~3rd Person POV~

"You know, you really lucked out with Jennie. Any normal day she'd never go for you!" Sam exclaimed, as Dean entered the kitchen. Dean sat down across from his brother and sighed.

"Yeah, she's really something, huh?" Dean asked, distantly.

"Yeah. We may or may not have sat and talked about your embarrassing childhood memories all afternoon. Plus I mean, she's letting us stay in her house and she even likes the same books as I do," Sam said.

"Hm," Dean sounded. "Yeah well I think I just screwed it up."

"What'd you do?" Sam asked, not surprised.

"There's this guy, he's kind of like her dad and she wants me to meet him at dinner tonight and I told her no," Dean replied.

"What? Why? You're crazy about this girl, Dean," Sam replied.

"So? Parents hate me! The minute I'd walk in the room, the guy would probably be banning her to see me ever again," Dean said, letting out another frustrated sigh.

"Dean, you've changed a lot. I don't think you should screw this up with her. I haven't seen you this happy in a long time... She could be really good for you, you know?" Sam advised.

"What would I even say to him? You're good with parents. Parents love you! Help me out, man," Dean begged. Sam laughed. "What this isn't funny!"

"Actually it's hilarious. Oh you have so much to learn. But you'll do it right? Just tell her that you've changed your mind and you'll go," Sam said.

"I don't know, this is kind of your forte," Dean said back.

"So you want me to go in place of you?" Sam asked.

"Are you using reverse psychology on me?" Dean asked back.

"No!" Sam replied, falsely defenseless.

"Mhm, sure," Dean replied. He sighed. Sam was right and he knew what he had to do. He was really starting to feel some strong feelings for Jennie and he wanted to be a part of her life and if this is what it took, then he was going to do it.

~End 3rd Person POV~

I stepped into the lively and alluring restaurant that was in an old lighthouse in Seattle.

"Table for Matthews," I said to the greeter at the door.

"Right this way," the woman said. I followed her to a table with three seats at it. Holden was already sitting there and he looked pleased to see me.

"Hi," I greeted, happily. I smoothed out my dress and sat down across from Holden.

"Where's the boyfriend?" Holden asked.

"Oh he couldn't make it," I replied.

"Oh," Holden sounded.

"No, not like that. He was really busy," I said.

"Right," Holden replied, unconvinced. I swallowed. I really couldn't defend Dean in this situation.

"Anyways, so how was the solo surgery?"

"Oh my God, it was amazing. It was almost like, like I was flying or something! It went really well too and right before I left I checked on the patient for post-op and he's doing fine," I said, happily. It was a definite switch from uncomfortable to a happy topic.

"I always knew, even when you were a scrawny ten year old running around my hospital that you'd be a surgeon some day," Holden replied.

I chuckled, "Yes, well it was you and my freakish fascination with the human heart that got me into it in the first place. I can't wait until I get to do cardiothoracic on my own though!"

"Woah there. Let's take it one step at a time," Holden laughed. I laughed with him.

"Your mom would drop you by the hospital and you'd sit there and do your math homework in the gallery of the OR while she'd go and teach. God, I can remember it like it was yesterday!" he exclaimed.

"It really does feel like just yesterday. Now I'm all grown up and I'm responsible for stuff," I said.

"You sure are all grown up. Your mother would be very proud of you, Jennie. I hope you know that. I know that things never worked out with her and I, but I really wish she could see you right now... everything you've done for yourself," Holden complimented.

"Thank you," I said back.

"Sorry, am I late?" a voice asked.

I turned around and I could barely believe the sight. Dean Winchester was standing behind me and he was nicely dressed for tonight. My heart rate sped up about a hundred times faster than it already was and a smile played upon my lips.

"No, you're just on time. Come sit," Holden said. He looked at me, smiling a little.

"Holden, this is, uh, this my, this is Dean," I introduced, reverting back to the fact that Dean and I hadn't even defined our relationship yet.

"I'm Holden. Holden Matthews. Well it's very nice to meet you, Mr…" Holden said, offering his hand out for Dean to shake.

"Winchester," Dean filled in, leaning over the table and taking Holden's hand, shaking it. He smiled respectively at Holden.

"Well it's very nice to meet you Mr. Winchester. You've got a nice firm handshake there!" Holden said, looking over at me and giving me a look as if to say 'you've got a real good one here'. I looked down and smiled to myself.

"How'd your solo surgery go?" Dean asked to me, kissing my cheek before sitting down in the empty chair at the table.

"Great. I'll tell you all about it later," I replied. I was still in shock and utter happiness that Dean had showed up.

"So I hear you've been playing the father to my girlfriend here," Dean said to Holden.

I looked up at Dean, bewildered. Had he just said girlfriend. He looked back at me and gave me a sweet smile. He nodded a little as if confirming what he had said. As if this night couldn't get any better...

"She's a handful, huh?" Holden asked, jokingly.

