Chapter 20: Mr. Mayor

Shepard's habit of hitting the Red Rendevous every night after work hasn't changed after his baby daughter moved in.

"Hot wings again?" Anne tsks at his order "Those things will kill you, you know. Don't you ever eat a home cooked meal?"

Since the bar is dead as a tomb, Anne agrees to play some foosball with Shepard.

"I'd like to take you out sometime, Anne," Shepard says, "Somewhere nicer than this, where you aren't on the clock."

"I work here every night until 3 am," Anne answers.

"I'd really like to kiss you," Shepard says.

"Well, why don't you, then?"

And so he does. It's the sweetest kiss he's ever had. Before it's over, a few customers amble in, and Anne has to slip away from him and get back to her job.

Shepard's son Carter is born the next day, and once again it is Ewan who picks him up from the hospital.

Oregon becomes a toddler. With her mother's hair, she is clearly born to be a stylist.

Shepard is elected Local Representative, and he has his eyes on the upcoming mayoral election.

Allyson becomes an elder.

"Where did I get this horrible vest? I can't be seen wearing this!"

That's a bit better.

Ewan's turn follows.

"Did I say you could come behind my bar?" Anne asks the paparazzi, photographing Shepard as she makes him a Sweet Hijinks. Paparazzi are not known for their sense of propriety.

The Red Rendevous is hopping tonight; there won't be any dancing or games for Anne. The current mayor, Holly Greenwood, is here with Shepard tonight. She's vacating her seat and has been grooming him to be her successor. With the election so close, Shepard is glued to his phone, talking to his campaign manager. But despite the intense focus on his election, part of his mind is on Anne and how much he wants to get her alone and kiss her again.

That Friday night, Shepard throws a huge fundraiser for his campaign. His childhood friend Dennis Sargeant shows up. Though Shepard had used his influence in high school to get Chanel Knack-Racket to choose Dennis, Dennis ended up marrying Emilie Smith-Jones.

Probably not the most dignified way for the future mayor to greet his guests, but parties, even formal fundraisers, have that effect on Shepard. His campaign manager says it makes him more likeable, "You're the kind of guy people feel they could have a beer with. People like that in a leader."

Marina, the mother of his son, is here because she works for Shepard. These days she's proudly showing off her sparkly new wedding wing. She married Buddy Baker, a recent widower who inherited his wife Mary's entire fortune. Shepard is just grateful she had her eyes on a bigger prize than he represented; he couldn't imagine making his life with her.

Shepard is surprised to see Anne among his guests; she had told him she couldn't make it on account of her work.

He's thrilled to see her, of course, and heads right to her as soon as he notices her.

"Are you sure you want to be seen with me?" she asks as he takes her hand, "I'm not the kind of girl most people expect their mayor to be involved with. In public, at least."

"Anne, I'd like to be seen with you more often, all over town. We haven't even had the chance to go on a date, or had more than one kiss, but I would like nothing more than to acknowledge you as my girlfriend to the entire town."

Shepard was a little afraid she'd laugh at his declaration. Because he's only seen her in the bar where she works, and they'd only had that one kiss, he wasn't sure she felt the same way he did.

"You should kiss me after a speech like that," she says, and Shepard does as she asks. "I quit my job at the bar," she whispers in his ear, "I've made enough in tips that I can give it up and paint full time. And I'll be taking you up on that offer to go out somewhere nice." Shepard kisses her again, thrilled at the news. "You aren't raising any funds by spending all your time with me. Go do your political thing; we'll have plenty of time for dating tomorrow."

Shepard reluctantly pulls away from her, but she's right, he's here to raise funds for his campaign, not pursue his romance.

After a long evening of schmoozing and securing campaign donations, Shepard caught up to Anne by the buffet, having dinner with his mother. In that moment, he decides he's going to marry her someday.

Challenge Notes:

Dating a bartender NPC is next to impossible. The dive bar hours are 11am to 3am, 7 days a week. So for Shepard to pursue this, I had to move Anne into a house and change her job. I made her a self-employed painter. Now she'll be free all the time. (note to anyone who does this, even after I changed Anne's career, she was still assigned as mixologist. I had to go into edit town, go to the bar she worked in and delete the bar and replace it with a new one.)

Shepard actually did roll a wish to get married right at that moment when he was walking toward the buffet. Poor guy, you rolled single parent, it's not happening for you. Sorry.

Marina got married and is pregnant. Her husband Buddy will be turning elder in a few days, and has no kids with his first wife, who turned elder right after she married him. It's like he was a gold digger who got his older wife's fortune and now he's married a gold digger who'll take it from him.