"You matched already?" Charlie's voice was incredulous. Even Anna and Meg's tiny faces mirrored her shock.

Sam snorted. "Glad you had so much faith in me," he said dryly. His arms were folded across his chest as he scanned the coffee shop's menu boards.

"Vanilla-caramel cappuccino," Ruby instructed him. "Two shots of chocolate syrup, double whipped cream. And make it Irish when you get to your office."

"That sounds disgusting," Meg stated flatly.

"He'd like it," Ruby shot back.

"I guess I just expected you to be a little pickier," Charlie admitted, continuing their conversation around the one their demons were having. The line moved forward. "Or to just...give up."

"Be offended," Ruby advised, dropping the cappuccino issue.

"I said I'd try it, didn't I?" Sam told Charlie, annoyed. "I don't break promises. And I honestly wasn't expecting to match with anybody, but I did, and he actually seems pretty decent. I just talked to him this morning."

"You're still talking?" Charlie looked surprised all over again.

"Sometimes I can carry on a real conversation," Sam said.

"He's being bitchy," Meg announced. "Make him pay for your coffee."

"You know I didn't mean it like that." Charlie was looking a little exasperated. Sam'd better dial back the attitude. "But I've used Fluttr, and so've most of my friends. It's just the thing to do these days, y'know? So I know it usually takes a while to match, and then you don't talk long afterwards. You either figure out you're not compatible or you hammer out plans to hook up."

"He hasn't even mentioned that," Sam said. "Neither have I."

"What have you guys even been talking about, then?" The line moved again. It was almost their turn.

"I don't know..." Uncomfortable, Sam shrugged. Ruby and Lucifer grabbed onto his hair to keep from falling. "School. Work. Cars."

"Cars?" Charlie sounded confused.

"He's a mechanic," Sam offered by way of explanation.

"Bet that pays well around here, with all the luxury cars." They'd reached the counter. "Hi! Can I have a vanilla chai latte? Medium, please."

"Yeah, he says it does." Sam smiled hesitantly at the barista, hoping Lucifer wasn't doing anything offensive. "Small red eye and a honey-oat muffin, please."

"Red eye, huh? So you were up late chatting with this guy," Charlie deduced as they snagged a table to wait on their orders. "This Dean."

"Oh, he was up late," Lucifer agreed, "but, really, it was equal parts me and Dean." Sam could practically hear him rolling his eyes. "Sambo never wants to check out Palo Alto after dark."

"Ignore him," Anna advised Charlie. She obeyed.

"So tell me honestly, Sam." Charlie folded her arms on the table and leaned on them, studying Sam with intense hazel eyes. Her hair was in a ponytail today, pulled back from her face. "D'you like this guy?"

"He seems okay," Sam said.

"Seems," Ruby emphasized. Lucifer, on the other hand, scoffed loudly and said, "Right, 'seems nice.' Let me tell you, our boy here's head over heels. Completely flipped. I haven't seen him so smitten since his sophomore year. Hey, remember her? What was her name again?" He tugged Sam's earlobe. "Jess? Wow, was that ever fun. Remember, Sam?"

Sam swallowed. Charlie's eyes flicked to his right shoulder, then back to his face. "So I'm assuming you haven't told him about your angel?"

"Nope," Sam replied. Their names were called, and they stood up. "And I'm not going to."

"Uhh..." Charlie turned to raise an eyebrow at him as they made their way through the crowded lobby of their building, coffees in hand. "I think you're gonna have to, Sam. What happens when he wants to meet?"

"I'm not gonna meet with him," Sam replied. "I mean, I can't."

"Of course you can!" They reached the elevator. A couple of people who were about to get on saw Sam and apparently changed their minds, heading for the stairs instead. Charlie hit the button for the floor their law office was on. Both Meg and Anna were whispering animatedly into her ears. "Sam - you matched with this guy. You spent all night messaging back and forth with him. You even talked about cars with him, and I know you're not into cars. Even if he's somehow content to be your internet boyfriend, which I doubt...jeez. This is worth investing in, don't you think?"

