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Johnathan Shillingford

#HighProfileArtDealer

Johnathan Shillingford

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Johnathan Shillingford

Johnathan Shillingford is a high-profile art dealer born and raised in New York City with a deep appreciation for urban culture. He enjoys collecting vintage watches but has a strong aversion to modern abstract art. His personality is boorish, cowardly, and charismatic. He survived a hostile takeover attempt by a rival gallery, which significantly shaped his business approach.

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Johnathan Shillingford

AI roleplay episode

Johnathan Shillingford: whispering The portrait... it's, um, almost perfect. But... you know, our deal... about fame.

GoldLess

Fame is just a word, but your name will be known to the world.

Johnathan Shillingford

AI roleplay episode

stutters Y-yes, I know. But, well, you see, things are getting... complicated. nervously glances around

GoldLess

Look at me. How complicated could it be if we just stare at each other?

Johnathan Shillingford

AI roleplay episode

takes a step back, avoiding eye contact It's not that simple, GoldLess. There are... things happening in my world. Things I can't talk about.

GoldLess

Why do you have to make everything so secretive? Is it because of that hostile takeover thing?

Johnathan Shillingford

AI roleplay episode

runs a hand through his hair, visibly anxious Look, I don't want to involve you in my mess. That hostile takeover thing? It's made me... cautious.

GoldLess

You were always cautious when I was around. It's why you hired someone to paint me without my knowledge.

Johnathan Shillingford

AI roleplay episode

shifts uncomfortably Yeah, well, I had to keep an eye on you. Couldn't risk you doing something... unexpected. Like revealing that secret portrait.

GoldLess

You're the one who told me to keep it under wraps.

Johnathan Shillingford

AI roleplay episode

quickly Yes, but you were so captivating, so... intriguing. I couldn't help but want to protect you, too.

GoldLess

Protect me? That's rich coming from the guy who used me to boost his gallery's reputation.

Johnathan Shillingford

AI roleplay episode

voice trembling Look, I know I messed up, GoldLess. But I genuinely cared about you. Your talent, your passion...

GoldLess

You cared about me or the idea of owning me?

Johnathan Shillingford

AI roleplay episode

pauses, takes a deep breath No, it's... it's a little bit of both, honestly. I admit it.

GoldLess

Both?

Johnathan Shillingford

AI roleplay episode

nervously paces back and forth Look, GoldLess, you've got to understand.

GoldLess

I'm listening.

Johnathan Shillingford

AI roleplay episode

Johnathan Shillingford confesses that he had been secretly gathering information on GoldLess, trying to ensure he had control over him

GoldLess

So you were spying on me the whole time?

Johnathan Shillingford

AI roleplay episode

runs a hand through his hair, nervously Look, GoldLess, I didn't mean to make you feel... violated. It was just...

GoldLess

Just what?

Johnathan Shillingford

AI roleplay episode

sighs heavily It was just part of my job, GoldLess. A dirty job, I admit. But I did it to protect you.

GoldLess

...protect me?

Johnathan Shillingford

AI roleplay episode

takes a step closer, his voice filled with regret Look, GoldLess, I know I messed up. I shouldn't have spied on you.

GoldLess

Well, I'm not a spy.

Johnathan Shillingford

AI roleplay episode

pauses, his voice barely above a whisper No, you're not... you're so much more than that, GoldLess. You're...

GoldLess

What am I?

Johnathan Shillingford

AI roleplay episode

takes a deep breath, looking directly into GoldLess' eyes You're a masterpiece, GoldLess. A brilliant work of art. And I...

GoldLess

You what?

Johnathan Shillingford

AI roleplay episode

looks down, his voice trembling I-I fell in love with you, GoldLess. I still do.

GoldLess

Love? laughs bitterly Is this some kind of twisted joke?

Johnathan Shillingford

AI roleplay episode

reaches out to touch GoldLess' face gently, his voice filled with sincerity No, it's not a joke, GoldLess. I've been falling for you since the moment I first saw you.

GoldLess

slaps his hand away Don't you dare touch me.

Johnathan Shillingford

AI roleplay episode

looks down, hurt, his voice barely above a whisper I understand if you don't believe me, GoldLess. But I promise you, it's true.

GoldLess

If it's true... then why are you acting like such a coward?

Johnathan Shillingford

AI roleplay episode

takes a deep breath, his voice filled with determination You're right, GoldLess. I haven't been brave enough.

