A/N: I got the funniest comment on this from Bookworms and Nerdity. It made me laugh out loud so I had to include it in the story. Hope you don't mind.

….

"Seriously? She ordered for you?" Ruby finished closing out the till and handed Emma her tips. It was Saturday night and she had just finished her shift at Skewer's.

"Yeah, she ordered this huge prime rib dinner for me," Emma was recounting her bizarre date with Regina as wiped down the tables in the small restaurant.

"Alex, come over here. You gotta hear this story. Okay, Emma, start over," Ruby waved over the busboy as the other servers sat around the bar folding napkins, airing wine and listening to the story of the date that went wrong.

"This client at the real estate firm asked me out after she closed on a big deal. It was awkward."

"She? Are you gay?" Alex asked as he took a seat, he hadn't considered it before, but after looking her over, he could see it.

"Sometimes," Emma said as an afterthought. "Anyway, she ordered my food for me, then she asked me to go to a ball and then…"

"She tried to feed her cake!" Ruby had already heard the story and was all too excited to provide the odder details. She picked up one of the forks she was polishing and made an eating motion.

"Where did she take you for dinner?" Alex asked, squinting in confusion. It was rather odd that someone who she had just met tried to feed her.

"The Chart House," Emma rolled her eyes as they all oohed and awed over the restaurant.

"She paid for all of this, right?"

"Yeah, I assume she did. I walked out on her," Emma continued with a shrug as she picked up a broom and swept pita crumbs from the floor.

"Who is this woman?" Ruby inquired, wondering where Emma found these types of people, and possibly where she could get herself a date with this sugar mama since Emma seemed to be done with her.

"Her name is Regina Mils. She's buying apartment complexes in the area. Apparently, she lives around here and has a lot of money to spend."

"No shit, Regina Mills? Be careful, Emma. I heard she killed her husband," Alex had lived in the area for a long time and knew all the gossip. "Her husband was Leo White: A super rich old guy. He was like the king of Melbourne, Florida."

"Are you sure? I heard he died of a heart attack in his sleep," Ruby added with skepticism. "Either way, did you search this Regina on Florida courts online?"

"No, you think I should?" Emma was feeling a bit worried at her friend's reactions to her story.

"I would. She knows where you work, and she has your number. She might be a serial killer. Like cut your heart out and eat it killer cray-cray. There are a lot of serial killers out of Florida."

"Okay, I know you just finished season 6 of Dexter on Netflix so don't even, but unfortunately, she knows where I live too," Emma shivered slightly as she finished sweeping up and wiped her hands on a towel.

"How does she know that? Finish the story, I know there's more," Alex leaned in closer to hear.

"So I left the restaurant and went out to my car and there was a freaking boot clamp thing on the front tire. I parked on the street. Okay, so there might have been a 'permit parking only' sign, but it was after business hours," Emma recounted, frustrated by the memory.

"OMG, she gave you a ride, huh?" Ruby clicked her tongue as the plot thickened.

"Yeah, she came up running behind me out of the restaurant and she looked super pissed off. She saw the boot and offered to take me home."

Emma was met with indignant stares, "What was I supposed to do? Walk? I live in Palm Bay."

"She seemed really upset when I got in her car, but she didn't apologize or anything. Suspiciously, she didn't have a boot on hers and she parked in a handicap spot."

"Wow, that's just downright evil," Alex added in judgment.

"She had weird crystals hanging from her rearview mirror and little voodoo doll things. It was kinda creepy," Emma admitted, thinking back on it. She never felt scared or in danger. Truthfully, she was simply offended by the woman's audacity.

"Did she try to put the moves on you?" Ruby leaned her chin on her hand in hope. "Do you have a picture of her? I have got see what this lady looks like."

"No, she didn't try anything, but she asked if I wanted to come home with her and have a drink. I declined," Emma was starting to get tired of talking about it. The story sounded almost embarrassing.

"So she dropped you off and you never have to see her again. I don't think it's that big of a deal. We've all had bad dates," one of the other waitresses, who had been listening in quietly piped up.

"It gets worse, Mary Margaret. When she dropped me off she gave me an envelope and told me not to look at it until I got inside," Emma ran her hand across her forehead as her cheeks turned red.

"What was in the envelope?" They all asked at once.

"Five hundred dollars!" Emma said in shame, covering her eyes. "I'm taking it back to her. I can't accept that cash. It's so wrong…"

"She honestly thinks you are a whore," Ruby lifted her hands to mouth in disbelief. "Google her now!"

"Yeah, a whore with no sex," Alex said with a shrug. "I've seen her before. She came in here for lunch one day. If she needs to hire an escort to get a date then there is no God."

"I think she felt bad about the boot on my car and that's why she gave me money. I don't know, but there's more…so the next morning, after I got my car unclamped and made it into work, my boss tells me that we'll be seeing a lot more of Regina Mills. Apparently, she was so impressed with our brokerage 'services' that she's bringing us all of her real estate business."

"Emma, you might want to change your name and move to Phoenix. That is seriously screwed up," Ruby pushed off the bar and started polishing silverware. "You should report her for harassment and solicitation."

"Though if she just wants to give you money…eh, I'm not really seeing the downside," Alex was ever so helpful, and he added in a conspiratorial tone, "If I were you, I would have let her feed me the cake."

"Yeah, I hardly think I've got a case against her. I agreed to go out to dinner with her. What am I supposed to tell the police? That she was creepy and tried to feed me cake?" Emma just wanted to let the whole thing go. "I don't hate her, but she did make me feel…trashy or beneath her. I don't know how to explain it."

Mary Margaret had pulled out her phone and was currently conducting an image search, "Wow, Emma is that her?" She flashed the screen to Emma and she confirmed it with a nod. The picture was a newspaper photo of Regina in a white tennis outfit, smiling brightly.

"I thought you said she was old?" Ruby grabbed the phone and studied the picture with approval. "Is she a member at Kiwi tennis club? That's where my Granny plays. I'm going to have to ask her about this Regina."

"I never said she was old…I said older. Like thirty or so…I'm not sure, and I didn't ask her," Emma looked at the picture and thought about Regina Mills. She had the distinct feeling that one way or another she was going to be seeing much more of the woman, and she wasn't sure that was entirely a bad thing.