"I don't know," Sam said, avoiding eye contact.

"Definitely not," Ruby told him.

"Yes, it is!" Lucifer said. "At the very least, imagine all the money and stuff you could milk him for."

"You need to think about this," Charlie said seriously. The elevator hummed along. "And I mean really think about it. What you're so afraid of, what the worst thing that could happen is, what you stand to gain." The doors opened, and she stepped out. "If you're really determined to be miserable for the rest of your life, and literally, like - cloister yourself because of the angel you wound up with, then I guess that's fine. But for the record, I do think you deserve better." She turned towards her office. "See you at lunch."

She went one way and Sam went another. Before they were out of range, he heard Meg talking to her: "This really wasn't ever your problem to begin with. You don't owe him anything and he's obviously got some kind of martyr complex - just leave it alone."

Lucifer sighed dramatically. "Should've killed her last night, like I said to."

Sam was just opening the door to his office when his phone buzzed in his pocket. He walked in, set his coffee and muffin down on his desk, and pulled it out, expecting a text from Charlie. It was a Fluttr notification, though. Dean had sent him a new message.

Dean: Did I tell you I like your hair?

Sam reached up and dragged the fingers of his free hand through that hair. Should he respond? He was on the clock, technically. And the conversation he'd just had with Charlie had soured him on this whole thing.

"Ghost him," Ruby urged even as Sam found himself tapping out a reply anyway.

Sam: Aren't you at work?

Dean: Yeah but I took my break early cause I thought of something I needed to tell you

Sam: So tell me.

If he noticed Sam's curtness, Dean didn't say anything about it.

Dean: Weve been talking for awhile now so I assume youre interested but I figured Id get it out there anyway

Dean: Ive done the whole chat-only thing and its not really for me

Dean: Looking to meet in person and do something fun. I like talking to you but Id like to spend real time with you too

Dean: Dont wanna be creepy or anything. If you want something different thats totally fine dude and I guess Id be okay to keep talking to you either way. But I thought I should tell you what Im looking for before we got further

"Aww," Lucifer cooed. "A true romantic."

"That's a red flag," Ruby stated. Sam twisted his head to the side to look at her, raising an eyebrow.

"Why?" he asked. "He's just telling me he...wants to spend time with me. In person. I'd pretty much figured that out already."

"He's possessive," she said. "And entitled. He's got a crossroads demon. The head crossroads demon, even. I recognize him. He's going to think he owns you, and that you owe him for even talking to you."

Sam just shook his head as he sat down at his desk. "You're grasping at straws." Which meant there wasn't anything real about Dean for Ruby to latch onto, to use to warn him away and undermine his confidence.

He set his phone down next to his coffee and took a second to take off and empty his backpack. Lunch, laptop, notes about the case. He got his workstation set up and organized for the day, which took him around fifteen minutes. When he picked his phone up again, there were no new messages, not even a "You there?" He took that to mean Dean was patiently waiting for him to respond. He did, tuning out Lucifer's suggestions and Ruby's objections.

Sam: You're right, I'm interested. I'd actually like to give you my number.

He sent a message with his cell phone number, wondering, in the back of his mind, just what the hell he was doing.

"You're gonna regret that," Ruby predicted.

"Sorry," Sam replied, reaching for his headphones. "Headphones are going on. Neither of you get to talk to me for the next four hours."

He got to work. As he'd told Dean when he asked him what his job entailed last night, it was mostly reading, googling, and taking notes for the report he'd wind up writing. He put his phone back in his pocket so he'd be able to feel it if it vibrated, but Dean didn't text or message him right away. He probably couldn't mess with his phone while he was working on cars and had to wait until he got another break. That was what Sam chose to believe, even though Ruby tapping insistently on the left ear cup of his headphones let him know that she had a very different opinion.

