at home and out of the blue she blurted it out. I froze.

  “You don’t have to say it back,” she said. “I just thought you should know.” Then she smiled and got out of the car, closing the door behind her. I waited to make sure she got in okay and knew I was in trouble when she walked right into the house without turning around and waving to me like she usually did.

  “I’m an asshole,” I thought as I drove off.

  The fact was I did love her, but I was operating under the fucked-up notion that you weren’t supposed to tell a person that unless you knew he or she was “The One.” Someone with more dating experience probably would’ve known that too.

  Lucy tried her best to pretend like my silence didn’t bother her, but it did. We broke up soon after. It was then that I told her I loved her but hadn’t said it because I wasn’t sure I wanted to marry her. She looked at me like I was crazy and informed me that she wasn’t sure she wanted to marry me either. So naturally we got back together. Only to officially call it quits a month later.

  I knew it was the right thing but I still felt sad and empty afterward, fearing there would never be another girl as open-minded as Lucy who would accept me and my “transgenderness.” It was the one thing about my transition that I couldn’t control.

  TAKE MY UTERUS. PLEASE.

  January 1997

  I was wearing jeans and a navy cashmere sweater when I caught her staring at me. She was cute—blonde, mid-twenties, funky glasses. She returned my smile with a disdainful glare and went back to reading her magazine. I guess I shouldn’t be surprised, seeing that I was a guy sitting by myself in the waiting room of the Women’s Health Center for Excellence. I felt more out of place than I did in my pediatrician’s waiting room. At least there I wasn’t on the receiving end of sisterhood animosity.

  Many transgender men view the hysterectomy step as unnecessary—the testosterone has already stopped the periods from coming so why bother? It’s just more invasive surgery and a lot more money to pony up, as insurance likely won’t cover it without a documented cancer diagnosis. And once it’s all over, it’s not like you can physically tell or feel any difference.

  I can’t speak for anyone else’s choices, but I can tell you why I felt so strongly about having the procedure: I wanted everything feminine about me gone.

  Even something as seemingly minor as the tiny holes in my ear lobes. While they had partially closed up, you could still tell they had been pierced, and I became very self-conscious about it during my transition phase with my sideburns and shorter haircut.

  I’d overheard my editor telling a client about how her earlobe had torn from wearing heavy, dangly earrings so much. She said she found a great plastic surgeon just a few blocks away who stitched it right up. It was quick and painless and didn’t leave a scar. I mentioned this to my parents who talked me out of it, saying I was crazy—that no one could even tell my ears were pierced to begin with. Then one day at lunch I caught Babs staring at me with a quizzical look on her face.

  “Shtiny, do you have pierced ears?”

  That’s it. I’m making an appointment.

  The next week I found myself face-to-face with my editor’s plastic surgeon, ready for the twenty-minute procedure. He said he would be using extremely fine stitches on the inside and that the most anyone would ever see (if they were up real close) would be the tiniest vertical hairline scar and even that would fade away over time. What he failed to mention, however, was that I’d be walking out of his office looking like Frankenstein, which is what a friend of mine called me when she spotted me on my way home. She saw the zigzagging navy blue thread used on the “surprise” exterior stitches and asked what the hell happened. I told her I had cysts removed, which is what I continued to say for the next week until the stitches came out. Funny, I had no trouble telling people I was having my uterus removed but needed to make up a story about getting rid of ear-piercing holes. Maybe it was because they were visible to everyone and my uterus wasn’t.

  Regardless, just knowing my reproductive organs were there made me uncomfortable. I didn’t want to have to see a gynecologist for pelvic exams and pap smears and worry about getting ovarian, uterine, or cervical cancer down the road. Those were women’s issues and I wanted nothing to do with them. I wasn’t sure I wanted children, and even if I did, as a man I wasn’t about to get pregnant and give birth even if I had the capacity to do it. As far as I was concerned, all those “female parts” inside me had the potential to do more harm than good both physically and emotionally. My parents eventually understood and once again Mom said she’d take care of me and Dad said he’d take care of the bills. It was not lost on me how lucky I was. Still, luck wasn’t doing anything to shield me from the suspicious looks I was getting from the other women in the waiting room and I eagerly gave up my seat for a private one inside the surgical gynecologist’s office.

  My surgeon came highly recommended by Dr. D, who had, to my relief, already filled her in on my special circumstance. She had a professional, buttoned-up demeanor and an extra-firm handshake. There was no small talk or joking around. She launched right into all the procedural options, outlining the difference between a hysterectomy (uterus) and total hysterectomy (uterus and the cervix) and then asked me if I wanted to keep my ovaries. I had assumed they were part of the whole reproductive apparatus and would be removed along with everything else. She said most people think that too but that it’s actually a separate procedure. She asked if I wanted to have children or harvest any eggs to be frozen for future use. I passed on both options. If I ever did decide to do the kid thing, I wanted it to come from my wife’s eggs. When the doctor asked me what I’d do if my future wife turned out to be infertile, I told her I’d cross that bridge when I came to it. At this point in my life I had no girlfriend and no interest in having kids; the last thing I wanted was to be responsible for another person. I’d been living the last twenty-seven years of my life for other people. I finally just wanted to focus on myself.

  We mapped out my surgery, deciding on a total hysterectomy and salpingo-oophorectomy, which would remove all female reproductive organs and eliminate any future need for gynecological exams. She told me the surgery would take an hour or so and that I might not ne
ed to stay overnight. I’d have a horizontal scar across my lower abdomen resembling that of a C-section (today the procedure can be done laproscopically with very little scarring), and the recovery time would be about four weeks. I set the date for January 1997 and looked forward to starting the New Year uterus-free.

  ••

  When I woke up, I didn’t feel nearly as bad as I did after my mastectomy. I wasn’t even nauseated, which was a huge relief. I felt a hand squeeze my arm.

  “Hi, Shtiny.”

  My mom was there—an even bigger relief. I tried to sit up but my abdomen wasn’t havin’ it. I surveyed my surroundings. It looked nothing like the curtained-off section I had in recovery at the last hospital. I had my own private room! I was amped until Mom informed me that yes, it was a private room, but no, I was not in recovery. I was here for the night—possibly two.

  What? I asked her if something went wrong with the surgery.

  “No,” she said. “It didn’t even take an hour.”

  So what was the big deal? I had endured a nine-hour bilateral mastectomy and went home that same evening. This surgery took under an hour and relatively speaking, for someone who’d just had his insides scooped out, I felt pretty good. My mom agreed that it was ridiculous but my doctor went “by the book” and most patients after a hysterectomy are in the hospital for two to three days.

  When Dr. By-the-Book came to check on me, she was all smiles. She said my surgery couldn’t have gone better and that it was the fastest hysterectomy/salpingo-oophorectomy she’d ever performed. Apparently sixteen months of testosterone injections had shrunk my entire reproductive system to the size of a fifty-cent piece, making it extremely easy to remove. (Why I was left with a twelve-inch scar is still beyond me.)