Chapter One – You don’t know Jack

To the reader,

A brief explanation;

I received a request last week. A simple request. During the week I had been in contact with a certain successful author who had found her success within the genre that I write. In the future she and I may work together with her helping me publish to a wider audience as well as assist with editing, creating new covers, and other aspects of promotion that I really don’t have a clue about. She had suggested that I revisit the “Breakup Man” story and expand it. She suggested a couple of tweaks and this is the first chapter of the result of those tweaks.

There will be 10-15 more chapters before this story comes to a conclusion. I’ll be doing my best to post one or more a week until then. It, like all of my writing, is a rough first draft, but if you like it be sure to let me know in the comments below.

So without further delay, here it is; “The Breakup Man – Revisited”




Chapter One – You don’t know Jack


“I suppose I should introduce myself.”

“It would seem appropriate–given the circumstances.”

Jack took a long drag on his cigarette and looked skyward before letting the smoke cascade out of his mouth easing the tension within his body. He crushed the cigarette into an ornate turtle shaped ashtray that sat on the small coffee table in front of him. He looked back up at her and sighed.

“Take your time. I’m here for you. If you want to share, or if you don’t, that’s your decision. You are in the driver’s seat.”

Jack smirked to himself. The driver’s seat is where he always seemed to find himself. Of course this woman was different than the others. She was his recently acquired therapist and judging by the décor of the office and the numerous diplomas adorning the wall behind her, she was going to be expensive. Jack took another deep breath and thought out what he was going to say before regaining eye contact with the middle aged better than average looking brunette in front of him. “I find myself at a crossroads.” he finally explained. “My–job, has become troubling lately. And–” he stopped for a moment and looked expectantly at the woman.

“You’re trying to decide if you’re willing to change.”


“Exactly.” Jack pointed at her and nodded. “The problem is that business–as it is, business is good. Really good. So it’s hard to let go of a good thing.”

“I see. If it’s a good thing, why are you questioning whether or not you want to continue?” she asked softly.

Jack nodded again before looking down and furrowing his brow. He rubbed his eyebrows frustratingly and looked back up at the brunette. “Look, these things, I’ve–I’ve never been to one of these things before. You know?”

“I understand.” she responded semi-robotically. “I’m the first therapist you’ve consulted with.”

“Yes.” he nodded, wincing as he did. He felt annoyed at his lack of confidence. It wasn’t a feeling he was used to.

“Well it’s perfectly natural to be trepidatious when meeting new people.”

“Not for me.”

“This is different though isn’t it.” she retorted, “You’ve come here with the specific intent of being vulnerable.”

Jack scrunched his face up and ran his hand across the thick short stubble on his face. He savoured the scratchiness against the skin of his hand. “Vulnerability isn’t my cup of tea.” he explained.

“Like I said before, you’re in charge here. We can talk as much or as little as you need to.” she responded in a soothing almost motherly tone.

Jack looked back up at her and decided it was time he explained to someone what he did for a living; how he got where he was; how he managed to drive to this appointment in a Maserati Grandtourismo; and how he managed to pay for his upscale condo. “Look, before we go on I need to make sure of something here.”


“This,” Jack pointed at himself then at his new therapist and again to himself, “All of this is confidential, correct?”


“So what I tell you, you can’t tell anyone?”


Jack took a long look at her, then looked back at the cigarette crushed in the ashtray. He felt the itch on his fingers to reach for another. “I get paid to seduce women.” he finally blurted, still looking at the ashtray and the small collection of ashes within.

The woman nodded thoughtfully as if this was something somehow normal. Her reaction was so stoic that Jack started to question whether or not she had heard him at all.

“Well, it’s more complicated than that actually.” he began to explain.

“You don’t have to explain yourself Jack. This is a safe place here. There are no judgements. I am here for you and you alone.” she said soothingly.

Jack sighed, and looked at her gratefully. The urge to reach for another smoke was clawing at his insides now but he pushed the anxious need away so that he could continue. “I have to explain because I need you to know what I’m going through. I need to–explain myself–to someone. I think.”

“I see.” she nodded and waited for him to continue.

“You see, it’s not the women who pay me, it’s their husbands.” Jack smirked a little without thinking.

“I see.” she nodded again, once more waiting on him to continue. The look on her face was still one of stoic resolve. She wasn’t scrunching her face up in disgusted. She hadn’t made any move to throw him out of her office. She simply sat and waited.

Jack looked back into her eyes and continued to explain how his profession, if he could call it that, really worked. “You see, I’m not a gigolo. I’m not a male prostitute or whatever. It’s–well it may actually be worse than that.” he paused and bit his lip in thought. “These women, they have husbands you see. Husbands that are usually very well off. Old money, new money, tech money, it doesn’t really matter except for perhaps the fact they’ve got it, and a lot of it.” Jack reached down and grabbed the ashtray, turning it and looking at it absent-mindedly. “Most of these guys married young, or married who they thought would be their one true love forever. Not one of them has a prenup and every one of them regrets that.” He placed the turtle ashtray back on the table and sat back up straight and proud as ever, “That–is where I come in.”

“I see.” she said softly, “Please, go on if you’d like to.”

