Chapter 1: With Dates Like This Who Needs Hell?

"Well I'm giving up on love cause love's given up on me."

Kerosene by Miranda Lambert

"Check mate."

Caleb Rivers was not happy.

The twenty six year old man was currently sat Indian-style in the dimly lit living room of his best friend, Toby Cavanaugh. Directly in front of him was a chess board, its pieces illuminated by the glow of the fireplace. And to further kill any shred of dignity or general manhood he had; he was taking regular spoonfuls of rainbow colored ice-cream out of an oversized carton.

And he'd just lost the seventh consecutive freaking game of chess.

His main reason for being here was, of course, his fiancée. He had made the momentous mistake of involving the blond in his 'guy problems' and much to his dismay he'd been roped into "emotionally supporting" his best friend's "relationship blockade".

He'd tried to tell Hanna that male problems called for a lot less hugging and force feed ice cream and a lot more beer and national football. Men were just simpler like that. Which, obviously, led Hanna to misinterpreted everything he'd said ("So now you think I over complicate things?! Humph!") and earned him a spot on the sofa .

In his defense the couch had been with them since Hanna graduated fashion school a couple years back so it was lumpy and an awful shade of pink that had once been all the rage. So for those reasons he'd finally surrendered with his tail between his legs after three nights on that tiny sofa, and agreed to help Toby. Hanna's way.

But if you asked Caleb, Toby needed to get his act together and stop acting like such a whiny motherfu-

"Caleb. Are you even listening?"

Blue eyes stared back at him questioningly.

He blinked. "Of course I am! I came here to help you, man. And that I will do." He spooned some ice cream out of the carton." So tell me more about Sarah. Any potential?"

Toby let out a deep chuckle. "Actually her name was Susan..."

Caleb made a dismissive gesture. "Sarah, Susan, Savannah. It only really matters if she's second date material."

Toby shook his head.

"Coming from he who stalked his fiancée for three months before she even knew his name. While he knew everything from her birthdate to her social security number. Which you knew was wrong on so many different levels. I think getting her name right is minimalistic compared to you."

"I was a nineteen year old with an expensive laptop and way too much time on his hands." Caleb rolled his eyes. "Besides, the only thing wrong here is the fact that there's a Yankee game on and beers in your fridge but instead of watching it on your flat screen and drinking them we're talking about...feelings."

Toby shrugged and took a spoonful of ice cream."I already told you if you wanna watch it, be my guest."

Caleb sighed. "You know I can't. Hanna's a sniffer dog when it comes to honesty. It's like she has to smell the saturated sugar and lack of testosterone on me to know I was here."

Toby began dumping the chess pieces back into the box." I'm sure you're exaggerating."

Caleb pointed his spoon at the carpenter.

"I stopped by the store on my way home last week," he raised his eyebrows ," and they happen to be showing the Tigers game. I swear I only watch for two minutes. I get home and Dr Phyllis is asking me why I was watching the game on a TLT day."

"TLT?"

"Toby's Love Therapy."

"Are you serious? "

Caleb nodded."As a heart attack."

Caleb tossed his spoon on the rug, sick of the overly sweet flavour, and focused on his best friend.

" So, are you gonna go out with Susan again?"

Toby sighed. "I don't think so."

"Why not? She was perfect for you. Successful, attractive, smart, athletic even creative." Caleb shook his head."Hell. She owns a bespoke furniture shop."

"And?"

"And? Other than the fact no other chick in a three mile radius owns a bespoke furniture shop, they're all you've been talking about for three months." Caleb said. "Didn't you say you wanted CRD Construction & Design to branch out into customised furniture?"

