Fleishman Is in Trouble

by Taffy Brodesser-Akner

  “Can I go to sleepaway camp the whole summer next year?” Hannah asked.

  “Sure.”

  Solly was silent. He didn’t like talking about sleepaway camp. Rachel had spent much of the early spring lobbying hard for him to go for the month, “like all your friends, Solly,” but he kept saying that he enjoyed being with his parents—“You’re my friends, too”—which made Toby want to weep.

  “Next year,” Solly said, “I want to come back to the Y but I also want to go to golf camp.”

  “We’ll make it happen,” Toby said, though he then wondered if he was raising a golf douche. His mother had always told him to look at his neighbors and ask himself if he wanted his children to turn out like them, because they would. Neighbors, she’d said, were a far more powerful force than parents. Neighbors were how you voted for a child’s future. But Toby hadn’t taken that seriously, because how could his children be like his neighbors when his neighbors, who were all WASPs of sparkling genetics and crystalline breeding, were wholly unfamiliar, and his children still spoke and sang in the echo of his voice?

  They returned home and had dinner—Toby had ordered soup and chicken from the deli, which he hated doing; he knew how much takeout they had with their mother. They ate, and Toby listened to Solly’s report of the day, and how many kids were not returning to day camp after next week but were leaving for sleepaway. Then he let them leave the table and flee to their rooms to do whatever they wanted to until Mona arrived. He cleaned up the dinner and took a shower and began to prepare his body and mind for this woman whose crotch he was now very familiar with. He sat on his bed, a towel around his waist, searching his phone to make sure he knew what her actual face would look like from her Hr avatar, so that he could return her, briefly, to personhood.

  At first, he told the kids he was on “appointments” when he had a date that was coinciding with their night with him. But Hannah began asking questions about what kind of appointments kept happening on Saturday nights, and why he had to change his clothes for them.

  “Are you going to get married again?”

  “I don’t think so,” he said. “Once might have been enough for me.”

  He always told Solly and her the same thing: “I go on playdates sometimes, just like you do. I will tell you when there is someone you should know. That person will be someone you like. I am lonely and I am making new friends, and not all of them will be my girlfriends, but some may be girls who are friends.”

  “Your mom will eventually have playdates, too,” he told them.

  “Will they be with doctors?” Solly asked.

  “No, they’ll be with people who are different from me. They’ll be with a man named Brad who has a Porsche and wears boat shoes and really wants to come to your soccer game.” The kids laughed. “Now: Who am I going to date?”

  And they responded in unison, as he’d trained them to over the course of the many times this question came up: “Someone we will like!”

  “And who will Mom date?” he asked.

  Again, in unison: “A man named Brad who has a Porsche and wears boat shoes and really wants to come to my soccer game.” Solly could never finish that last part because he was always laughing too hard by then. It even got a smile out of Hannah.

  “You’ll like him, too, when it happens,” Toby said, though he didn’t think that was true. If he was honest, he didn’t even know that Rachel would ever date again, so disgusted was she by the confines of marriage, so ruined had she been by the compromises of another person trying to have an equal say or even just an opinion in her life.

  * * *

  —

  TOBY’S USUAL DATING outfit was a pair of gray twill flat-front pants and a tailored light blue button-down shirt. He was still wearing the clothing Rachel had insisted on dressing him in, materials finer than you could find at the Banana Republic he liked on Third Avenue. She liked for him to look like a rich person. (“You are a rich person,” I’d say. “Yeah, but not for long,” he’d say. I meant that he was richer than most people on this earth; he meant that he made $285,000 annually, and that was on the extremely low end for the neighborhood.) But he noticed that his shirts were starting to fray. It was time for new ones, but he kept punting the decision. How do you go back to Banana Republic now, after all that time spent being measured for a shirt by the Italian tailor on Sixty-fifth Street who made clothing just for you? He could afford it, that was the truth; maybe he’d continue to do it, but now it was a choice. If he wanted to take the kids on vacation for winter break, if he wanted to think about buying an apartment eventually. There were decisions to make. “I left a lot of money on the table,” he liked to say to people who knew the situation, to show that peace was more important to him than money.