Jack looked right at his therapist. His piercing blue grey eyes drilled into hers with a fierceness that was nearly predatory. “I’m their way out.” he explained. His tone had changed. Jack’s earlier discomfort had melted away and he continued to explain with an air of cocky pride “These guys pay me to seduce their wives so they can catch them cheating and fare better in the divorce settlement.” Jack raised his hands and shrugged, “It’s as simple and as complicated as that.”

His therapist nodded, “And this is how you make a living?” she asked more out of personal curiosity than professional duty.

“Oh yes.” Jack nodded, a boyish smirk crossing his face as he did. “These men, they pay well. All of them are under the impression that it would be difficult if not impossible to make their wives stray.” Jack shook his head and chuckled, “If they really knew how easy it was to get them to spend the night with me, I think they wouldn’t pay anywhere close to as much.”

“I see.” she nodded again. “So the pay is good. Is this why you do it?”

“Yes and no.” Jack shrugged. “Part of it is the challenge,” he admitted “seducing a married women is the sexual conquest equivalent as a big game hunter hunting a tiger.” He paused for a moment, “That sounds bad how I’m explaining it.”

“There are no judgements here, Jack.” she reiterated.

“I just mean, that the thrill is equivalent. I’m not trying to say that I’m hunting these women. That’s not who I am.”

“You don’t have to explain yourself to me Jack.”

“I feel like I do though. I’ve never actually explained this to anyone, ever. It’s–uncharted territory.”

“I see.” she repeated again, and nodded once more. Once again reverting back to her stoic gaze.

“So yes, the pay is good. Very good. It’s allowed me to live quite comfortably, and honestly with the money I’ve got now, and how I’ve done with investments I suppose in some ways I don’t even need to work anymore.”

“But you do.”


“Because of the thrill.”

Jack stopped and thought about it, then looked back at his therapist and nodded, “Yes, exactly. Because of the thrill. The–hunt, for a lack of a better explanation.”

“So the thrill is what keeps you coming back.”


“Even though you’re having moral questions about what you’re doing.”


“And so now you’re no longer sure if you can continue this profession?”

“Well I know I can do it, physically. That’s not the problem. The issue is that–” he frowned. “I don’t think I can handle it on a moral level anymore.”

“I see. So your issue is that your primary way of making money is breaking up marriages and though you may be good at it–”

“Very good at it,” Jack corrected.

“–though you may be very good at it.” she continued, “It’s hurting you on an emotional level.”

Jack nodded in agreement.

“So what is it that you want to do?” she asked, much to Jack’s disappointment.

“I thought that’s where you came in. I thought you would be able to help tell me what I should be doing.”

“Honestly Jack I’m your therapist, and I’m not here to make judgements or in this case career decisions for you. I’m just here to listen to you and perhaps help guide you to make your own decisions.”

Jack frowned and shook his head slightly irritated. “Well that’s not very much help.” he muttered.

“What I would ask you, Jack, is what do you think you should be doing next.”

“I don’t know.”

“If that was true you wouldn’t be here.” she pointed at Jack as he sat in front of her, “You’re here because you know you need to make a change, you’re just having trouble figuring out how you’re going to change.”

“I suppose you’re right.” Jack nodded thoughtfully. “It’s just,” he looked up at his doctor and smiled, “This–thing I’ve been doing. It’s–it’s not really who I am.”

“And who are you Jack?”

“I’m not the type of guy who hates on women and wants them to suffer.”

“I see.”

“But it seems that’s what I’m really good at.”

“But is it really Jack?” she asked softly. She reached out and placed her hand on the coffee table between the two of them. “Tell me again what it is that you do?”

“I break up marriages.”

“But how do you do that?”

“By seducing women into cheating on their husbands with me.”

“So what is it that you’re good at?”

Jack looked back up and smiled at his therapist shaking his head, “Fuck me.” he chuckled before holding his hand up, “Sorry, excuse my language. But fuck me. You’re right.”

She continued to look at him expressionless waiting on the next statement he was going to make.

“I’m not the one that breaks up these marriages, it’s the husbands who do that. I only seduce their wives. I seduce married women that have a substantial amount to lose if they’re caught. I’m not good at breaking up marriages, I’m good at giving women exactly what they’ve been missing in their lives.”

“So do you feel like that makes you a bad person?”

“No, not at all.” Jack smiled. “Jesus fuck. Why didn’t I see that?” he exclaimed in delight.

“Does that help you decide what you want to do with your situation then?”

“Yes; I think it does.” Jack smiled broadly.

“So what are you going to do then?” she asked, curious beyond professional limits.

“I’m going to keep doing the same thing,” he smirked “but it’s the women who will be my clients now, not the men.”

“What’s that?” the therapist couldn’t help but ask.

“The women–the women will be my clients from now on, not the husbands.”

“Oh, I see.” she responded, slightly baffled at this turn of events.

“Thanks Sarah, you’re the best.” Jack bubbled, leant over the coffee table and kissed her on her cheek. “I feel much better already.” he chuckled, standing and then turning towards the door.

“That’s–that’s good to hear.” she stood as well and followed him towards the exit. “Do I need to schedule any more appointments for you?” she asked cautiously.

“Sure, let’s try this again in a month and we’ll see how I’m doing.” Jack nodded before walking out of her office, down the hall, and out of sight.

Behind him, as he sauntered away Dr. Sarah Velenta bit her lip and turned back into her office hiding her disappointment that things had not turned out a little differently.



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