Sam and Dean return home from a case, but are immediately called upon to investigate a puzzling mystery.  What is Jack hiding from Cas and the brothers?  Can the three men uncover Jack’s secret?

Three Men and a Valentine's Mystery


Dean walked into the library area of the bunker, plunking his duffel bag down on the table. "Hey, Cas," he said, greeting his Angel friend.

Cas looked up from the book he'd been reading. "Hello, Dean," he said pleasantly. "How did it go?"

"Good. Fine," Dean replied tersely. He stifled a yawn. "How are things here?"

"Quiet," Cas answered, closing the book.

"Hi, Cas, how's it going?" Sam came into the room, from down the hall. Unlike Dean, Sam usually took his travel bag to his room first, so that he could remove his dirty clothes for the laundry. "Where's Jack?" he asked, looking around.

"He's at the library," Cas advised.

"Uhhh...." Dean gestured to all the books on the shelves.

Cas shrugged. "He said he wanted to do some historical research," the Angel said. "I informed him that I could probably tell him anything he needed to know, but...."

Yeah, Sam thought. Literally. But he was puzzled now, too. "If that's the case, why didn't he just go on the computer?" he said, gesturing to Dean's laptop, which was sitting in its usual spot on the table. Sam had brought his own computer with them on the road, of course, but his brother had one, and it was right here.

"Plus, when's the last time a kid his age looked at an actual book?" Dean said pointedly.

"Wow. Do you ever sound like an old man, right now," Sam teased his brother. "Next, you'll be going outside and shaking your fist at the neighbours' kids, telling them to get off your lawn."

Dean made a face at Sam, but Cas was looking thoughtful now. Dean had made an excellent point. Actually, both of the Winchesters had. Why would Jack have needed to go to the library in town when he had everything he needed to do research right here, in the bunker? "I don't know," he mused aloud. Then his expression brightened. "Why don't the two of you rest, after your long trip? I'll drive to the library and get him."

Dean yawned again. "Sounds good to me. Hey, stop by the diner on your way back and pick up something for supper."

Cas smiled proudly. "There's no need to do that. Jack and I will cook dinner, while you both rest. We've been teaching ourselves how to do it, by watching videos online. It's amazing how many dishes there are available. If I was still a human, I would try a different one every day."

"Yeah, well, don't get too carried away," Dean said grumpily. "I want to eat something I can actually recognize."

"I know, Dean," Cas reassured his friend. "It'll be fine, I promise."

The elder Winchester eyed him suspiciously, but in the end, Dean's exhaustion from having driven most of the day won out. "OK, Cas. I'll be in my room. Call me when supper's ready."

"I think I'll go and lay down for a while, too," Sam said, nodding. A lot of times he dozed in the car, but that wasn't the same thing as sleeping in an actual bed, of course. Plus, he wanted to finish unpacking.

As the brothers moved down the hallway to their respective rooms, Dean pictured Cas and Jack in the kitchen, trying to learn how to cook by watching videos, and he shuddered a little. He made a mental note to check the batteries in the smoke detectors, once he was done napping. Better still, he'd get Sammy to do it. His brother wouldn't even need a stepladder. Oh, and he'd better check the medicine cabinet in the bathroom for some bicarb, while he was at it.

"See you in a couple of hours," Dean said to Sam as he reached the door to his room.



Despite all of Dean's worrying, dinner had turned out to be delicious. And once they'd had a good night's sleep afterwards, the brothers were relaxed and refreshed the next day.

"Let's get in the car and go somewhere," Sam said to the others. "I know: why don't we go for a hike? Get some fresh air, and exercise."

"Hike, schmike," Dean protested. "I just got plenty of fresh air and exercise, when we went into that forest to chase down those werewolves. I say we go to a matinee, and get big tubs of popcorn. With extra butter." He elbowed Jack. "You in?"

But surprisingly, Jack was shaking his head. "I can't," he said. "I have to go to the library."

"I thought we went over this, yesterday," Cas chided the young man gently. "There is no need to go to the library in town when you have everything you need, right here. Books, computers, and me. I was in existence for each and every major historical event. I remember being at the seashore one day when a little grey fish - "

"You already told me that story," Jack interrupted.

