How Jennifer Aniston Got Me Through My Breakup

Photo: Matt Baron/BEI/REX/Shutterstock
This is an extract from So Here’s the Thing: Notes on Growing Up, Getting Older and Not Giving a Shit by Alyssa Mastromonaco.
Like most people, I have problems. The problems are not insurmountable, but they’re sometimes unavoidable. Like many people, I deal with them by zoning out and watching TV. I developed this habit during my freshman year of college—when I was under the impression that I was the least cool and smart person in my dorm—because my arrival on campus coincided with the debut of three major shows: My So-Called Life, ER, and Friends.
In my dorm, Chittenden Hall, My So-Called Life became a common-room event. Maybe because thinking Jared Leto is hot is an equal-opportunity pastime. Jared Leto in 1994 can appeal to all genders and sexual orientations. I made some new friends from other floors during our watch parties and slowly realized that watching a very insecure, confused, and probably depressed Angela made it easier for us to talk about similar shit. ER, meanwhile, was the opposite of relatable: It was exciting and wonderful because George Clooney was exciting and wonderful. His love story with Nurse Hathaway (Julianna Margulies) was more tortured than Romeo and Juliet. Also, I love hospital shows because it’s basically like watching WebMD: You might not admit it, but you start to self-diagnose before the first commercial break. But the show that made the most lasting impact on me—as in it triggers something besides confused nostalgia about an emotionally turbulent phase in my life or yearning for George Clooney—was Friends.
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Friends was on Thursday nights, which was also pre-weekend party night at UVM and many other colleges. Luckily, I didn’t like to go out—despite what my sparkling Twitter persona may suggest, I’m easily felled by social anxiety—so what I lost in social capital I made up for in being an expert on this show. I don’t think I missed an episode.
Though I wasn’t a runaway bride and had no iconic haircut, I immediately liked Rachel Green (played by Jennifer Aniston), who, for all her prissiness, often found herself in the kind of scrapes I could relate to: foot-in-mouth miscommunications, imbalances between expectations and reality, and disliking things before she got to know them. A couple of years later, when it came out that Jennifer Aniston was dating Brad Pitt, a man so sexy his name is synonymous with the quality, I became obsessed.
Along with my weird attachment to her character on Friends, I tracked every detail of Jennifer Aniston’s relationship with Brad Pitt in the tabloids I was still ashamed to read. I remember the moment I heard they were potheads and liked to smoke and go to concerts—I was a pothead who liked to smoke and go to concerts, too! She was so likeable and relatable, yet she nabbed the Hollywood heartthrob. There were fireworks at the wedding!
But the fairy tale started to get dark in early May 2004, when the final episode of Friends—the most-watched episode of the decade, a huge event everyone talked about for weeks afterward—aired in front of a live studio audience. And although it ended up being a dramatic moment of romantic resolution for Rachel Green, apparently Brad didn’t go. I was stricken. WHY WOULD HE NOT GO? Was he filming? Was he sick? Or was it...something else?
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Now, let me state for the record that I am well aware Jennifer Aniston does not need my concern. Intellectually, I know this.

Now, let me state for the record that I am well aware Jennifer Aniston does not need my concern. Intellectually, I know this. But I cared, a lot, and maybe the amount I cared made it difficult for his absence to compute. Had America’s Sweetheart been left at the altar of her Friends finale, like a bizarro inversion of the first episode when she appears in Central Perk frazzled and soaking wet in her wedding dress and veil?!?!?!?!
The unease passed after I watched the episode. It was so emotional! Maybe none of the other cast members’ partners were there—I should have tried to find David Arquette! The cast probably wanted to take in the final moments of this life they’d lived and the world they’d created together. Yes. Maybe that was it. I’d always thought TV shows were a bit like campaigns: You work fourteen-, fifteen-, sixteen hour days believing in what you do but not knowing if people will like it or respond to it, trying to make a compromise between the integrity of the project and its commercial viability/electability. And though the cast of Friends was each making a million dollars an episode by the end, so this isn’t a perfect comparison, it’s true that for many shows you have no job security. You can be picked up or cancelled at any time. Both require resilience and loyalty. And maybe a bit of obstinacy.
Six months later, I was at Faneuil Hall in Boston watching John Kerry give his concession speech. We didn’t see it coming, and it was oddly one of the best speeches I think he’s ever given. (Same with Hillary—her concession speech was second to none.) (Actually, this is also true of John McCain.) Anyway, days later I was on the unemployment line in Anacostia with my friend Terry, and all I could think was that I wanted to go home and rewatch the last season of Friends, which I had on VHS.
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Rumours began to circulate that Brad had been getting cosy with Angelina Jolie, his Mr. and Mrs. Smith co-star and another actress in whom I could find no fault. Shortly after New Year’s, there was a picture of Brad and Jen walking arm in arm—canoodling, actually—on a beach in Anguilla—he was wearing a T-shirt that read TRASH. My fears about their possible breakup were finally assuaged.
