Dealing with the inauguration is a little bit like being a bouncer at an exclusive club in New York: Lots of people want in, but only certain people have tickets, and only certain other people have really, really good tickets. We had to make lists, prioritize, and try to make everyone as happy as possible. I found myself meeting people on street corners in Georgetown to exchange envelopes of very valuable goods. Even though I knew I couldn’t go, my family—Mom, Pop, Moose, and Volpes (Cara couldn’t make it because she was in labor)—got prime seats (“seats” being the key word) right in front of the Capitol.
The official festivities kicked off three days before the Tuesday inauguration, and the hottest ticket was the Lincoln Memorial concert on Sunday. Bono would be performing our campaign theme song, “City of Blinding Lights,” which we had picked sitting around a conference room table in Springfield, Illinois, because we loved the intro; great entrance music should give you goose bumps. Beyoncé, Bruce Springsteen, Mary J. Blige, Denzel Washington, Pete Seeger, and Laura Linney would also be performing. Dey and I were at the transition office in DC taking turns jumping up and down so the motion-sensor lights would kick back on.
On Monday night, inauguration eve, Dey and Jess slept over at my apartment because road closures would make it impossible for people to get to work. On Inauguration Day, Dey and I would be sworn in, and then we had to start preparing the schedule and setting up events for the president’s first full day in office.
I met Dey and Jess at my apartment, and my downstairs neighbor, Anne, who was a friend from Chicago, came to join us. We all went to bed early, and in the morning we had Eggo waffles and mimosas and watched the inauguration coverage as we were getting ready—a very surreal sleepover. After Jess went off to man her inauguration post, Dey and I put on our suits, sneakers, and about eight layers to walk to the White House; it was fucking cold and a little slick. We took our dresses for the inaugural ball with us because we thought it would be too dicey to try to get home and come back.
Entering the Indian Treaty Room in the Eisenhower Executive Office Building (EEOB), we immediately found ourselves among a ton of people we didn’t know, a lot of them acting like hot shit. People were scheduled to come in waves throughout the day; we filled out our employment forms with about 30 other new staff. When we stood up, raised our right hands, and were sworn in, it was a pretty standard procedure, but it should have been a real moment. If we hadn’t been so anxious, we might have enjoyed it a bit more.
We parted ways after that. I headed over to the West Wing, and Dey, who was deputy assistant to the president and director of scheduling, went to our offices in the EEOB.
I don’t think Dey and I ever changed out of our sneakers that day. A New York Times article described the feeling of the president’s first full day in office as being like “the first day of school”; for us, it was sort of like that, if not making it to sixth period on time would cause the United States government to screech to a halt. Obama had to do actual things—like have meetings in the Situation Room—that no one around him knew how to facilitate yet. We found out there were protocols for using certain rooms (i.e., the Cabinet Room is only for meetings with the Cabinet or congressional leadership), and figuring them out took so long. Some rooms you couldn’t use for live press events because the copper wiring blocked signals. How do you book a meeting in the Situation Room? What kind of security clearance did people need to have? We didn’t even have computer log-ins. When someone came in to teach us all how to use Timepiece, the software that allows you to make the White House schedule, I almost cried. It was impossible, and we had to use it that day.
We’d had the campaign down to an actual science. We had managed our department’s $68 million general election budget within dollars and were able to go to Plouffe that fall and tell him he could take money back because we were on track to come in under budget by $3 million through the end of the campaign. (Anytime you can tell your boss or someone higher up that you have saved them money, do it.) We planned about three events a day, seven days a week, and that was just for POTUS. By the time we hit full speed after the convention in Denver, we were managing Barack, Michelle, Biden, Dr. B, and a slew of other high-profile surrogates like Ted and Caroline Kennedy, Jay Z, Bruce Springsteen, and Oprah. Except for the time we accidentally played Kanye West’s “Touch the Sky” at an event for senior citizens a few weeks before the Iowa Jefferson–Jackson Day dinner, we ran like a well-oiled machine.