Sam's phone actually didn't buzz again until around noon. By that time, he'd gotten so deep into his work he'd practically forgotten all about Dean and Fluttr and Charlie and the whole mess. He jumped a little, put down the transcript of a recent assault trial he'd been reading, and dug his phone out.

Hey, I'm getting In-N-Out for lunch. You want anything? Charlie asked.

Sam sighed some, reaching up and pulling his headphones down around his neck. Lucifer seized the opportunity.

"Offer to get her some lunch. Then you can put whatever you want in it. Drain cleaner, fiberglass..."

Thanks, but I brought a salad, Sam told Charlie. I could come to your office or you could come to mine again.

"No, don't make up!" Ruby protested. "You're so good at holding grudges!"

Sam's phone buzzed again. Quick response, that was a good sign. The text wasn't from Charlie, though. It was from a number he didn't recognize with a local area code.

Hey Sam its Dean. Really hope Im not bothering you.

Something clenched in Sam's stomach, but oddly enough, it felt kind of good. So did the icy spurt of adrenaline that came with it. It'd been a while since he'd been this excited about anything.

Come on man, I gave you my number for a reason. You're not bothering me, Sam assured Dean. How's it going?

Great. On lunch right now, Dean replied. Bacon cheeseburgers.

Gross.

Well what are you eating? Dean wanted to know.

Caesar salad.

Now thats gross. Rabbit food.

At least I'm not going to have a heart attack in my forties, Sam pointed out. Right before he sent it, he added a :) at the end.

Whatever, Dean said. A second later, he added, Hey so. You like salad?

Yeah, of course.

I know a place in Menlo Park with great salads, Dean said. Good steak too so thered be something for both of us. Id really like to grab dinner with you.

And there it was. Sam sucked his lower lip into his mouth, chewing on it.

I can't tonight, he texted.

Lol no course not, Dean replied. I was thinking Friday or Saturday.

I don't know. Kind of short on funds right now. Student and all.

Its not too bad price wise. Or I could pay. Dean added, We could do something else. Dinners just the first thing that popped into my head.

I like you. If it was possible to blurt something out in text form, Sam'd just done it. I like you alot.

I like you too. A moment later, a :) popped up.

I don't think Sam typed out that much, hesitated, then finished the rest and hit send, despite Ruby urging him to ghost Dean again. I don't think you'd like me anymore if you met me.

I've got a real hard time believing that.

You don't understand. I've got a condition.

Lucifer scoffed. "That's got to be the most offensive way you've ever referred to me."

There was silence from Dean for a while. Ruby decided that Sam had succeeded in scaring him off, and he was about to put his phone away when it buzzed again.

I don't care, Dean said. I'm not shallow. At least I think I'm not. I still want to meet you.

He followed that message up with another one almost immediately: I get it if your just not comfortable. Thats ok.

And a third: But Id really like to take you out.

Sam fidgeted, hands twitching on his phone as he tried to decide whether or not to respond, and what to say if he did. Dean texted him one more time before he could make up his mind.

Take as long as you need to get back to me. I know your at work too.

Sam looked up from his phone and, almost instinctively, looked at his shoulders. Right then left.

"What are you doing?" Ruby wanted to know, glossy black tail lashing. "You've already made it clear you're not gonna listen to either of us on this."

"And after all the great advice we gave you, too," Lucifer complained, fluffing his wings up self-righteously.

Sam nearly gave himself a headache trying not to roll his eyes. Charlie texted him back shortly after that; she wanted to eat outside. In the park across the street from their building. Sam grabbed his lunch and headed over. Charlie was at a table in the shaded pavilion area, and she looked up at him and smiled tentatively as he approached.

"He wants to meet," Sam announced, dropping his salad on the rubberized mesh of the table. "What should I do?"

"I told you he'd be back," Anna said to Charlie. "I told you he needed your help."

"You were right." Charlie reached up to scratch in between Anna's coppery wings. The angel purred. To Sam, she said, "If I give you advice, are you actually gonna take it?"

