One day, I sat down, with nothing in my hands. He raised an eyebrow, obviously curious. "No new homework today?"

I smiled. "Nope, today is something different. I have just one question: Who are your friends?" I paused. "Besides me, I mean."

His eyebrows furrowed. "Are we friends?"

"I can still announce to the world that you can't drink coffee."

"I mean, we're great friends!"

I laughed. "Better. Now answer the question."

"Easy." He shrugged his shoulders, "I don't have any."

"Why not."

"Men are intimidated by me."

I stared at him in shock. "I can't believe you can say that with a straight face. Groaning quietly, I rubbed my forehead. "I know I'm going to regret asking this, but... what about women?"

He made a face. "That's even worse, women are all the same. They're always throwing themselves at me."

"..."

After a long awkward pause, Jack finally noticed something was wrong. "Umm... Megan? Are you okay?"

I stood up, quietly muttering to myself. "Don't punch him. Don't punch him."

"Megan?"

"Stay here." I shot him a death glare, and he nodded up and down quickly, frozen in place.

I went around the café, talking quietly to a few people. Having found a few of my favorite regular customers, I brought them over with me to his table. Uncertain, Jack stared up at us with confusion.

"What's..."

"Jack, this is Clyde." I pointed at the first man, who looked to be in his seventies. "He is retired from the army. He likes dramas and is an avid sci-fi fan."

"Umm..." He tried to interject, but I ignored him.

"This is Jessica." I moved on to a young girl with bright blue hair who I guessed was in her early twenties. "She loves rock music and period romances."

"Megan..."

"And finally this is Francis." The middle-aged woman smiled and nodded as I called her name. "She used to box professionally and now raises three kids at home. She could defeat you on any video game console in any game. Trust me."

"What is..."

"Everyone, meet Jack." I gestured to the frozen, confused man still sitting down. "He's a socially inept, narcissistic jerk who think all men are intimidated by him and all women want to jump him."

Jack turned pale. "MEGAN!"

I continued. "But at heart he's not a bad guy, recently discovered a passion for dramatic stories in books and movies, and desperately needs friends." I turned back to them with a pleading expression. "Would you guys mind sitting down and spending some time with him?"

Francis laughed. "Sure thing, sweetie, anything for you." She sat down next to Jack with an interested expression.

"Hmmph, don't have anything better to do, I guess." Jessica glared at me for a moment but sat down as well with a sigh.

Now it was only Clyde. He had on a slightly lonely expression. "Are you sure I won't be a bother?"

At his question I smiled gently, patting him on the back. "It wouldn't be the same without you."

With that a broad grin spread across his face and he sat down cheerfully. I gave Jack a thumbs up, ignoring his panicked expression and left the group to get to know each other. My break was over anyways.

Not too surprisingly, as I had known they were all great people when I introduced them, they all got along pretty well. They met every morning for a few hours, talking and joking about a variety of different topics. A few of my other regulars sometimes joined in, and soon that group became even louder and more fun to watch. Honestly, they got along even better than I had hoped. Jack became less awkward over time, and I noticed that although he still paid attention to Darla from where she sat in her corner, it was no longer with that desperate, lonely atmosphere, as if his entire world centered around one person. He was hardly recognizable from the brooding intense person I had met before, who sat alone and stared at a girl for hours on end.

Not that there weren't some growing pains. We were still working on a few common sense things. Like the time Jessica's boyfriend dumped her, and I had to stop Jack from hiring an assassin to track him down. Or the time Clyde's credit card got denied, and so he bought the whole company and paid off his debt. Or when new smart phones showed up at Francis's house for all her kids. It was sweet, but a little over the top.

But still, the plan was going well...

Or so I thought.

"And that's when I pushed him out into the street, no pants and all!" Francis finished her slightly raunchy tale to the sound of all of us laughing. The ending caught me at just the wrong moment, and I choked on my coffee while laughing. Jack had to beat on my back with his hand while I tried to cough the hot beverage out of my trachea.

"You're gonna kill me with your stories one day, Francis." I wiped the tears from my eyes, still chuckling despite the sore throat.

Francis grinned. "I can't do that, Jack would never forgive me if I was the cause of him losing his precious girlfriend."

"..." Girlfriend?

I shook my head with a smile. "You got it all wrong. Jack and I are friends."

"Really?" Jessica raised an eyebrow

"Really." I answered firmly. "He's in love with someone else. I'm actually helping him out in romancing her."

The table was quiet, everyone wearing skeptical expressions. I turned to Jack, thinking hard.

"Which reminds me, I think it's time we move on to the next phase."

He sighed. "What's the next phase?"

"Actually talking to her." I smiled pulling him out of his chair. "Go, ask her about the book she's reading."

He glanced over, surprised. "I read that book last week."

"I know." I winked. "I wanted to make sure you were prepared." Pushing him towards her slightly, without giving him a chance to refuse, I sat down at the table with the group, preparing to watch the show.

"Do you really know what you are doing?" Clyde seemed a little upset, which I couldn't understand.

"Trust me, they're meant for each other. "

I chuckled quietly, watching as Jack sat down with Darla and started a conversation. It seemed natural and easy. I silently cheered for Jack in my mind, carefully staying quiet as to not break the atmosphere I saw building over there. And if there was a small burning sensation deep in my chest, I excused it as being a residual pain from accidentally breathing in my coffee instead of drinking it.

