jack/tony friendship: Debates
"Are you just going to stare at her until she files for sexual harassment or are you actually going to ask her out one day?"
Quietly Tony had stepped into Jack's office, finding him staring through his office window at Chloe's desk, the open report in his hands momentarily forgotten.
Jack coloured and got to his feet, muttering "I don't know what you're talking about."
"Cause you are" Tony protested with a smirk.
Jack defiantly crossed his arms in front of his chest.
"Come on, Jack. I'm talking about Chloe."
Jack tried to brush him off. "Anything else you want to discuss besides my dating plans? Otherwise I've work to do."
"Yeah. Maybe you'd get it done, too, if you finally asked her" Tony said, keeping his tone light to prevent Jack from taking offense.
Jack's eyes darted over Tony's shoulder for a second, searching Chloe's face. Then he sighed and turned back to his desk. Carefully setting down the manila folder he'd been holding he said:
"I don't know, Tony. I don't know if I'm ready."
Tony perched himself down on the edge of Jack's desk.
Softly he said: "Listen, I can't even try to understand how difficult this must be for you. But believe me, Jack, you are ready. And so you were when you met Kate."
Jack shook his head. "I wasn't. It was too early."
"This has nothing to do with you and Teri, no woman is ever going to replace her in your heart."
"It still feels like cheating on her" Jack said in a low voice, his eyes distant.
"It isn't, Jack. Don't deprive yourself of all happiness. It's not going to bring her back."
"I know" Jack said while his eyes moved to rest on the picture of Teri on his desk. "Yet I still wish it would."
"I know you do. And probably you will always do. But you deserve a second chance."
Jack's voice was raspy when he said: "Sometimes I'm not so sure about that."
"Don't go there. It wasn't your fault" Tony said emphatically.
"I should have..."
"You couldn't know."
"I..."
"Jack!" Tony had gotten up and had placed both his hands on Jack's shoulders causing him to look up at him.
"You did everything in your power" he said as calmly as he could.
Jack closed his eyes for a moment, taking a deep breath. Tony squeezed his best friend’s shoulder, taking his former seat once more.
"Thank you" Jack said when he opened his eyes.
Tony nodded. "You know, sometimes I think it might help you if you had someone to talk to."
"A shrink?" Jack asked, not too surprised.
Tony smiled "Actually I thought of a woman."
Jack rolled his eyes. "There we go."
"Come on, it would be good for you."
"Okay, let's assume for your entertainment that I'd agree. How do you think this would work? All I know about dating is from undercover-missions. I wouldn't want to test that on Chloe."
"So Chloe is it" Tony said with a grin.
Jack groaned in frustration when he realised he had given himself away.
"I knew it!" Tony said triumphantly.
"Try to remember that I'll shoot you if you tell her" Jack said.
"I won't. You will" Tony smirked mischievously.
"I most certainly won't. I don't know this stuff."
"It worked with Kate."
"It didn't. Kate and I just happened to be in the same wrong place at the wrong time."
"But you called her and asked her out."
"I didn't. She did." Jack looked almost comical in his desperation and Tony bit back a laugh.
"It's no big deal. Just ask her out. Might save you a lot of pacing"
"And what if she says no? It's going to be embarrassing."
"For a day maybe. But I bet she won't say no. I'd be flattered."
"Now that's a comfort now" Jack said sarcastically.
Tony grinned. "If I was a woman, that is."
"I actually got you meant it that way, believe it or not."
The phone rang and when Jack reached to answer it Tony got up as well.
"Bauer?"
In the door he turned back, mouthing an "Ask her!“ Grinning he dodged the pen Jack threw after him.

More please! :)
(And I seriously need to catch up on my fic reading!!!)
Thanks for your message- I am just about to go and reply :)