But this? This was hard. There were so many rules and protocols for the White House: Noncommissioned officers’ names cannot appear on memos to the president; cabins on AF1 are ordered by seniority, and you can walk back on the plane but are not supposed to walk forward into a more senior cabin; in the Cabinet Room, the president always sits with his back to the Rose Garden in the chair in the middle with a slightly higher back, the vice president sits across from him, and the Cabinet secretaries representing the oldest departments—like State and Defense—have to go closest to the president. Just when you thought you had them all in order, someone came to you with more rules. The dress I was supposed to wear to the inaugural ball stayed in its bag in my office for two years. I never put it on and actually forgot it was there.
I am making this sound Very Bad partially because I did not expect it to be so bad. This is what the president’s first public schedule looked like:
1:15PM: President Obama addresses staff and Cabinet secretaries (pool press)
2:30PM: President Obama attends White House open house (pool press, base of staircase, on the ground level by State Room)
3:15PM: President Obama meets with economic advisers in the Roosevelt Room (closed press)
4:15PM: President Obama meets with Iraq military advisers (closed press)
That’s it. This is the schedule that kept me from getting to the inaugural ball the night before. This.
It wasn’t all chaos; we learned some fun things, too. For example: The current Cabinet Room table was purchased in 1970 by President Nixon using personal funds. On her very last day in the White House on January 19, 1977, Betty Ford passed by the empty Cabinet Room and decided to take off her shoes and dance on it because she had always wanted to.
People were telling us stuff like this as we were trying to find the appropriate room for the president to address senior staff and Cabinet members on his first day. We didn’t want to send out the schedule with the wrong room, and it was so hard to get all the protocols straight that it took a very long time.
When we finally thought we had figured it out—and when we got our computers up and running—we sent an email to the senior staff to lay out our plan. One member of the team, who we were pretty certain was writing to us from a cush seat in the presidential viewing stands at the inaugural parade, responded, “This is the most half-baked thing I have ever seen.” And we didn’t even know why.
We finally figured out Room 450 was an acceptable solution and called it a day at around 8:00 PM. Dey left in the nick of time to meet her boyfriend and slog through one of the inaugural balls. I walked home—not because I wanted exercise but because the roads were still all closed; it was freezing, and the streets looked like a scene from a Cold War movie. I ate a Lean Cuisine, slammed a glass of wine, and wondered what the hell could be in store for tomorrow.
There are moments when you catch yourself wondering how you look walking off Marine One—wind blowing in your hair, serious leather bag at your side, adjacent to the man who runs the country. There are also times when you actually walk off Marine One with the president on a Friday afternoon in rural Virginia, climb into your armored Suburban, and are told by a member of the medical team that you have split your skirt clear up to the zipper. Those are the moments you should remember: when your coworkers are rallying around you to keep you from showing the president your really old Hanes Her Way underwear. When they pin you together and you have to lie sort of sideways in a mermaid position so you don’t bust the pins.
This is not an e
laborate scenario I made up to illustrate the importance of humility—it really happened. I attribute a lot of my success to never losing sight of the fact that I worked for Barack Obama. I was not Barack Obama; I am never going to be Barack Obama. In DC, you can get some level of power from the person you work for, but the minute you forget power comes and goes with elections, that’s it. You may think you are hot shit for working at the White House, but there is always hotter shit around the corner. You are staff, a helpfully lowly term.
Around six months before David and I got engaged, I went to a dinner being held in honor of UK prime minister David Cameron’s visit to America. It was a big deal; everyone in the White House was excited about it. I would be wearing vintage. David never really cared about stuff like this, so I brought Dey as my plus-one.
The day of the event, David had lunch with Jeff Shell, the chairman of NBC Universal International at the time, and during the dinner, David texted me to say Jeff was there and that I should say hi. I had been to a lot of black-tie events by this point, but the gravity of the company was always a little intimidating, even while I was wearing a fabulous dress and had knocked back a champagne. Jeff was at a table with Anna Wintour and her partner. I tapped Jeff on the shoulder, introduced myself, and said I’d heard he’d had lunch with David that day. Jeff recognized me immediately. “Oh,” he responded warmly, “David’s the best. You guys are going to be just like Susan Sarandon and Tim Robbins, living together forever but never getting married!”