Clyde didn't seem convinced by my words. "If you say so..."

Slightly confused by the uncomfortable tension at our table, I excused myself and clocked back into work.

The next day when Darla came in to order her coffee, I stopped her for a moment, curious to know how Jack had done yesterday.

"So, I saw you and that young man were getting along pretty well yesterday." I grinned as I poured her coffee.

Her expression didn't change. "I guess."

Uh oh. Slightly disconcerted by her casual dismissal. I tried pushing harder. "I mean, it must be nice spending time with such a nice handsome guy, right?"

She took the coffee from me, looking slightly annoyed. "I mean, sure, if you like that kind of guy I guess.

My stomach dropped. "What kind of guy?"

"Nice, friendly... boring."

Boring? Before I could ask, she continued.

"I like dark, brooding mysterious guys better, you know..." she lifted the book in her hand as an example. "Like what you read in romance novels."

Oh no. "But... those kind of guys are one dimensional!"

"I want the kind of guy who would destroy someone for just looking at me wrong..."

"So a criminal."

"Who would buy an airplane and take me on a whirlwind trip around the world without notice."

"Wouldn't that be a little irresponsible?"

"Who is mysterious and secretive and doesn't get along with others well."

"I... I can't..." I held my head, which was now pounding and groaned. Not noticing my discomfort, Darla smiled, sipped her coffee and returned to her table. I crouched down on the floor, feeling terrible.

What had I done?

"Are you okay?" a familiar voice called out. I looked up to see Jack's concerned face leaning over the counter.

I felt so guilty; I could barely make eye contact. "Just reconsidering all my life choices."

"Okay..." he frowned, seeing me staying on the floor. "Can I help out? I'm kind of worried. You're not your normal weirdly overconfident and pushy self."

"I'll be fine." I waved a hand. "Just give me a minute and I'll make your drink."

"That's not important." He seemed almost ready to jump over the counter to check on me, so I stood up, forcing a smile.

"I'm okay, really. I just need to think through some things."

"If that's what you want... just know if you need to talk, I'm here." He grinned. "After all, you've been helping me out with all my life problems. The least I can do is return the favor."

I felt even worse. "Thanks."

That night I sat in my apartment. Thinking things through. I had been so focused on helping Jack become a well-rounded, adjusted person that I had forgotten that Darla had fallen for old, broody Jack in the book.

Had I ruined his chances at love?

Worried, I devised a new plan. I didn't want to tell Jack to return to how he used to be. If nothing else, he seemed a lot happier now. He had hobbies, friends and interests outside of work and love. He was a wonderful person and would make a great boyfriend.

I just needed to convince Darla of that.

I started operation: "Help Darla see the Light" the very next day.

My first actions were subtle, lending her some books I told her I thought she would enjoy. These were handpicked romance novels that showed healthy relationships and well rounded characters. Hopefully, I could slowly change her view on what romance meant. I also started dropping hints to her every day about how great Jack was, and despite myself, about how "mysterious" and "dark" I thought his background was. Honestly, I tried everything I could to help get her interested. I didn't see many results right away, but hopefully, if I persisted, I could slowly change her mind about her taste in men.

As for Jack...

Despite my lack of attention, he seemed to be doing just fine. I noticed that he still met with his group of coffee shop regulars, although the conversations seemed more serious and subdued these days. Even more disconcerting was the fact that as they were talking, they would frequently look over at me, and they always changed the subject whenever I got near.

Maybe they were giving him different advice on how to approach Darla and didn't want me to know?

After considering this, I decided not to interfere. After all, I hadn't been all that successful at helping his love life so far.

Not that I was completely out of the loop. Once, after a long conversation with the group, he approached me with a nervous expression.

"Hey Megan?"

I looked up, surprised. "Do you want a refill?" He normally only drank one cup.

"No, I just have a question." He fidgeted uncomfortably. "So if one were to get a girl that someone has... special feeling for, what should that person get?"

I laughed. "Why are you being so awkward, you want advice on what present to get Darla?"

"I didn't say that." He was frowning, and I couldn't help but laugh a little more.

"Okay, so the gift depends on who you are getting it for."

He thought it over. "Well, I want to really show her how much I care, so what about something big, like a new car, or a vacation home!"

I sighed. "Why do I even try?" I asked the heavens.

"What?"

"Big flashy presents like that when you two aren't even in a relationship is too weird. Plus, if you bought her a car or a home, she would have to pay the upkeep for it. It would end up being more of a burden than a present."

He seemed upset. "Then how do I express how much I care?"

"The thought means more than the actual present. Get her something she cares about, is interested in. That means you have spent time thinking about her and what she likes, and that time and consideration is really what conveys the most."

"Really?" He seemed unconvinced.

"Yeah."

"Thanks!" He walked away and rejoined the coffee group. They then put their heads together, talking seriously. I ignored the sidelong glances they sent my way, and refocused my efforts on trying to convince Darla that Jack was a great guy.

He must have appreciated my advice, however, as he brought by a thank you present a few days later, a book that I had been wanting to buy but was waiting for it to come out in trade paperback to be cheaper. I felt really grateful, touched that he had remembered that I liked that series. I was pretty sure I had only mentioned it offhandedly a few months back. It made me feel even worse that I had so far been unsuccessful at changing Darla's mind about Jack.