This is another installment in our periodic editing program here at Writer Unboxed. The piece I’ve chosen for this particular exercise shows some real talent in description, setting, pacing, and dialogue, and it was enjoyable to read.
That said, it lacked dramatic focus, and too much of what was happening felt muddled or underdeveloped, so that the extended scene that comprises the piece had considerably less emotional impact than it could have. Much of what I say here will be focused on how we might improve that.
One of the difficulties in editing the piece was trying to discern the author’s intent given the muddled emotions and desire-line in the scene. This created constant uncertainty as to how to go about improving the piece. (It’s also one of the reasons this post is so long–sorry.)
Another difficulty resulted from not knowing from the outset whether it was intended as a short story (because its title, “Knowing When to Quit,” suggested a self-contained whole) or a chapter in a longer work. Given the number of references to incidents and characters outside the text itself—for example, the death of Eddie’s best friend, Nick, and the existence of the “Agency,” etc.—I decided that it was part of a larger work, and that the title was intended as a chapter title .
I’ll first present the text as edited. I have used bracketed numbers referencing my changes, and employed underlining where I have added text. My comments as to why I’ve made the changes will appear with those numbers for reference after the edited text. Then I’ll discuss in greater detail the more developmental aspects of what I would propose if I were the editor on this project.
Knowing When to Quit
The shiny spot on the bronze pig butt mounted above the entrance to The Brass Tail was tempting, but Josh preferred making his own luck.  The Marina district of San Francisco was eight miles and a world away from the sunlit streets of Sausalito. He’d left Kat there in the lengthening shadows, stubborn as ever in refusing his offer of help. Here, fog had reclaimed the streets, muffling traffic noises and sucking away the day’s warmth. 
Cold, damp, San Francisco fog air pooled around him Josh’s legs as he stood in the entry, taking . He stamped his feet and took a moment to absorb the energy of the room.  Despite her being eight miles away in sunlit Sausalito, Kat’s vibe saturated everything. She didn’t just own the place, she haunted it. 
Spotting an empty stool at the far  end of the bar, he threaded his way through a surprisingly lively Wednesday night crowd to claim a seat. He hadn’t completely shaken off the chill when Eddie appeared in front of him, exuding warmth filtered through a wary smile.
“Eating or drinking, son?” 
“Both.” Josh exhaled tension he hadn’t realized he was holding. “I was afraid Kat might have blackballed me.”
“Yeah, I heard that…Oh, never mind. Not my business.”
“What did she say?”
Eddie smiled as though to respond: Let’s not go there. “Nah. Look. She blows her stack, but she doesn’t hold a grudge. Besides, your money’s still good, right?”  Eddie’s smile brightened, and he He offered another strangely ambivalent smile as he slid a menu across the bar.  “We’ve got a single-barreled select Jack Daniels if you’re on expense account. Also some nice, very hoppy IPAs on tap.”
“Plain old Jack is fine. Make it a double, neat. Steak medium, hold the veggies, blue cheese on the salad. Butter AND and  sour cream on the potato. Pick me a nice red to go with.” He handed the menu back with a smile which Eddie did not return. Eddie’s welcome was genuine, and Kat’s vibe saturated the place. He remembered now why he’d never wanted to risk being exiled. 
The meal was delicious, and Eddie made sure his glass was never empty.  By 10 pm the bar was packed. Josh had a nice buzz going and a stack of bills in front of him from playing Liars Dice with a group of local singles.  He felt a twinge of guilt taking money from the two girls who were playing but shrugged it off as one of those outdated patriarchal instincts Kat kept telling him he had to lose. 
The lithe brunette next to him pressed her breasts against him again as she reached for the dice cup. He entertained a fleeting surge of desire, but he was still sober enough to recognize it was a bad idea to hook up with somebody else on Kat’s home turf.  Besides, he was here to talk to Eddie, not to get laid.  The breasts receded.
He’d been recruiting Kat for the Agency when she turned the tables and seduced him. Just thinking about that night in the stacks at the Borg, NYU’s Undergraduate library… He shifted on the barstool. Until that night, he hadn’t realized how good her mind-bending skills were. He suspected that even now she didn’t realize how good they were. And he wasn’t going to tell her, not unless she had a change of heart about working for the Agency. 
From this point on, I stopped doing line edits because it seemed to me that the piece would need significant rewriting, and correcting prose that in all likelihood will be significantly changed or even discarded seemed pointless.