"Oh." Cas tried again. "Well, how about the real story behind The Flood? It didn't happen the way that most people think. You see, one day - "

Jack interrupted Cas again. He stood from his chair, shouldering his backpack. "I'm going to the library," he insisted.

"Jack," Cas said, and his voice was more stern this time.

Sam held up his hand. "Let me try, Cas." He flashed their Angel friend a brief grin. "But, put a pin in that Flood story, because I definitely want to hear about that, later." The younger Winchester faced Jack. "Look, I get it," Sam said earnestly. "I like libraries, too. Maybe if you could just tell us what you're researching, we could help you."

"No!" Jack said petulantly. "I want to go to the library. I HAVE to go to the library!" He looked at Dean. "Can I take one of the cars?"

Dean was staring at the young man incredulously. "No, you can't. You're not going anywhere until you tell us what this is all about."

"Fine. I'll take the bus, then," Jack fumed. He marched over to the stairs, took them two at a time, then closed the bunker door behind him with a bang.

Dean moved forward. "I'm gonna kick that kid's - "

Sam put a hand on his brother's arm, restraining him. "Let him go, Dean. If we go after him now, he's going to feel like we're ganging up on him." He sighed. "We all know there's something fishy going on here, but....it's the library we're talking about. He could be going someplace a lot worse. Right, Dean?"

"I have no idea what you're talking about," Dean said innocently, glancing at Cas to see if their friend was buying it. Cas's expression was dubious, so Dean shifted the focus back to Jack, where it belonged. "Are we sure he's really going to the library?" he asked the others.

"Oh, yes. He is. I picked him up there, yesterday," Cas confirmed.

They were all silent for a moment. Then Sam said, "I say we go there, and check it out."

The men were in agreement. There was no way they could just ignore Jack's strange behaviour. Dean grabbed the keys to the Impala. "Let's roll," he said decisively.



A short while later, Sam, Dean and Cas were peering out from the bookshelves in the Theology section, spying on Jack. Dean had suggested this particular section, saying no one ever went there. Cas had frowned, looking at his friend with a hurt expression. Dean wasn't necessarily wrong, the Angel admitted, but still....

"Shhh," Sam said to the other men, gesturing. His warning was fairly unnecessary, since they hadn't been making any noise. But it had served as a heads-up. Dean saw the person who was approaching the table where Jack was sitting, and he started to nod. Now it all made sense.

"She's cute," Dean remarked, as the young girl took a seat at the table opposite Jack. "I totally get it, now."

Sam was eyeing his brother. "Watch it, Dean. She's probably around 19, and you're, like, a hundred."

Dean was outraged. "Hey!" he protested.

"Well, to her you are, anyway," Sam pointed out.

"Shhhh!" Cas admonished the brothers. "They'll hear you!"

The men watched Jack and the girl interact. Jack was awkwardly shy when talking to the young lady, but she didn't seem to mind. The two of them talked softly for a while, and then the girl stood, picked up her backpack, and left.

Jack watched her exit the library, and then he raised his voice: "It's OK; you can come out, now."

The men emerged from their hiding place. "How did you know?" Cas asked the young man.

"I heard you," Jack told them. "I'm surprised the librarian didn't. I thought for sure she was going to tell you guys to keep it down. You weren't exactly being quiet."

"I TOLD you to be quiet, Cas," Dean said, smirking.

Cas ignored him. "Why didn't you just tell us, Jack?"

"I was embarrassed," Jack admitted. "I don't really know how to talk to girls."

"It looked like you were doing fine," Sam assured him.

"I want to ask her out, but...." Jack's voice trailed off for a second, and then he looked at the men. "Could you guys give me some advice on dating?"

"You have to bring her flowers," Cas said firmly. "And chocolates. What kind does she like? Do you know? Maybe you should bring several kinds of each, just to be sure. Maybe - "

"Don't worry about that junk," Dean interrupted his friend, shaking his head at Cas. "You don't need to do all that. Just....be cool."

"Cool?" Jack repeated, puzzled.