Everyone froze. “Oh dear,” Anna said, looking up and lowering her head in that skeptical way she does. I had been able to pass off other people’s “You’re an old lady who will never get married!” faux pas before, but this was humiliating.
I went back to David’s house at around midnight—we weren’t technically living together, because I went back to my apartment every morning to change clothes before work, but my cat lived at David’s—and I was livid.
“Do you know what just happened to me?” I yelled at the sleeping man.
“What?” he asked, very groggy.
“You told Jeff Shell that we were going to be like Susan Sarandon and Tim Robbins?” I went downstairs and watched TV.
Even after he changed his mind and proposed to me in front of the Georgetown Domino’s, I had a very difficult time accepting that he had come around. Shrummie and I officially moved into David’s place after we got engaged, and I was a wreck. I wish that I had tried to live with a boyfriend sooner than age 37, even if I knew we would probably, eventually break up, because I was deeply, almost bizarrely uneasy about moving in with David. I felt like a burden, or an intruder, or like I’d tricked him into proposing to me. I kept my apartment, still paying rent, for about eight months after I moved in with him. I also kept all my Crate and Barrel furniture there, just in case; David had much nicer stuff, but I never felt like it was mine, and I didn’t feel like I could bring any of my things to the house because all my things were from Crate and Barrel. I cried a lot.
When we got married, it was even harder, because it was legal. I couldn’t get over the money thing, and instead of a little nagging sense that I was barging in and toppling over David’s high-flying bachelor lifestyle, the marriage made our relationship feel officially imbalanced. What could I possibly be adding to our life? I was constantly doing calculations in my head, thinking about how much the impressiveness of my job at the White House, or my skill at making granola, or my cat, was potentially “worth” to my husband—like I was trying to tally up a bizarro-feminist dowry. I had a savings account without much in it, and for probably eight years, I had done all my finances in a Barbra Streisand notebook; when it ran out of pages, I just added more. David had an accountant and stock. I guess I would often talk about what I was “bringing to the table,” because one day he told me, “Stop using the word contribute—we are married.”
The actual planning and implementation of the wedding also gave me anxiety, and we didn’t even have a wedding. We were going to, but it just seemed like too much work, especially for two people with very busy jobs. When older people get married, the guest lists are already long, but one night we went to Meiwah and decided to try to sketch out a list of people we would have to invite. It looked like something out of Us Weekly. David’s list in particular looked like a Kardashian who got into politics: Senate majority leader, Senate minority leader, all the way down to staff assistants. He wrote for so long after I was done that I think I ordered another wine. My family would have gotten there and been like, “Who are you? This is ridiculous.” It was my job to plan very elaborate and stressful events, and I didn’t want anyone to have to go through that for me. We decided to skip a big wedding.
Unfortunately—or fortunately, if you espouse a mergers-and-acquisitions perspective on wardrobes—we did not make this decision before I bought a wedding dress. A few weeks before the Meiwah Accords, I had gone on a short trip to Chicago, and when I met up with Anne, Julianna, and Stephanie Cutter (a friend who had a series of roles in the Obama family), for what I thought would be an afternoon of expensive salads and cocktails, they surprised me with appointments to look at wedding dresses.
It was so, so nice of them, and I was completely mortified. As we walked up the steps to the first shop, I turned to the group and said, “OK, guys, I’m going to do this, but I really don’t want it to be a scene.”
We opened the doors and Austin Scarlett, from the first season of Project Runway, was having a trunk show.