Here came those breasts again. No mistaking the intent of the lovely…what was her name, Leela or Lilly? It didn’t matter, she was into him, not conversation. He knew he could simply lean over, kiss the back of her neck and make eye contact while he threw a hundred on the bar to clear his tab. That would be that. They might not even make it as far as his room.
He had his hand on his wallet when a chorus of “Josh, Josh, Josh” brought him around. He grabbed the dice cup. One more throw and then…He winked at the brunette, and she squeezed his leg. A rush of heat to his groin widened his grin. He glanced down at her hand, high up on his thigh. An icy rebuke jolted him, and he looked up, straight into Eddie’s implacable stare. He changed his plans.
It was after midnight before the bar crowd thinned out. The Liars Dice group moved on. Including the brunette–after writing her phone number on his wrist. He hadn’t meant to stay this late or drink this much, and he still needed to pick Eddie’s brain. He motioned Eddie over and pointed at the stack of bills.
“Lemme buy you a drink.”
Eddie set a second glass on the bar and poured Jack Daniels for both of them.
They clinked glasses and drank. Josh liked Eddie. Kat was lucky to have him, especially now that her father was gone. Josh hadn’t talked to Eddie since Nick’s death.
“Sorry about Nick.” Nick Beck had been Eddie’s best friend.
Eddie gave a stoic nod but his grief wordlessly filled the space between them. It was deep and permanent and cascaded over Josh’s carefully maintained boundaries, settling into the hole in Josh’s heart that Kat had carved when she walked out of his life. He no longer had the stomach to press Eddie for whatever secret Kat was keeping. He had a more important question.
“She’s fine.” Eddie’s clipped syllables did not invite further discussion, but Josh didn’t need an invitation.
“Sh-she happy?” Josh only needed a hint, a crumb of interest.
Eddie shrugged. “Most of the time.”
“Does she ever talk about…?”
Eddie’s obvious sympathy flushed Josh’s fledgling, drunken fantasy down the toilet. An unwelcome wave of sobriety washed over him, and his chin fell to his chest. He took a deep breath, lifted his head, and blinked to steady Eddie’s face.
“That calls for another drink.”
Eddie shook his head. “How about a cab instead?”
“Nah, I’m fine.”
“You happy?” Eddie was mocking him now. That was funny.
“Most of the time.” Josh deadpanned.
“Lotta fish in the sea…amirite?” Josh waved his glass in the general direction of the room and had to grab the bar to steady himself. “Kat was just the right size, though.” He raised his other hand to shoulder height, swaying for a moment and regretting that last drink.
“And smart. Not sweet. But kind. Yeah. She can be kind…unless she thinks you’re fuckin’ with her…she doesn’t like that. But if she’s not pissed at you…” He was rambling now, but Eddie was a great listener. Eddie would understand why Kat needed his help, even if–especially if–she didn’t want it. That was it. He’d almost forgotten why he was here. Eddie would help him convince Kat to tell him what she was hiding. He put his glass down and brought his elbows up onto the bar and leaned in. He just had to convince Eddie. But as he extended his hands and fingers, palms up to emphasize his point, he lost the thread. His hands continued to move on their own to cup an invisible form. “It’s…her ass. It’s perfect.”
Eddie wrapped an iron fist around his forearm. “That’s TMI, son. I’m calling you a cab.”
Josh flinched as the pressure registered. Chastened, he lowered his hands.
“Sorry. That wasn’t cool.” Josh regretted making Eddie uncomfortable, but he really needed another drink. He had reached that magical, alchemical degree of drunkenness where all things were possible. One more drink would keep him there long enough to drive back to Sausalito, to Kat. “One more. I’ll go.”
Eddie shook his head, but he walked over to the register and took a bill from the cash drawer. “Liars Poker, 9’s high. Your car key against one more drink.”
“You got it.” He fished his key out of his pocket and dropped it on the bar. He was totally going to cheat. Eddie was crazy if he thought he wouldn’t. He pointed to his head and then to Eddie’s, giving him fair warning. It wasn’t breaking the rules if you gave fair warning. He pulled a bill from his stack, magnanimous in victory, “You first.”
“What? You can’t start at 4 twos.” Josh reared back from the bar.
Eddie’s expression didn’t waver. Josh frowned at his own bill. He blinked, finding it hard to focus on the serial number. He had a two…maybe two of them. “Five twos.”
“Six,” Eddie said without hesitation.
Josh slapped his bill onto the bar. He couldn’t see the fucking numbers. “Challenge.”
Eddie stretched his bill out next to Josh’s. They both stared at them for a long second before Eddie swept Josh’s car key off the bar and into the cash drawer.
