A/N: Takes place after The Surprise Party, 2x10. This will probably become moot after the next episode but oh well.
If he had wanted to, he could have slept with Ivy. She certainly had wanted to when she flashed that seductive smile at him, but instead he sat down and ordered a Scotch. Ivy was a little surprised by his actions, and although a good shag would have cleared his head, the guilt in the morning was not something he wanted to deal with.
He was trying to grow up he told himself. Turning 40, having a sexual harassment suit against him, and meeting Jimmy had made him realize he wasn't in his 20s anymore. He would still be the Dark Lord at work, but in his personal life, he no longer wished to be the big bad wolf.
Scotch in hand, he lifted the glass and toasted Ivy's birthday followed by a sizeable gulp of the liquid.
"So darling, how's your birthday been so far?" he asked the blonde.
"Well," she started. "Pretty amazing. Tom wrote me a song and had Liza Minnelli sing it!" she exclaimed.
"That is quite the birthday," he said while taking another sip of Scotch.
"Then I came here, had some cake, but unfortunately JFK had already left by then, so I guess you'll have to do," she teased by running her fingers through the hairs at the base of his neck.
"You wound me," he feigned hurt. "But I'm going to turn you down darling."
"Now I'm the wounded one," Ivy said as she removed her fingers.
"I'm trying to be an adult," he said while looking directly at her. "If I go home with you, I'd wake up feeling guilty."
"Guilty? Why would you feel that?" she asked with her voice raising an octave. "Did you feel guilty when you slept with me before? When you cheated on me? Are you seeing someone?"
"No, I didn't feel guilty when we were together. Yes, cheating on you made me feel guilty, and like a twat," he paused. He was definitely not in a relationship with Karen, no matter how much he wanted to be. She had made it clear that it wouldn't be happening soon. But that didn't mean he didn't want to be a better man. "I'm not in a relationship, but I want to be, so being with you would destroy any chance I have with her."
"Wow, the great Derek Wills chasing a woman. Don't they usually just throw themselves at you?" she asked with a trace amount of hurt lacing her voice. While she was over Derek, it always stung when your ex moved on.
"Not this one. She's too good for me, and is in a 'complicated relationship," he said using his fingers to add air quotes.
"When has that ever stopped you?" she asked. She knew him. When he wanted something, he usually got it at all costs.
"Never, but this time it's different," he said while drowning the rest of his drink. He went to signal the bartender for another when her hand stopped him.
"Whoever this person is, she's really got you tied up doesn't she?" Ivy asked with a little concern. Derek, even when dark and moody, was never like this.
"Yes, she does," he told her. This was an odd conversation to be having with his ex.
"I'm going to give some advice: don't give up, find a way," she said wistfully. Ivy was speaking from experience.
"I really hurt you, didn't I?" he asked.
"Yes," she answered with a far off look in her eyes.
"I'm really sorry," he said while he leaned over to give her a kiss on the cheek. He then stood, fished money from his pocket, and paid for his drink. "Thank you for the advice and happy birthday Ivy."
She stared after him, wondering who could have Derek Wills so turned around.
Ivy had been right of course. He was the Dark Lord, the taskmaster, the director that could make a rock bleed. So what made him give up like a little schoolboy when it came to Karen Cartwright? He surmised it was probably fear. He felt off balance when around her, but now, he was empowered by Ivy's advice. With his mind made up, he headed to Karen's apartment.
It was late, but the room lights were still on, and he could see someone move about, so he decided to buzz the apartment.
"Hello?" Ana answered the intercom.
"Ana, it's Derek, is Karen there?" he asked.
A momentary pause and then she answered. "No, she went out."
"Do you know when she'll be back?" he asked.
"Ummm...no. She might not be back tonight," Ana told him nervously. She really didn't want to become involved in this love triangle.
"She went out with Jimmy?" he guessed. He wouldn't give up, he repeated to himself.
"Yeahhh," Ana said, dragging out the word.
"It's okay," he answered. "I'll just see her tomorrow." Moving down the stairs he wasn't sure what his next move was. He wanted to stay and see her. But if she came home with, or went to that prick's home, it probably wouldn't do him any good to wait around. Checking his watch he noticed it was going on 2 AM. He weighed his options of finding them in a local place, or if he should just go home to fight this battle another day. Just as he made up his mind to walk away to grab a taxi, he saw them round the corner. They hadn't noticed him; they were too involved in their conversation. Well, he could turn tail and do this tomorrow, or he could the adult man he wanted to be. But the decision was made up for him when Jimmy looked up and spotted him.
"What are you doing here?" Jimmy spitted venomously at him.
"Derek..." Karen trailed off breathlessly. He could tell she was getting tired of this back and forth.
"I came to apologize," he said while pulling himself to his full height. His answer had seemed to placate Jimmy temporarily. He noticed Karen's eyes darting in between Jimmy and himself. She was trying to judge how this situation would play out. "And to ask if I could speak to Karen in private."
"I don't think..." Jimmy started to say before Karen cut in.
"He doesn't control my life, and neither do you," she pointed out. "Jimmy, go home. I'll see you tomorrow."
"I don't trust him," Derek heard Jimmy mumble into Karen's ear.
"But I do," Karen responded and patronizingly patted his arm. Jimmy appeared off-put, but kissed Karen's cheek and stalked off down the block.
"Derek, what is going on?" she asked, but he ignored her until Jimmy was firmly gone.
"I'm not going to stop," he said while holding her gaze firmly.
"What?" she asked with confusion her face.
"You never said yes or no. Just that you were in a relationship. I'm not going to stop," he reaffirmed.
"Derek, you can't pursue me," Karen tried to dissuade him.
"I'm retiring the big bad wolf routine. You make me want to be a better person, and I'm not going to stop," he repeated for the third time. "To prove it, after the opening weekend, I'll leave the show. That way it won't be about the director chasing the leading lady. It will be about Derek Wills chasing Karen Cartwright."
"Don't do that!" she protested. "Don't endanger everybody's dreams just because of some feelings."
"I won't. I'll make sure there is a good replacement," he countered her argument. "Stop being scared of me," he asked of her. He took a step closer and reached a hand out to her cheek. To Karen's credit, she didn't flinch. He lowered his face and purposely missed her mouth as his lips landed on her cheek for a quick peck before he retreated a few steps back.
"Goodnight Karen," he said while taking one last look at her face. She was flush but her eyes held no panic. "I'm not going to stop," he reminded her before turning around to make his way down the block.
For the first time in awhile, Derek knew what he wanted.