"This was a date. Not a business meeting, Caleb. "

The moment Caleb and Toby had graduate from high school back in their home state of California, they'd left their home state with their stuff packed in Toby's truck, their life savings, and dreams of starting over again. As luck would have it they'd headed straight for the Big Apple where the twosome had made fast friends with a young man named Jason DiLaurentis, who took them under his wing and into his home. Turns out his grandmother had left him a large portion of her wealth and he'd had enough faith in the two to invest his inheritance in their small business plan and it'd been the beginning of a partnership unlike any other. They'd been a fast success with CRD Construction & Design with Toby and Jason focusing on the construction and designs while Caleb handled the technological side of the business. With their combined efforts they now own owned the third largest construction company in New York.

"Eh. Maybe your right. I mean you know what they say never mix business with pleasure."

Toby scoffed, standing to put the box and ice cream away. "Believe me, there was no pleasure at all. It might as well have been an interrogation. Except slightly more awkward with overpriced french food."

Caleb stood up from the floor and dumped himself unceremoniously onto Toby's couch. "Now you're exaggerating."

"Sadly," Toby moved into the kitchen area,"that's a pretty accurate description."

"Okay. So, Susan's a no go." Toby joined Caleb on the coach, handing the techy a beer. "Moving on. I hear Tracy Sweetman in Human Resources has the hots for you."

"Dating an employee? That may be some preteen fantasy but it's also highly inappropriate." Toby scoffed. "Besides, I don't think I can trust your matchmaking abilities anymore."

Caleb look thoroughly offended.

"I have no idea why you'd say that when it was me who set you up with Danni Carter last month. You guys had a connection."

"Yeah, until she got arrested on our fourth date."

"Oh come on! DUI is not that big of a deal. "

"It is when it's your fifth offence." Toby rolls his eyes. "Let's not forget Katie Reynolds. "

"How was I supposed to know she was an alcoholic?"

"Seriously. Do you just get these girls off the street?"

Caleb vigorously shook his head. "No. I met Katie when I picked Hanna up from yoga. But now that I think about it there is a AA group across the road..."

"Whatever." Toby said."And don't forget Karen. She arrived an hour late and thought my name was Ebenezer."

"Okay. I've messed up a few times."

Toby cocked an eyebrow. "A few times?"

Caleb nodded. "Yeah. A few times."

"Catherine Cunningham. Who laughed every two minutes. Yasmine Yardley. Had serious anger management issues. "

"Okay. But..."

"Emilia Jenkins. She could have won the prize of stereotypical Gold Digger of the century."

"But you've gotta admit..."

"Bethany Saldana. Who thought it was appropriate to bring her pet snake on a date. A snake! Or Chloe McCoy. Who was a synonym for bimbo."

"She loved nature... and Chloe's dad is the senator. "

"And there's no way we can forget about Fiona. Who told me all about her grandmother's colony issues over brunch."

Caleb waved his hands, signaling for Toby to shut up the hell up.

"Okay. You've made your point. I shouldn't quit my day job just yet."

Toby let out a dry humourless chuckle.

Caleb put his free hand on Toby's shoulder.

"I only do it 'cause I care Toby. I mean it's been a year since the Alison thing." Toby winced. He hated how even her name still affected him, that his wounds weren't yet healed," It's time to move on with someone else. Your twenty seven, its time to think about settling down...maybe starting a family. Three kids. Like you always wanted."

Toby took a drink of his beer. He'd almost had it all. The kids, marriage, and picket fence. With her. But now? Now, he wasn't even sure that was his dream anymore.

What was the point in settling down when it can all fall apart so easily?

"Maybe, I don't wanna settle down?" Toby said, more to himself than to Caleb." Maybe the single life was meant for me."

"You don't mean that."

"Don't I? I have you, and even Hanna, that I consider my family and any kids you are two have will always be in my life. What's the point in looking for someone else?"

Toby crossed one leg over the other and leaned back into the couch, ignoring Caleb's uneasy look.

"In fact. I don't need to date. I'm done with love all together."

Caleb looked disbelievingly at his best friend, then released a sorrowful groan followed swiftly by a face-palm.

Hanna was so gonna kill him.

Thoughts?