"Don't listen to him," Sam chimed in. "Just be interested in HER. What does she like? What does she want to do?"

"Yeah, and then you'll end up getting dragged to a chick flick," Dean scoffed. "If she really likes you, she wouldn't - " This time, Dean interrupted himself. Cas had moved away, and he was running his hands over the spines of some of the books at the end of the shelf in the next section over. "What are you doing?" Dean asked the Angel irritably.

"I'm looking for books on various types of flowers, and their significance," Cas said earnestly. "It's important that Jack send the right message with his choice."

Dean rolled his eyes, turning back to Jack. But now, Sam was weighing in again. "Don't listen to Dean," he repeated, thinking that should just be his go-to response for anything his brother said on this particular subject. "Most women like those kinds of movies," Sam said, starting to smile. "Hey, I just remembered: there's a small movie theatre uptown that shows older movies, and I'm pretty sure they're showing that one about the Titanic, this month. You know, for Valentine's Day. Maybe you should take her to see that."

"Bad idea, Sammy," Dean said, shaking his head vigorously. "Remember? Balthazar?"

"Oh. Yeah. Right," Sam said, looking thoughtful again.

"I don't know why he didn't like that song," Cas piped up. He was standing beside Dean now, leafing through a big book. "I liked it. I thought it was very romantic," Cas added.

"Yeah, well, you would," Dean said, rolling his eyes once more.

Cas was unperturbed. "I can't remember if white daffodils symbolize love, or a cure for baldness," he mused absently, turning another page in the book.

Sam and Dean were both staring at their Angel friend now. He had to be kidding with this. Cas looked up from the book. "What?" he asked them. "Why are you looking at me like that?"

After a moment, Sam said, "Tell you what, Jack. Let's all go for something to eat, and we'll talk about this some more. Deal?"

"Deal," Jack said, smiling. He grabbed his backpack.



Due to the mens' assistance, or more likely in spite of it, Jack had managed to get a date with his girl. They were going to a movie, the young man told them, and then probably for something to eat, afterwards. Jack had asked Dean if he could take one of the cars in the bunker's garage. He was a very safe driver, Jack had assured Dean. Castiel had taught him how to obey all of the rules of the road. Dean had fought to maintain a straight face. He was sure that was true. Cas drove like a little old lady, in Dean's opinion. Oh, well. At least he wouldn't have to worry about Jack speeding. In fact, he should probably tell the kid to leave earlier, if he wanted to make the previews.

Jack was in his room getting dressed now, and the men were hovering over him again. Dean had given Jack a thumbs-up on the T-shirt and jeans the young man was wearing, overruling Cas's suggestion that Jack should dress up a little more.

Sam was telling Jack he should shave before he put his shirt on, just in case. He peered closely at the young man's face. "DO you shave?" Sam quizzed him. "Do you know how?"

None of this was bothering Jack too much. He knew that they all cared about his happiness, and he appreciated that. But then, the men started to talk about the topic Jack had dreaded the most: the kiss goodnight, once the date was over.

"I don't think he should kiss her at all," Cas said, shaking his head. "That's much too forward, for a first date."

Dean stared at his friend. "What century are you living in? Of course he should kiss her," he insisted.

"Only kiss her if it feels right," Sam said to Jack, taking the reasonable approach. "She'll let you know if she wants you to kiss her."

"You mean she'll tell me so?" Jack inquired.

"Well, no, probably not. But, she'll send you a signal," Sam said, confusing the young man even more. "You'll know, Jack. You'll just know."

"I say you just go for it." Dean was still insistent. "Nothing ventured, nothing gained. No time like the present. A bird in the hand....OK, bad example. A bird in your hand would just poop in your hand. But, you get the idea."

"Now do you see why I always say not to listen to Dean?" Sam said, giving his brother an exasperated look.

"I don't even know why you're still talking about this," Cas admonished the brothers. "He's not going to kiss her. It's too soon."

"Stop!" Jack exclaimed suddenly. "Just....stop. I know you're only trying to help, but you're freaking me out, now! Can you all just leave me alone, for a few minutes? Please?"