"Yeah she is. You know we first met in the ER. I needed stitches and she was actually disappointed that it wasn't anything life threatening or endangering," Dean informed.

"Oh God," I groaned, laughing a little.

"That sounds like my girl. I trained you well," Holden said.

"You're a surgeon too?" Dean asked.

"Retired. After a while you realize that you've been missing out on life so you decide to retire, take off and go to Europe while you still can!" Holden exclaimed.

"Europe? I've always wanted to go," Dean said.

"You should someday! You can even take Jennie here. She could use some time out of that damn OR," Holden said back.

"I can agree with that," Dean chuckled.

"Hey, I'm barely a resident! Cut me some slack! Taking off to Europe is in no way going to further my career," I protested.

Both Dean and Holden exchanged glances and then laughed. Wow, they were bonding quickly.

"Well, I think some time out of the OR won't kill you," Holden said back but then continued to tell Dean and I about his trip to Europe. "You see, I started off in London, yes? It was always so rainy though so then I went Amsterdam…"

I smiled. They were getting along. What was Dean talking about? He was great with parents. On top of the table, Dean reached for my hand and I took his. This was surreal, right here. I kept reminding myself that this was a moment I was never going to want to forget. Dinner went extremely well. Holden continued to talk about his travels around Europe and then asked Dean some questions. And Dean was fantastic!

"If you'd excuse me for a moment," Dean said, getting up from the table. "I've got to take this." Dean motioned to his cell phone before disappearing to the back of the restaurant.

"He really likes you, you know," Holden started.

"I do," I replied, happily.

"You look so happy, Jen. I haven't seen you like this since… well a very long time. Not this happy, at least. He's good for you," Holden said.

"So you like him?" I asked, hopefully.

"I do," Holden replied.

"Good. He was really worried that you wouldn't like him," I said.

"Is that why he wasn't going to show?" Holden asked.

"No, of course not," I lied.

Holden chuckled, "Jennie, you know you can't fool me with that. I too was a young man meeting my girlfriends' fathers too. It's an… intimidating thing and although I'm not your biological father, I'd like to think that you think of me as one."

I smiled, "Of course I do, Holden! You practically raised me."

"Oh, looks like he's back," Holden said, as Dean returned to the table.

"Did I miss anything?" Dean asked.

"No I was just heading out actually. You two enjoy the rest of your night. Jennie, I'll stop by the hospital tomorrow to say goodbye. My flight leaves at noon. And Dean, it was lovely meeting you. You'll take care of her, won't you?" Holden asked.

"You bet I will," Dean said back. "Nice meeting you too, sir." I smiled and the two shook hands. As soon as Holden left Dean and I had a moment to talk alone. We left the restaurant after paying and were just walking along the streets.

"So how'd I do?" Dean asked.

"You passed… with flying colors," I answered.

"Oh thank God," Dean sighed with relief.

"I don't know what you were talking about back there with your whole 'I'm not good with parents' thing. You were great with Holden. He loved you," I said.

"I don't know. I don't usually do that so I guess I've always just assumed from past experiences that I suck with parents," Dean replied, shrugging a little.

"What your experiences when you were like sixteen?" I asked.

"Exactly," he replied.

"It's a beautiful night," I admired, breathing in the cool autumn air and looking up at the stars.

"Jennie," Dean started.

"Yes?" I asked, returning my focus to him. The two of us were now standing, instead of walking.

"I meant what I said with Holden about you being my girlfriend," Dean said.

"Oh, yeah that," I said back.

"I mean, if you will be-," Dean started.

"Yes, I will," I replied.

He smiled and kissed me.

"But I have some bad news," Dean started, pulling away. Damn it.

"Oh?" I asked back.

"Yeah, my brother was on the phone and he found another case. We have to be in Phoenix by tomorrow so we're probably leaving tomorrow morning," Dean said.

"Oh," I replied, disappointedly.

"I'll be back in about a week," Dean reassured.

"Yeah, I know. I was just really starting to get used to having you around. You know, maybe you should break something so that you're admitted to the hospital for like a month," I joked.

He chuckled, "But then we'd have to go through that whole patient-doctor forbidden romance thing which was actually pretty hot."

I laughed, "Yeah but this time I'd be your girlfriend before your doctor. I'm kidding though. Please, don't break anything!"

"By the way, my brother really likes you," Dean added.

"Oh thank God! I was afraid he wouldn't but we bonded. We even like the same books," I said.

"Yeah he told me about that. If I didn't know better, I'd think the two of you were having a secret affair behind my back," Dean teased.

"Oh we are," I teased back.

The two of us laughed but I returned to my somewhat sad state of being. I didn't want him to leave and I was really trying not let this ruin my night.

"I'll be back in a week," Dean assured, giving my shoulder a tight squeeze.

I nodded, "You better be."

The two of us exchanged smiles and then kissed.