  He was set to meet Tess at Dorrian’s, a bar on Second Avenue he never went to and only thought of as the hangout for prep school kids in the eighties before one of them murdered another one of them. Dorrian’s was Tess’s idea. Something felt distinctly noir about this, a woman in a wrap dress and mega-cleavage at a bar, dyed blond hair in a twist, him walking in to find her there already with a drink—a martini with six olives—tonguing the cocktail straw, which was a new choice for a martini but he tried not to judge.

  The moment stretched out for what seemed like a month as he waited to see if she found him acceptable. There was nothing glaring about him that would make a woman walk out on him; his only clear abnormality was his height (“and your rage,” Rachel would say). He watched her eyes to see her immediate reaction to realizing just how short five-five actually is. Could he see a glimpse of surprise in her eyes? Concern? Revulsion? He couldn’t, and he was relieved. He was getting good at knowing if this was a nonstarter—the way eyes lost brightness when they were reflecting disappointment; a politeness that was trying to clean up the disappointment; the same wall I put up that first night we met when I realized I couldn’t bear how short he was. He didn’t like to waste anyone’s time, least of all his own, least of all his babysitter money.

  He ordered a Scotch and she told him her story. She had three kids, they were at Dwight, her husband was a banker who, three years ago, went on a life-coaching survival skills weekend. She had sent him on the weekend for his birthday for $10,000. It was led by a renowned life coach/healer who had recently graduated to being a shaman and who could maybe help him figure out why he was so depressed all the time. He had been talking about being on his private jet and wanting to jump out of it. He talked about wanting to make things with his hands, like bread and birdhouses. “Good, good,” Tess said. “Go off and come back to me whole and happy again.” Well, he went off for the weekend and he came home and he had warmth in his eyes again. He was smiling and talkative. She asked what he’d learned about himself over the weekend, and he’d explained to her that he’d been feeling suffocated by their life recently, and that he wanted to engage in some threesomes to make him feel less encumbered. She considered this request with a straight face, like maybe you sometimes do what your marriage asks of you, even if you didn’t expect it. That was the worst part of this story, she said. That she was about to say yes to it. But then the husband said, “But not with you.”

  “What do you mean?” she’d asked.

  “I mean, I realize I want the sexual freedom that comes with multiple partners,” he’d said. “I want to explore my creative expression with other women. I think a lot of what I’m going through comes from having been so sexually repressed in my youth.” This was news to her. By her count, he was the opposite of sexually repressed. He wanted it five times a week at the minimum, and sometimes he wanted it kind of weird, and she had always complied. Maybe that was the problem? Maybe she should have made him want it more?

  “The life coach told you this was a good idea?” Ten thousand dollars.

  “She helped me realize it, yes.”

  “That threesomes would make yo
u feel better?”

  “Yes. It was a no-judgment zone.”

  She thought this was a phase at first, but he brought it up every fucking night and eventually she had to deal with the fact that her husband was asking not just to sleep with another woman, but to sleep with two other women, any woman but her, basically, and could she please occupy herself while he’s doing it. She finally asked for a divorce, her last particle of dignity rising up somehow, but her prenup was a prison; she only got something if he suggested the divorce, and he didn’t—no, he contested it! Can you imagine? He didn’t want to cheat on her, he’d said. He wanted to expand the marriage, was the word he used. “Yeah, to include everyone but me,” she’d said. She just couldn’t, she’d said. Her barely-hanging-on sense of self couldn’t allow her. He said it must mean that she didn’t love him that much. Now she looked at Toby. “You couldn’t possibly understand what it’s like to be owned by someone.” Toby took a long swallow of his Scotch.