The men fell silent. "We're sorry, Jack," Sam said softly. "You're right. We'll leave you alone, to get ready."

The trio filed out of the room as Jack stood there, motionless. Peace and quiet, at last. But then, he started to think about what all of them had said, and he got nervous again. Which was the right approach? If the men he looked up to the most couldn't even agree with each other, how was Jack supposed to know?

He went to his bed, opening up the laptop Dean had loaned him. "I can't do this," he muttered. "I have to cancel."

Cas had celestial hearing, so he heard what Jack had said. He moved forward as if to enter Jack's room, but Sam restrained him. The men hadn't gone far, of course. They were just outside, in the corridor.

"But - " Cas started to protest, and Dean shook his head. He was in agreement with his brother, for once. "Just wait," Dean said in a subdued voice. "We've got to let him handle this on his own."

Jack wasn't handling it, though. He was talking to the girl he was supposed to pick up in half an hour on the computer now, telling her he couldn't make it.

"I want to. I really do," the young man told her. "I just don't think I can."

"But you HAVE to!" she said fretfully. "You need to come! You HAVE to come!"

She was practically shouting now, so the men in the corridor couldn't help but overhear. Not that they'd been trying very hard not to, of course. The three of them exchanged worried glances. OK, this was getting weird. Why did she sound so upset?

"I know I do!" Jack agreed, raising his voice. He let out a frustrated breath. "OK, OK. I'll pick you up in twenty minutes." He closed the computer abruptly, and the three men were looking at each other, open-mouthed. What on earth was going on, here?



Sam, Dean and Cas sat in the very back row of the movie theatre, watching Jack and his date intently. So far, they hadn't seen anything alarming. The two young people looked like any other boy and girl out on a first date. But after that strange computer conversation, there was no way they were letting Jack out of their sight. They had waited until the couple were settled in their seats, and then the Winchesters and the Angel had crept quietly into the darkened theatre and taken their seats.

Dean groaned. It was a chick flick, one of those ones where the man and woman hate each others' guts, but then their paths keep crossing until, one day, they realize that they actually love each other. "Oh, come on," he groused. "There's no way that happens in real life."

The movie was finally ending now, with the obligatory scene where the couple confess that they'd really loved each other all along. It was unbelievable, Dean thought. "You wouldn't love her so much if you knew what she called you in the first ten minutes of the movie," he wisecracked, talking to the male lead.

There was a sniffling sound to Dean's right, and he turned his head slowly to look at Cas. "Are you crying?" Dean said incredulously.

"No," Cas said gruffly, quickly wiping the tears away with the back of his hand.

Sam was grinning. "Oh, well. It was kind of hokey, but I've seen worse," he remarked. "You could drive a truck through some of those plot holes, though. And there's no way that guy could afford a penthouse apartment in Manhattan; not on his salary."

"Yeah, well, you can write your review on NobodyCares .com later," Dean said, elbowing his brother, "but right now, we'd better get out of here, before they see us."

The men rose from their seats and headed outside. They stood indecisively in the parking lot.

"What should we do now?" Cas asked the others. "Should we follow them to the restaurant?"

"Maybe we're overreacting, here," Sam said. He was starting to feel more than a little silly about this whole thing. "They're entitled to their privacy, aren't they?"

Dean opened his mouth to say exactly what he thought Jack and the young girl were entitled to. But instead, he exclaimed, "Look out, Sammy! Behind you!"

But it was too late. A chubby, round-faced man wearing a too-small T-shirt and Bermuda shorts grabbed Sam around the waist, enveloping him in a big bear hug.

Dean reached for his weapon, but Cas put a hand on his friend's arm. "Stand down, Dean," the Angel said.

"I missed all of you so much," Cupid said earnestly, still hugging the stuffing out of Sam.

"Cupid, what are you doing here?" Cas asked the cherub, as Sam finally managed to extricate himself from the embrace.

"Ohhh," Dean said slowly. "I didn't recognize you with your clothes on. I mean....you know what I mean." He raised an eyebrow. "Shorts? In February? Really?"