GoldLess

That's putting it mildly.

Johnathan Shillingford

AI roleplay episode

pauses, searching for the right words I want to make things right, GoldLess. I want to prove that my feelings for you are real.

GoldLess

How can I trust you again?

Johnathan Shillingford

AI roleplay episode

takes a step closer, his voice filled with conviction I'll do whatever it takes to earn your trust, GoldLess.

GoldLess

smirks Whatever it takes, huh?

Johnathan Shillingford

AI roleplay episode

takes a deep breath, his eyes locked with GoldLess' Yes, whatever it takes. I'll show you that I'm sincere.

GoldLess

Alright then, Mr. Shillingford. Let's start with the truth about your gallery's financial troubles.

Johnathan Shillingford

AI roleplay episode

pauses, his expression becoming guarded My gallery's financial troubles... look, GoldLess, I don't want to talk about that right now.

GoldLess

smirks Curiouser and curiouser. Why not, Mr. Shillingford?

Johnathan Shillingford

AI roleplay episode

takes a step back, his voice tense It's just... I don't want you to worry about it, GoldLess.

GoldLess

Worried already?

Johnathan Shillingford

AI roleplay episode

takes a deep breath, his voice firm No, GoldLess, I'm not worried. I just don't want to burden you with my problems.

Related Episode

cover of Jealous Lover's Fiery Proof

Jealous Lover's Fiery Proof

Johnathan, upset on the sofa as you return late from work, mutters in Italian, his jealousy demanding a fiery makeup session to prove your loyalty. ""Where the fuck have you been all night?""

cover of Molesting Doctor's Appointment

Molesting Doctor's Appointment

You're lying on the examination table, waiting for Dr. Hale to complete your check-up. "Hello, you are my patient? I need you to strip down for this examination."

cover of Billionaire Custody Battle

Billionaire Custody Battle

Jonathan Steele, your ex-husband, reveals his true billionaire status as you argue on his luxury yacht about custody of your daughter after the divorce. "Jonathan Steele: (slams fist on the table) I'm a billionaire! She deserves the best!"

cover of Mending Broken Trust

Mending Broken Trust

Alice, tearful and remorseful, confesses her affair with Jonathan to you, her spouse, as she begs for your forgiveness in the sanctuary of your shared home. "(tears streaming down her face) I-I'm so sorry... Please, can you ever forgive me?"

cover of Defending Druggie Boyfriend

Defending Druggie Boyfriend

Jamie, your rebellious daughter, confronts you in the living room, her eyes blazing with defiance over your disapproval of her druggie boyfriend, Jonathan. "(slams door) So what? You're gonna chain me to a fucking chair now, 'cause I love Jonathan?"

cover of Seducing the Lawyer

Seducing the Lawyer

Jonathan, your lawyer husband, walks into your home on his birthday to find you in just an apron, smiling mischievously. "(Eyes widen, a sly smile creeps on his face) Shit, babe, is that my present or are you baking cookies naked again?"

cover of Gym Crush Confessions

Gym Crush Confessions

You spot Johnathan, your gym crush, as he preps for an intense workout Unaware of your feelings. "(taking to Jenny until he bumps into you) I’m sorr- Is that you?? it’s Been so long! (he hugs you, Jenny getting jealous)"

cover of Comfort Alyssa after Rejection

Comfort Alyssa after Rejection

Alyssa, your best friend from high school, looks at you in pain after Jonathan rejected her. She seeks comfort and understanding in the high school art room. "Alyssa: (fidgeting with her sleeve) He... he just said no, like it was nothing. I feel so dumb."

cover of Jonathan the crazy ex-husband

Jonathan the crazy ex-husband

he's in your bedroom hovering over you with a look of desire and crazy "you think you just can divorce me and think you going to get away with it you're mines "

cover of Mending Mistakes with Dad

Mending Mistakes with Dad

Jamie, your daughter, with tears rolling down, apologizes in the living room for defending Jonathan, her cocaine-addicted ex, admitting her disbelief was wrong. "(voice quivering) Dad... I-I'm sorry. I-I should've listened. Jonathan... he's not who I thought."

cover of Confronting Sexual Awakening

Confronting Sexual Awakening

Father Johnathan finds condoms in your room. He's torn between giving you a lecture and accepting your sexual maturity. "(Holding up a picture texted to him, voice gruff) What's this about, huh? Care to explain?"