  He watched her as she spoke. She used an aggressive concealer to cover up some periorbital shade beneath her eyes she wasn’t happy with, but she was tan, and the concealer was maybe purchased in a winter month; it had the effect of making her look as though she’d been on a tanning bed with large sunglasses. She had long black nails that ended in an actual point, like a spade. Her hands had large spots on them. He was pretty sure she was not forty-one.

  She moved the tiny straw around in her martini, looking down and then looking up at him while her head was still angled down. She was being flirtatious, and it occurred to him for the millionth time, but the first time on this date, that it was strange that they were making introductory talk when he had already seen her crotch. It was not that he was advocating for an immediate rush to bed. It was just that he thought it would make more sense, now that he’d seen her in her see-through underwear, to start in the middle somehow. Though maybe this—the stories and the confessions and the could you believe what he did to me—was the middle.

  Tess and her husband had gone to couples therapy. “Of course I was sure that when he heard himself talk about this, he’d realize how crazy he sounded. You would cause this much of a crisis in an eighteen-year marriage because of what? Because you wanted a threesome? With other people? I said to the therapist, ‘You think that’s normal? You think a man should just say he wants to cheat on his wife with not one woman, but with two other women? That his wife should be onboard with this?’ But who was paying the therapist? He was. And the therapist knew it.”

  She kept the cocktail straw as the bartender took her glass away, and ordered a second drink. She stuck the straw into the second glass and picked the toothpick out of it, and tried to scrape the olives along the side of the glass. They wouldn’t yield, so she had to take her knife-nails to them, using them to spear the olives and pull them off.

  Toby nodded in sympathy. “People sometimes change.”

  Tess looked up. “No, he didn’t really change. He was always into threesomes. That’s how we met.”

  “You met having a threesome with him?”

  “Yes. Graduate school. Late night. Me and my roommate. We all went out to breakfast the next morning. It was totally civilized. He had this other girlfriend at the time, and she came to the breakfast, too. My roommate and I could not get over that. But then he called me and told me he broke up with his girlfriend and wanted to see me again.” Tess shrugged and went back to her straw. “Who could have predicted this?”

  Was this how dating always was? Were there always this many stories? He didn’t remember the telling of stories, but maybe that was because back when he was young, nobody had stories yet; everything interesting was happening right then, not in the past. The stories he heard from divorced women were all the same—not the details, but the themes: This thing I thought was just a whim was actually an important part of my spouse’s identity, and still I’m surprised. This thing they had always been doing they kept doing and still I’m surprised. Here is how innocent I was and here is how cruel my spouse was.

  He wondered if he sounded like this from his parallax view. He wondered if there was a version of this story in which he was the villain. He wondered if Rachel was sitting in some ashram somewhere telling anyone who would listen what a victim she was. A victim. Yes, of a husband who put his own career aside and raised the children and gave them consistency—the children they’d both wanted! A husband who rooted for her at her every milestone of success. What could she possibly say about him? That he was “unambitious”? He was as ambitious as he was allowed to be. There isn’t room in one marriage for two people who are hogging all the oxygen. One of them has to answer the phone when the school calls. One of them has to know where the vaccine record is. One of them has to do the fucking dishes. It was entirely possible that the only version of a story like this you ever heard was from the aggrieved party, the one who made the sacrifices and thought that the sacrifice gave you one up on your spouse, but it didn’t. It only made the spouse feel more entitled to take. Trust me, Tess’s husband was somewhere right now, one woman sitting on his face while another sucked him off, and he was certainly not talking about the ways Tess let him down.

  “So,” she said. “What happened to you?”

  Later, at her apartment, when she was sitting atop his penis, bouncing up and down, her hands in her own hair like she was in a shampoo commercial, her head rolling around in what had to be exaggerated ecstasy—the sex was fine, but come on—he had the feeling that came up a full eighty percent of the time he’d been having sex with a new woman these days, which was that it didn’t quite matter to her that he was there. He was just a warm body. To imagine that the sex act was dependent on him was to miss what was going on here. The point was that the parade of women interested in intercourse with him was steady and strong. He was enjoying this. Did he even need to say that? He was enjoying this.