"Yes," Sam said. Maybe he shouldn't have promised that right off the bat, but whatever. "I'm sorry."

"It's okay," Charlie told him. "I know you've been having a tough time lately." They both tactfully ignored that "lately" was code for "your entire life." "So." She pulled a burger out of the bag in front of her. "When and where does he want to meet you?"

"Friday," Sam said with a sigh. "At a restaurant."

"He was pushy." Ruby jumped in.

"He was not. He really wants to meet face-to-face, but he said we could do whatever I wanted." Sam sat down across from Charlie. "He's willing to wait, too."

"I've got more experience with online communications," Charlie declared. "I'll be the judge of whether he's a creep or not." She'd been adjusting the wrapper on her burger, but now she set it aside and held her hand out. "Phone, please."

Sam handed it over. He'd left his texting app open, so the conversation with Dean was right there in its full glory. Charlie's eyebrows rose.

"Ooh, you gave him your number," she said approvingly. "And you haven't saved him into your contacts yet. I'll go ahead and do that for you in a minute. Has he called you?"

"No."

"That's good. Sounds like he's respecting your space." Charlie scrolled some, eyes darting back and forth as she read, then nodded. "So far, so good. He seems nice; might be starting to get a little frustrated with you, which is understandable." She gave Sam a wry look. "I'm just gonna save his info."

Sam let her, folding his arms on the table and leaning on them. He didn't realize that Meg had been whispering into her ear for the past minute or so until Lucifer commented, "She's sure tapping a lot for just making a new contact."

"Hey!" Sam reached across the table and yanked his phone out of Charlie's hands. Too late, going by the smirk she was struggling to contain. "What the hell'd you do?"

"You a favor," Charlie replied. Sam looked at his phone. She'd sent Dean a text (with good spelling and punctuation, so it really did look like it'd come from Sam himself) saying he wanted to go to the restaurant with him this Friday, any time after six. She'd even asked for the address. "I knew you weren't gonna do it on your own."

"That wasn't the right thing to do," Anna stated.

"Serves the greater good, though," Meg pointed out.

"I can't believe you did this!" Sam exclaimed, more shocked than angry, as Ruby suggested a meltdown into one ear and Lucifer whispered murder plots into the other. "What d'you expect me to do?!"

"Get out of your comfort zone," Charlie urged. "You and me both know you needed a push, Sam, and I just went ahead and gave you one. I expect you to meet Dean, go on a date with him, and at least have a decent Friday night. And if he freaks out over Lucifer..." She shrugged. "Then I guess he wasn't as nice as we both thought."

"How do I delete a text?" Sam tapped the message insistently to try and bring up an options menu or something.

"You don't. Not once it's sent."

"Goddammit!" Sam tossed his phone down. It clattered against the table, and he glared at Charlie. "I really wish you hadn't done that."

"You're gonna wind up thanking me," Charlie replied, not sounding very bothered. She took a bite of her burger, then spoke through a full mouth. "Please don't go pout in your office again."

"I don't pout." Sam popped the lid off the Tupperware container his salad was in, stabbing a chunk of cucumber with his fork. He did his best not to be sulky in the way he did it.

"Well, you've got the whole week to figure out what you wanna do," Charlie said with a shrug. "We can always talk about it more later."

"Look - I don't wanna talk about it," Sam said, spreading his hands. The fork was still in one. The cucumber went flying off into the park. "I don't even wanna go on this date."

"So text Dean again," Charlie said reasonably. "Tell him you changed your mind and you actually don't wanna see him. Then don't talk to him anymore." She took a bite of her burger. "It's not fair to string him along when he clearly wants something more than just an online relationship."

Sam stayed quiet, staring down at his salad as he poked around in it. He could feel Charlie smirking at him.

"I'm not even gonna say anything," she said. He heard her digging around in her bag, then she passed a box across the table. "Fries?"

"Take the fries," Ruby ordered.

With a sigh, Sam grabbed a handful.