When you watch an episode of Say Yes to the Dress, you don’t see all the scaffolding necessary to maneuver a normal-size woman into a sample-size wedding gown. All of a sudden, the tasteful, elegant person you think you are goes out the window; I was surprised and disappointed to learn that bungee cords would be required to get me into the dresses I wanted to try on. Maybe it says something about how susceptible I am to patriarchal narratives about the lasting importance of a woman’s wedding day, but instead of thinking the whole thing was ridiculous, at one point I found myself in a jewel-encrusted peplum dress with a “vanity sheet” covering my butt, and I earnestly turned to my friends and asked, “How do I look?”
Awful. I tried on some Jenny Packhams, which made me feel like Princess Kate, and then we went to Vera Wang. Vera gave us champagne, which helped, but the dresses were heavy and unflattering. I didn’t want to go anywhere else, so I suggested we give up—though it was a fun, nice gesture—and go to Freds, the restaurant at Barneys.
Everyone thought this was a great idea, but I wonder if it was because they knew they could get me drunk. After a couple of cocktails, they were all saying, “Come on, one more place! It’s just around the corner!” I went on the condition that it would be a purely academic excursion and everyone would only pick dresses that it would be “fun” to try on.
This was a much better experience. But when we were about to leave—this always happens—Julianna came back with a beaded, one-of-a-kind Valentino runway and said, “Alyssa, I know this looks crazy, but you should try it on.”
It was $13,000 and I bought it on a payment plan.
I want to pause here to say that buying a $13,000 designer wedding dress was not something I ever thought I would do. When I was growing up, I never dreamed of the perfect wedding or cared much about having the nicest, most expensive things. I also could not really afford it; I had tried very hard to save money while I worked in government, so this was not going to destroy me, but it was still a stupid purchase. Beautiful, but dumb. David later offered to pay for it, but I wouldn’t tell him how much it cost, and I didn’t want him to anyway.
Still, it looked good. We went to the restaurant in Ralph Lauren and had steak Diane to celebrate that I’d bought a dress that costs the same amount as a Nissan Versa.
After we decided to ditch the real wedding, there was still the problem of the venue: Would we just go to City Hall? Would we have even a little party?
I thought we should. But it was not the best time: healthcare
.gov was still failing, and the government shutdown, which happened about a month and a half before I got married, was sapping all my energy. I oversaw preparations for the shutdown as well as for the reopening, and in the middle we had to follow yet more protocols. I came to work because, as an assistant to the president, I was permitted to; most other people couldn’t use their BlackBerries, access their emails, or come into the office. This included the cleaning staff. White House operators recorded a script for answering the phones, something like: “Thank you for calling the White House. Due to the government shutdown, we can’t help you.” It was sort of nice in some ways; you had senior people answering their own phones and doing dirty work, which created this sense of camaraderie. No one acted like a diva. If someone (approved) was coming in for a meeting, I cleaned the bathroom stalls, made sure the garbage cans weren’t overflowing, and refilled the toilet paper.
When it became obvious that planning even the most basic wedding would be too much, someone told me that Elena Kagan and Sonia Sotomayor loved officiating at the Supreme Court. This seemed great. I bought a short Stella McCartney dress from Farfetch (blue with wide sleeves), and we scheduled a Friday afternoon with Justice Kagan, who was glad to have us.
On the day of my wedding, I acted like a savage animal. When people have big weddings, to defuse their nerves, they fixate on the flowers not being right or a bridesmaid being late; when it’s just the two of you, you have to confront your fear and destiny head on, and because I didn’t know how to say I was nervous, I was really mean.
This was totally disproportionate to the kindness everyone showed me. After waking up scared, I went to get my hair done—the first mistake of the day. I should have just gotten a blowout, but the women at the salon told me I should get something different because it was my wedding day. Shortly after, I cried. My friend Stephanie showed up at the salon with champagne and hummus because “you have to see someone on your wedding day.” Even though I wasn’t there, my team decorated my office with a banner that read “Goodbye Single Alyssa” and did a photo shoot with it to show me over text messages. I pay it forward by advising all my friends who get married that, because it is so nerve-racking, they should just drink all day or take a Xanax.
Who Thought This Was a Good Idea? Page 15