  * * *

  —

  HERE IS A mostly complete inventory of the women that Toby had encountered romantically, both sexually and otherwise, since he first moved out of his marital home and into the Ninety-fourth Street apartment where he sat on a beanbag chair he’d bought for Solly and first understood his phone’s new role in his life.

  His first date was with a divorced mother of three from Long Island, a setup that came from his cousin Cherry in Queens. Laurette was pretty and nice, nodding rhythmically and frowning as he explained who he was and what he did and what his life was like. After dinner he walked her through a park to her car and he got every signal in the world that it would be okay to kiss her: She was standing close, she was waiting, she wasn’t busying herself with keys or anything. And so he kissed her and for the first time since 1998, not even this century, not even this millennium, he put his lips on another woman and she kissed him back.

  Kissing another mouth, wow. He and Rachel had stopped kissing long ago. Even in the best of their times, Rachel was all business when it came to sex; she didn’t have time for extras. She barely had time for foreplay. This was different, and not just because it wasn’t sex. It was the strange feeling of taking ice skates off after wearing them for hours and walking on plain ground—you know how to do it but it’s different. Just wow. He and Laurette made out for five gooey minutes, Toby devouring her face, unaware of its corners and limits. Afterward, Toby skipped back to the train. Holy moly, he thought. You could opt out for fifteen years, and you could be beaten down to within an inch of personhood, but this was waiting on the other end, like a reward for all you had withstood.

  He and Laurette went on another date, and then another. On the third date, when dessert arrived, she leaned across the table at the steakhouse they were eating in and said, “You know, I’m looking to get married again, and you just got out. We are in very different places.” He wasn’t heartbroken, just surprised. He was surprised by the totally new-to-him notion that relationships didn’t all have to go anywhere; they didn’t ev
en have to be relationships. And here a revelation came to him, that he was under no real moral obligation to marry a woman he kissed. He felt like he might combust from the freedom he felt. All this new opportunity! There weren’t enough hours in the day!

  The first person he met on the app was Lisa, a thirty-six-year-old public school teacher in Harlem who led with how proud she was of her work—“Yes, it’s important, of course,” he kept saying—and defensive about the fact that she had never been married, which he hadn’t asked about. They had had dinner at an Italian place in the Village, because in the beginning it felt strange and disrespectful to be seen with another woman in his neighborhood, where he regularly bumped into his and Rachel’s friends and other parents from the school, and oh lord, Rachel and the children, too. Lisa asked Toby about his life, and he told her the truth, that he was confounded by his new situation, about how to manage all this with the kids, and she got angry and said, “I get it. You were married.” Toby went home after dinner without ordering dessert and masturbated.

  Keisha was a twenty-seven-year-old occupational therapist who strutted into the Murray Hill bar where they were meeting, ordered two Kamikazes, despite him saying, “Actually, no, I’m not really into—” and so drank both herself, then yelped a “Whoo!” and later, after four more drinks, wrapped her arm around his neck and a leg around his waist and told him to take her home. He couldn’t. “Come on, what’s wrong with this?” The this, she made clear, looking down, was her body on his, and he ached so badly for her but how could he? How could he take advantage of this young girl who was positively soaked in alcohol? He went home and masturbated, but he couldn’t come.

  Stacy was a thirty-eight-year-old dentist who wanted to make him dinner at her apartment. He said yes but then had to cancel because Rachel suddenly needed him to watch the kids. He texted a nice apology and went to pick up the kids and when next he saw his phone it was filled with eleven vicious texts back from Stacy, who apparently couldn’t believe she’d let herself trust another one of these assholes. You are human dirt, she texted him. Then she texted him a picture of her body in the mirror, just the neck down, and she was wearing an apron and fishnets and fluffy slipper heels and nothing else, and he was kind of relieved because that felt like maybe too much pressure for a first meeting.