Until a day later, when they announced their separation in this statement:
We would like to announce that after seven years together we have decided to formally separate. For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media. This decision is the result of much thoughtful consideration. We happily remain committed and caring friends with great love and admiration for one another. We ask in advance for your kindness and sensitivity in the coming months.
A lot of thoughts were running through my head. Yes, there was the ordinary unnecessary but inevitable concern for Jen. Was she OK? Was this just for PR, or would they really remain friends? And then there was another question nagging me and the rest of the world: WAS THE ANGIE GOSSIP TRUE?!
There was also some self-interest in this fixation. By this point, I’d been dating Doug—who shared some similarities with Brad Pitt in that he was a notable figure in DC, had been profiled by hotshot reporters, and was beloved by the ladies—for about five years. He was basically double my height, handsome, and charming. Women would openly flirt with him in front of me.
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I knew it wasn’t forever. Back then relationships made him feel like a caged animal. Maybe a ferret. He was open about it, and felt guilty about it, but there it was. It was the classic thing where he didn’t want to hurt me, and breaking up with me would definitely hurt me, so instead he tried to mete out the hurt in tiny, imperceptible doses that he felt I wouldn’t notice. If we were going to break up—and we needed to—I was going to be the one who had to do it.
Even when you know you have to do it, breaking up always seems impossible. There’s no good way to start. "We need to talk"? You might as well just skip the rest— it’s obvious where this is going. And when you know the guy is over it and just waiting for you to cut the cord, it’s even worse. He was going to be relieved by whatever I said. There wouldn’t be any effort to resuscitate this relationship, at least not romantically. No begging, though I can’t say I didn’t fantasize about it. And although he was kind of a jerk, romance-wise, I did still want to be friends.
But then I thought about Jennifer Aniston. I know—I am a teenager. But the lesson was that it didn’t have to be all reality TV screaming matches and jealousy. We could get over our issues quietly and not hate each other. If Jen could be OK breaking it off with Brad Pitt and staying friends (allegedly), then I could be OK. The eyes of the world were on her—I just lived in a one-room apartment with my bed eight feet from my oven.
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In totally unprofessional form, I initiated the conversation in the middle of the workday. Since we worked in the same place, this was easy—no text-message breakup here. (Don’t do this!) I got it into my head that I should do it right then, and my mental health trumped professionalism. I needed to not be alone after the conversation, and at work I had Favs and Tommy next to me in the back corner of the Obama Senate office and my friend Terry, who worked for Senator Maria Cantwell, down the hall. As I said in my last book, it happened right as they were announcing the new pope.
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Within days—maybe one day—the ladies had pounced. I stopped being invited to as many parties, but since I couldn’t risk running into some comms intern batting her eyelashes at my ex, I spent many more nights at home than I had before (seriously, I became much less awkward after college and did enjoy going out) with music, tabloids, and yes, some pot. (This was pre–West Wing, it was OK! Well, not OK, but OK.) Also, I wore my TEAM ANISTON shirt from Kitson a lot. Then, inspired by photos of Jen with her dog, Norman, I got a cat, the formidable and irreplaceable Shrummie. Who weighed twenty-three pounds and wouldn’t come out from under my chair for a while.
About a year later, I took myself to go see Jen’s next movie, The Break-Up with Vince Vaughn, in which the two play a couple who have recently broken up but are trying to keep their apartment by continuing to live together as roommates. Though I felt she deserved to have a box-office smash, I didn’t realise until we were in the middle of the movie that she was doing something metafictional: She had made a movie about breaking up (yes, obviously the title should have made that clear to me) while breaking up IRL. And of course Jen and Vince briefly got together while breaking up on-screen. Talk about a mind-fuck. He later said he couldn’t deal with all the attention. I’m glad I’m not an artist and only have to go through emotional turmoil on one level.
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My moment of realization was a scene at a concert. Or was supposed to be a scene at a concert. Although Brooke (Jen) and her live-in boyfriend, Gary (Vince), have already broken up, she invites him to a concert, thinking this will be a clear message that she wants them to give it another shot. (Even though, to be fair, she’s also been bringing men over to the apartment to make him jealous.) They agree to meet there. He goes out drinking with his friends and doesn’t show up, not at all realizing that this is supposed to be a definitive statement on their viability as a couple. But they’re still sharing the apartment, so when she comes home and walks into her room after being stood up, she just can’t take it and erupts into uncontrollable sobs. I knew it wasn’t acting. Even when you’re trying your absolute best to embody "conscious uncoupling" before Gwyneth gave it a name, it sucks.
It made me feel so much better. (Though somehow also worse.) Sometimes the thing that helps you get through hard moments is small, or embarrassing, or doesn’t make sense at all. You might get a cat. You might dye your hair. You might then cut the hair you dyed. You might try the South Beach diet and realize you can spend your nights cutting up vegetables and trying not to think about how you’re going to be cutting up "vegetables for one" while humming "I’ll Be There for You" by the Rembrandts for the rest of your life. Sometimes you sit alone and cry after work after you’ve told everyone how "fine" you are. And despite your best coping mechanisms it can take months or years to get back out there. And that’s OK.
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