“Kat’s moved on, son. So should you.” Eddie said. “Your cab’s out front.”
 This is an intriguing first sentence, but it isn’t followed up in any meaningful way in the rest of the piece. Except for the games of Liar’s Dice, luck plays no part whatsoever in the ensuing action. This feels like a missed opportunity. The author might want to consider weaving the element of chance into the relationship between Josh & Kat—in particular, that he is going to test his luck tonight, hoping somehow to get back into Kat’s good graces. If something of that sort doesn’t happen, then this initial sentence just hangs there unsupported by what follows.
 These atmospherics and geographical details seem to relate back to a previous scene. Regardless, see how I blend them in, to the extent they’re necessary, at edit #4.
 Why does he stamp his feet? This suggests snow, not fog.
 Notice how I’ve moved things around to make better use of his moment at the door to assess the scene inside.
 Without further description, it’s impossible to know what distinguishes the “far” end of the bar from the “near” end, i.e., this is a meaningless descriptive. It’s also unnecessary—“the end of the bar” tells the reader all she needs to know.
 Later, Eddie uses “son” to refer to Josh, and that seems startling without this sort of introduction early on. How old is Eddie? What is the age difference between him and Josh? A brief physical description (beyond the smile) might be helpful as well.
 I’ve inserted some new dialogue and changed what was there for a couple of reasons. One, the depth and intensity of the relationship between Josh and Kat has to be at least suggested here. One of the chief shortcomings of the selection as it stands right now is there’s no way to genuinely appraise that relationship, what it really means to Josh, and why the breakup is so devastating—to the point of him denying it until Eddie makes it clear: It’s over. Two, Eddie’s behavior needs to remain consistent with “warm but wary.” Three, if all Kat did was “blow her stack,” it would seem that all that’s happened is that Josh and Kat have had a fight. But given how the story ends, that’s clearly not the case. As is, it sounds like Eddie is trying to reassure Josh that Kat just lost her temper and things will be fine, but why would he do that given what he knows? Instead, what he needs to say is something akin to: You’re still welcome here, even though…
 Why would Eddie’s smile brighten? See my notes elsewhere about the inconsistency of Eddie’s behavior and dialogue.
 Use italics not ALL CAPS for emphasis.
 Several things. First: “Eddie’s welcome was genuine.” We’re beyond the welcome, yes? (It’s covered by: Eddie appeared in front of him, etc.) Second, the “genuine” nature of the welcome is covered by the earlier “warmth,” but now the wariness has seemingly vanished. Why? Three, see where I moved mention of Kat’s vibe saturating the place (edit #4). And last: He remembered now why he’d never wanted to risk being exiled. Why “remembered”? How could he have forgotten?
 “Eddie made sure his glass was never empty.” Why? Eddie’s behavior is puzzling. He starts off by being wary, then his welcome is genuine, now he’s freely pouring alcohol. The whole payoff to this story is Eddie telling Josh that Kat has moved on and so should he. His behavior should conform to that. If he’s plying Josh with alcohol so he’s more susceptible to the brunette’s flirtation that should be clearer (i.e., since things are over with Kat, why not help Josh move on?). Also, is Josh there to get “a nice buzz going”? It seems he has a much different goal, yes?
 “with a group of local singles”. This is vague and confusing. The next sentence says he’s been playing with two young women. Stay with that. Narrow the focus, intensify the tension.
 “…one of those outdated patriarchal instincts Kat kept telling him he had to lose.” Another attempt to drop an intriguing clue that goes nowhere. Josh’s “patriarchal instincts” have no effect on what happens anywhere else in the selection. If this is going to be used, it should matter. Have him act “patriarchal” (sexist) with the brunette, for example.
 “he was still sober enough to recognize it was a bad idea to hook up with somebody else on Kat’s home turf.” Ya think? The fact the idea would even occur to him makes him out to be a bit on the dim side, if not a horny slob. This is another instance where Josh’s through-line—his pursuit of his objective—is muddled to the point of incomprehension.
 “Besides, he was here to talk to Eddie, not to get laid.” But Josh makes no real attempt to talk to Eddie. He SHOULD make that effort, but that needs to be shown in concrete action and developed.
 This paragraph suffers from two distinct faults. First, it presents a great deal of information that is never developed any further—or even addressed. (The Agency is never mentioned again.) Second, it creates ambiguity by making it unclear whether Josh’s real goal is to keep Kat as his lover or keep her as a recruit. If he himself is ambivalent, this should be addressed somehow in the scene—i.e., Eddie should point it out to him when they have that talk Josh supposedly came to have but which never materializes.
