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English
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Published:
2020-06-05
Completed:
2020-06-05
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5,557
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3/3
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coulda, shoulda, woulda

Summary:

Prompt from LadyMaigrey: "Matt asking Karen out for the first date post-S3. It could have gone like this / It should have gone like this / But it actually happened like this."

Notes:

Thanks to LadyMaigrey for this excellent prompt! I think the point of it is to have one situation with three different endings, but I'm not that clever, so I just wrote three different takes and lightly linked them. Hope that's OK! (And I'm sorry this is such a fluff bomb!)

Many thanks to irelandhoneybee for cheerleading and tending to my anxiety. ❤️

Chapter 1: It could have gone like this…

Chapter Text

It all started when Karen put the coffee in front of him.

“What’s this for?” Matt asked, sitting up a bit straighter in his chair as she leaned over him to put the cup on his desk. “It smells amazing.” Or maybe that was the tantalizing waterfall of her hair brushing his arm.

“Just sharing the wealth,” she said, straightening back up. “There’s a new place down my way on Tenth.” Karen cleared her throat softly. “And no offense, but you look like you could use it.”

“Ouch.”

She laughed. “Not that bad. Just a little extra tired. Long night?”

He wet his lips. Right now would be around the time he usually gave a non-answer. But he was trying not to do that so much anymore. “I think it’s the weather. The criminals are heating up right along with the city — muggings, robberies, you name it.”

“Anything I can do to help?”

“Not anything more than you're already doing.”

“Well, hang in there,” she said, resting her hand on his shoulder and giving him a little squeeze. And, dammit, she was right on target — a particularly tense spot — and he couldn’t help the moaning sound that came out of his mouth.

Her breath caught. “You OK?”

“Yeah, yeah,” he said quickly. “I’m fine.”

“Would it help if I—?” She was already moving behind him, kneading her thumbs into the stiff muscles where his neck met his shoulders.

“Oh no, you don’t hav—” But his protests faded into breath at the sensation spreading through him. God, that felt good. His head dipped forward as she rubbed slow circles over him.

“Pressure OK?” she asked, her voice thready.

“Mmmhmm,” he sighed, not quite able to make words. He relaxed under her touch, letting her fingers work magic on him. It was so easy to let everything else fall away, to focus on the light skipping of her heartbeat and the heavy heat of her breathing.

It wasn’t a secret — at least not from him: She was as into this as he was.

For months now, they’d been moving closer, inch by painstaking inch, but the boundary line between friendship and romance still seemed uncrossable. Sometimes Matt thought he should just ask her out, but guilt and shame and regret always weighed down his tongue.

And there was something about asking her on a date, like they could put time back in the bottle, that felt wrong somehow. He didn’t really want to date Karen. He didn’t need to. Dates, the formal kind, like they had before, were for people who weren’t sure they wanted to be together. They were kind of like job interviews. And what he had in mind with Karen was something more akin to a corporate merger. A shared life.

But the thought of actually trying for that future terrified him. He was supposed to be moving beyond his fears, but none of that philosophical stuff seemed to matter when it came to Karen. If he screwed things up with her again, it would be—he didn’t even want to imagine it.

So he was waiting. If she said something, if she made a move, then he would reciprocate. Except that didn’t quite seem fair either, putting the burden on her. He was stuck.

Karen’s fingers dug in harder then, and Matt realized the weight of his thoughts had made him tense up. No more thinking. He was not going to miss out on this moment, whatever it meant.

The added pressure was good—really good, actually—and another noise escaped his throat when her thumb worked over a knot.

Karen inhaled sharply at the sound, then bit her lip, and damn that made him think way too much about her teeth and her tongue and the silky warmth of her mouth. Everything around them felt suspended — the minutes slowing down and pulling apart like taffy. The buzz of her touch was radiating from his scalp to his toes and if she didn’t stop soon, he was going to have an embarrassing problem for a morning in the office.

“Karen,” he said, almost a groan, and he brought his hands up over his shoulders to cover hers. He only meant to stop her, but the touch of skin on skin was electric. They froze, locked together.

And then Matt heard Foggy whistling down the hallway, and the spell was broken.

“Ah, thanks,” he said awkwardly, pulling away, and Karen made it over to her desk by the time Foggy opened the door.

“Hey, pals,” Foggy said, “what’s poppin’?”

Matt scooted his chair defensively under his desk and pretended to be very, very busy.

He pretended well enough that eventually he really did put the morning’s...distractions...out of his head. He was still typing away when Karen came back to the office after being out on a case for most of the day. Foggy was long gone. Karen didn’t interrupt Matt’s work, just packed up her things to go. But he couldn’t just let her leave. He had to say something.

He pulled out his earpiece as she passed his desk. “Hey,” he said.

“Hey,” she answered, a little breathlessly.

“I wanted to say thanks...for earlier,” he said. “I’ll have to return the favor sometime.”

“Sure.” She swallowed as her pulse accelerated. “But can I choose something better than a backrub?”

The broad wink in her tone left him speechless.

“Goodnight, Matt,” she said and flounced out of the office before he could choke out a response.

Jesus.

He knew a come-on when he heard one, having been on the receiving end of many over the years, but what the hell was he supposed to do with this one?

Did she really want—? Or was she just—? And how could he be certain?

It stayed on his mind all night — through an unmemorable dinner, through part of a podcast, through several rounds with the neighborhood’s thugs. They all went down more easily tonight. Maybe because he was more motivated.

Maybe because he knew where his feet would be carrying him when his work was done — or as done as it ever was.

He was just going to check in, he told himself. Make sure she was OK. He wasn’t going to bother her. She would definitely be sleeping.

Except she definitely wasn’t.

He knew he should turn around and go home. This was crazy. She was going to be totally creeped out.

But he was already tapping lightly on her window. She opened it right away. “I can’t believe it,” she said softly. “You’re here.”

“I probably shouldn’t be,” he said, the usual guilt and shame and regret flooding through him. “I’m sorry.”

“You know, Matt,” she said, “that gets really old.” And she reached out and tugged him through the window by his shirt. He went without complaint.

He barely had his boots on the floor before her hands were cupping his face and she was kissing him like she meant business.

“Should I—” he gasped out when they broke apart to breathe. “Should I ask you to dinner?”

“Why don’t we talk about it tomorrow?” she asked, kissing him again. “At breakfast.”