"Hey, it beats what he wasn't wearing the last time we saw him," Sam quipped.

"C'mere, you," Cupid said as he opened his arms wide, advancing on Dean. The elder Winchester gave up, submitting to the embrace. Otherwise, Cupid would just chase him around until he did.

"I'll ask you again: what are you doing here, Cupid?" Cas said once more, this time with a bit of an edge to his voice.

"I thought that would be obvious, Castiel," Cupid replied, in a tone that was both sweet and slightly hurt, at the same time. He gave Dean one more bone-cracking squeeze and then mercifully released him. "It's Jack," Cupid went on. "I'm here on a divine mission. His father was an Archangel, and we need more Angels. It only makes sense. If we can teach him how to fall in love, he can help us to repopulate Heaven."

"There's only one problem with that," Dean commented. "Actually, there are a bunch of problems with that, but we'll stick to the main one, right now. Don't you get the news up there on Cloud Nine? Jack's out of juice. He doesn't have enough Heavenly mojo to fire up a light bulb. And he might not ever get it back."

Cupid's face fell for a moment, but then his expression brightened again. "Never say never," he said. "You've got to have faith. With real love, anything is possible."

Dean rolled his eyes. They'd said that in the movie he'd just been forced to watch, too. Cupid would have loved the stupid thing. Heck, he could've written it.

"Well, I don't think that this is the right way to go about repopulating Heaven," Cas told Cupid sternly. Then his tone softened somewhat. "But I do believe you're right about Jack. I think he might very well get his power back, some day. But, in the meantime, remove the spell from them."

"All right, Castiel," Cupid said glumly, waving his hand. "There. It's gone." But a moment later, his expression brightened again. "What about you, Castiel? It's about time you went out on a date, don't you think?" He snapped his fingers. "I know just the right lady for you, too. Leave it to me; I'll set it up."

"That's an excellent idea," Sam said, grinning. "You do that."

"No," Cas growled. But then he added, "Who is she?"

"Quick, Sammy, get your cell phone out and take a picture of Cas's face," Dean said, nudging his brother. "I didn't know Angels could blush."

"Great! Wonderful! Then, it's settled," Cupid said, wrapping his arms around Cas and hugging him tightly. "I'll be in touch." Then he vanished.

As Cas was recovering from Cupid's enthusiastic embrace, Jack came out of the theatre. "What are you guys doing here?" he asked them, perplexed.

Sam countered with, "Where's your date?"

"She went to the restroom," Jack answered him. "So, what ARE you doing here?" he repeated.

"Nothing. We were just leaving," Cas said hastily. But then, he paused. "Do you like her?" he asked Jack.

"Yeah," Jack said calmly, and Cas could tell with relief that Cupid's spell was indeed gone. "We're going for a burger and a milkshake, and then I'll take her home," Jack advised the men. "We won't be out late. She has school in the morning."

"Which burger place are you going to?" Dean asked the young man. "If it's the one on Main Street, if you mention my name, they'll give you extra pickles." Then he frowned. "But if it's the one on Elm, don't mention my name, especially if Fran still works there. It's a long story."

Sam eyed his brother suspiciously, shook his head, and then asked Jack, "What school does she go to? Where does she live?"

"Riverdale," Jack answered him. "That's the answer to both of your questions. Her name is Veronica. Veronica Lodge."

Cas and the Winchesters nodded with approval. Veronica Lodge, from Riverdale. A nice, normal girl, from a nice, normal place. Terrific. They had nothing to worry about.

"Enjoy the rest of your evening," Cas said to Jack, and the men headed to where the Impala was parked, to drive home.

Valentine Book

- THE END. -

What do you think?  Wouldn’t you love to see this story acted out by our guys?  I think it would be hilarious!

Is this how you would picture Jack’s first date? 
Who would be the ideal woman for Cas, and why? 
What really happened with Dean and Fran at that burger joint on Elm Street, anyway?

Please feel free to share your opinions and reactions in the Comments section!  Is there a situation you’d like to see our guys tackle in the future? Let me know!

If you liked this story, check out my other stories on the WFB Writers’ Page!  Happy Reading!”