As noted in the excerpt, I stopped line editing at that point in the text, because it was becoming clear that the piece would have to be significantly rewritten.
First and foremost: there is simply too much muddle regarding why Josh is there, what he wants, and how he’s conducting himself. There seemed to be a confusion where an objective needed to be, and it’s hard to edit confidently when the underlying drama is so difficult to discern.
The piece involves three principle characters: Josh, Kat (who remains “offstage” throughout), and Eddie. Josh apparently intended to recruit Kat for “the Agency,” which is never made more clear. I’m guessing we’re supposed to assume it’s the CIA or a similar entity. Kat “turned the tables” on Josh and seduced him. They’ve had an affair, but it’s hit rocky terrain. Though neither the reader nor Josh knows it at the outset, Kat has moved on. The dramatic core of the scene is Josh’s still wanting Kat only to get this disturbing news and having to deal with it. It’s that simple. That simplicity would be commendable if it were used to create real drama.
Instead, Josh’s behavior resembles that of a sloppy drunk unsure of what he wants and barely able to control his impulses. This seems to be echoed by the title—i.e., Josh needs to learn when to stop both drinking and believing he has a shot at Kat. But that’s not a strong choice dramatically, and risks reader disinvestment with the character.
From what I can tell, Josh wants to learn from Eddie whether Kat is still interested in their relationship. That objective has to run through the story, and the stakes have to be meaningful and profound: He is here to make sure he hasn’t lost her.
I’d add that she’s the love of his life. (He may not know that, but the author should.) Right now, all of that is muddled. His desire through-line and the stakes are both unclear. That lack of clarity is compounded by both Josh’s and Eddie’s behavior, which is all over the map.
The first task in improving the story is to focus clearly on what Josh is trying to accomplish by coming to the restaurant/bar, and to raise the stakes: Josh is there to find out if Kat still wants to be with him, and that has to be extremely important to him. If the Agency plays any role in his desire to keep Kat in his life, that needs to play out much more openly, but I’d also make it secondary to his desire for her. He may try to mask his love with the professional consideration, but that needs to be clearer.
The second task is to recognize Eddie’s awareness of the breakup, and have him act accordingly. Right now it’s difficult to discern any core emotional truth to Eddie’s character, because his actions are contradictory. He’s wary but also more than happy to ply Josh with alcohol. He’s judgmental about Josh’s flirtation with the brunette even though he knows Kat is no longer interested. Own his core truth: His boss (Kat) has broken up with Josh, and Eddie has to walk the line between welcoming him to the bar but acknowledging the breakup.
Also, there needs to be a greater effort to embody Kat in the restaurant/bar. Since she’s physically absent, she needs to be made present through this setting. Josh needs to see her in its various inviting elements, and those elements have to be conveyed in some distinct way. Right now they’re merely suggested with the phrase, “Kat’s vibe saturated the place.” How? We need concrete details. And if that’s true, how could Josh allow himself to be seduced by the brunette?
Overall, too much is presented without follow-up, the emotional core of the scene feels confused, and the underlying drama is unrealized.
I would suggest having Josh clearly, even obsessively focused on speaking to Eddie about Kat. Show him making that effort. Josh wants to plead his case, use Eddie as his go-between. But the place is busy, Josh has to struggle to talk to Eddie, who is continually drawn away. As Josh continues to drink as he waits, his focus blurs, but does not dissolve. Meanwhile, the brunette makes a serious, committed play, and Josh has to fend her off without being rude (and thus causing a scene, which would undermine his status with Eddie and thus Kat). Make the brunette persistent, even obstinate—that will create tension, conflict, and drama (even humor, depending on how it’s played). Make Josh work to remain in Eddie’s (and thus Kat’s) good graces. (Maybe he even tells the brunette—“You do know I’m involved with the owner of this place, right?”—but she refuses to take the hint, places her hand on his thigh, writes her number on his wrist, etc.
Do that, and the final scene between the two men will have a real emotional payoff. Josh will have struggled all night to show he’s true to Kat, to prove his worth to Eddie, only to have Eddie give him the lowdown: Sorry, son. That ship has sailed.
The alternative: That Josh does not realize how much he wants Kat until Eddie gives that final lowdown (assuming this is what the author intends). If this is the case, then the extended scene needs to serve as a lesson, where action-by-action Josh is realizing how much he wants Kat (and not the brunette, etc.), regrets his drinking problem, makes a promise to get stronger on both fronts, only to realize at the end it’s too late.
What do you think? Do you agree with my suggestions and changes, or do you have a different take?