Summary: Emma has been trying to pick up the pieces of her life after her boyfriend Neal died. After a string of bad dates that she reluctantly goes on, she's either ready to re-examine her lifes choices or swear off men altogether. She meets Killian Jones in a...memorable way and what follows is a roller coaster ride of crazy. Will Emma rise to the challenge or buckle under the pressure of her ridiculously complicated life?

Rating: Eventual Mature Content

Notes: BIG HUGE Thank you to charmingturkeysandwich (tumblr), without her I can guarantee you this would not only not be posted, but would not have happened in the first place. She's an AMAZING friend and you should go follow her.

Chapter 1

Sitting in her living room, playing a drinking game with herself called "drink until he becomes tolerable" was not how Emma Swan saw her night going. This is what she gets for believing her friends when they say things like "Oh, Emma, he's so sweet, you'll just LOVE him" and "He seems a little weird but he's just so shy." Right. These guys are single for a reason. This is the conclusion she's reached at this point.

Because, really, having to deal with Weight Loss Fanatic, Baked Goods Guy, Sock Stealer, and now, Obsessive Quoter, she's heard the message from the universe loud and clear.

She is undateable.

She guesses she SHOULD be grateful that she's at least currently on a date with a decent human being. Because even though she's about 6 glasses of wine in and essentially a walking ad for "Don't do this ladies" he's being a decent guy and making sure she's hydrated, covered, and tucked in bed before letting himself out with a "Call me tomorrow if you want to get together, Emma. I had a really good time."

Of COURSE he did. Of course. Because she held her tongue when all she really wanted to say was "WOULD YOU PLEASE SHUT THE FUCK UP?!" Because, as Elsa said via text 'the characters are talking. Let them.'

Nope, she got a front row seat to the crazy 'I am going to obsessively quote V for Vendetta all night' show. Fuck. She hasn't even ever seen it! Now she doesn't want to.

This is why she doesn't date.

Her mother always says "Emma, you just have to let love in." Ok, Mom. Ok. Sure. Because that worked out so fantastic last time. Come ON.

Her mother was BIG on platitudes and general turns of phrase including, but not limited to:

Every cloud has a silver lining.
Look on the bright side.
If life gives you lemons...
We all have to do things we don't WANT to. (That one was a big one in her house)
If you do what you've always done, you'll get what you've always gotten
What doesn't kill you makes you stronger.

Her mother was a beautiful woman with a beautiful soul, and far too much optimism. Growing up (partially-but that's a whole other story) in their house was basically a walking, talking Disney commerical. Emma left at the age of 19 with stars in her eyes and a completely naive heart. That quickly changed. Thanks Neal!

Her parents are basically fairytale characters though, which is probably why she stayed with Neal for so long. Hoping (there's that damn word) that endurance and love would outlast any trial. Yeah, that worked really well. Right up until he died.

She wanted Henry to have what she had. Love. Support. Stability.

But, she couldn't give Henry the life she had. There was no way. She was 19 years old when he was born. Neal was 20. Sure, they should have had it together by those ages, at least partially, but they couldn't even pay rent on time.

As much as she loved her parents, and knew they'd move heaven and earth for her, she couldn't saddle them with herself, a newborn, and Neal.

They never knew the extent of Emma's struggles. She couldn't look them in the eyes, knowing everything they did for her, and tell them that they'd raised a failure.

Neal then took a liking to drugs and girls, and the general 'unhappiness' in life came shortly after. She worked 2 jobs to try and keep them afloat, but between having to pay for bills, daycare, and food- they just weren't making it. And with Neal not working, things just got to be more difficult.

She couldn't have a checking account because he'd written too many bad checks under their joint account. He got into her purse and took money when she was sleeping, so she couldn't keep the cash anywhere readily available, and whenever she'd try and get a savings account he'd find a way to charm the tellers into believing his stories about how she was 'too busy to make it to the bank' and couldn't they 'help him out just this once?' Always with their sweet Henry in tow. That's where Elsa came in. She doesn't know where she'd have been without her those couple of years it was really bad. Elsa put her money in a checking account under her name. Paid all the bills with it. And made sure they had food and whatever else they needed. She was likely supplementing Emma's income as much as she could without her being suspicious. She's never had the courage to ask her about it.

Just when they were getting their heads above water, she'd finally gotten a raise at her job doing sales for a small loan office. They were moving from their little apartment into a house with a yard, something she was really excited for because of the way Henry's eyes lit up when he saw it the first time. She was headed out to work when she got a phone call from Neal's friend Jeff. Neal stole the bowling tournament money. $650 she had to come up with by next Wednesday. She was livid. And sick of living this shit life. She deserved better, Henry deserved better.

Not only was he a cheating man whore who didn't want anything to do with her unless she was servicing his dick, he was a thieving drug addict who never lifted a finger to help raise their son. She was fed up with it all and picking up his slack.

All she ever wanted was what her parents had. That's what she reminded herself every time she'd ever taken him back. Henry didn't deserve the back and forth, he deserved to have his dad in his life, he deserved a two parent home.

Henry deserving a 'real father' resulted in her ignoring his many indiscretions at the sake of her own sanity, self esteem and heart.

Henry deserving to have his dad in his life resulted in her NOT asking him to pay bills when he didn't want to even though she was struggling.

Henry deserving a two parent home turned into her living a miserable life, crying in her bedroom every night because she had no clue where Neal was, who he was with, or if he even cared.

She wasn't stupid. When he told her he was just going to sleep in his car at work because he got out late and would just have to drive all the way back, she didn't believe him, really. She just didn't want to fight anymore. It hurt too much to realize that he thought so little about his family and so much about his dick. She just turned a blind eye to everything he was doing and hoped that it was a phase he'd soon grow out of.

The bowling money was what led to her snapping. It was the exact amount she needed for a security deposit on the house. Hell no. She wasn't going to live there any more. She could see the light at the end of the tunnel and she feared, honestly feared, that if she lost that light she'd lose herself much worse than she already had.

She dialed the phone, furious, ready to give Neal a piece of her mind.

Voicemail. Right. Like she expected anything else. That's ok. She'd waited this long, she could wait until he finally stumbled through the door.

Of course, that stumble through the door never came. Because, his fast and loose lifestyle finally caught up with him and he fell asleep while he was driving. Left of center, failed to negotiate a curve, hit a hollow tree, flipped his (her) car and wasn't wearing a seatbelt. Instant death.

So no one can really blame her for being an enemy of love, can they?

Which is why, at this moment, she's laying in her bed wondering what even is her life. Seriously. She has to go get Henry from her parents' house and she won't be able to deal with her Mother's chipper happiness and sunny disposition when she asks how the date went. It'll go like this "Sweetheart, how did your date go? Was he wonderful?" (Yes, she is that sickeningly optimistic) And then Emma will say "Have you ever drank so much just to pass out because having conversation was painful? It went like that." and an "Oh, Emma, your walls keep out pain, but they also keep out love." And she then realizes the internal conversation she's having with herself causes her to roll her eyes and that shit hurts. She's in for a long day.