Later that evening Twilight, Rainbow Dash, Rarity, and Pinkie Pie headed for the hotel - an inexpensive one since they had no idea how long they'd be staying in Manehattan - while Applejack and Richie went out on their first official date. Applejack stopped by the hotel to get cleaned up first though, wanting to look at least decent since this was her first date ever. Rarity also insisted that she dress up for the occasion, but Applejack refused. They finally compromised by Rarity letting Applejack borrow one of her simpler ruby necklaces.

"That is a beautiful necklace." Richie smiled.

"Thanks, but it's actually Rarity's. She insisted that I look nice for our date." Applejack shrugged.

"Well even so it does look beautiful on you. But don't worry, I prefer your natural look to a dressed-up look." Richie said before opening the door to his family's carriage (Herbert was pulling it).

"Glad to hear that...an open-top carriage?" Applejack looked the carriage over, used to closed-top carriages in Manehattan.

"Oh it has a top, my parents and I just always preferred it down during clear days." Richie said. "We like watching the view."

"Heh, gotta admit I prefer watchin' it to participatin' in it." Applejack chuckled.

"Yeah, it can get crazy around here at times." Richie chuckled back. "But I got used to it. Even so I do prefer calm days to crazy ones, not that much of a city pony. Yeah there are plenty of things to do in a city, but there aren't that many places to play."

"I hear ya." Applejack agreed.

They continued talking a bit until they reached the theater where The Sleepy Chaperone was playing.

"I'll meet you two back here after the play, going to do a bit of shopping." Herbert said. "I want to make sure there'll be plenty of food for Gloria, Omar, and the orphans for a while."

"All right, see you later Herbert." Richie smiled.

"Bye Herbert." Applejack waved as Herbert trotted off.

They then went inside and Applejack enjoyed the play from the beginning. The set-up was really cool, it first opened in a stallion's apartment. The stallion greeted the audience and explained that he was feeling blue and so decided to play one of his records, which happened to be The Sleepy Chaperone. Then as the musical part started the stallion's apartment altered itself to resemble the lobby of a mansion. Said mansion belonged to an absent-minded mare who was hosting the wedding. The other characters entered singing their own introductions, including two gangsters who were posing as bakery chefs. There was even a pegasus who flew other ponies from one place to another for a living.

Sure enough Richie was right, the musical was definitely a comedy. Applejack laughed along with Richie for at least half of the play, enjoyed the music, and loved how the groom obviously loved his bride for herself instead of for being a famous and attractive actress.

After the musical they went straight to dinner, this time a restaurant that was slightly fancier than the last one they went to yet still served good portions.

"I'll be right back, I have to use the little colt's room." Richie said before leaving.

"No prob." Applejack smiled as she slid into the booth they were going to eat at.

However they weren't alone, a pony Applejack didn't expect to see soon entered the restaurant. Trenderhoof. He instantly spotted Applejack and went over to her.

"Applejack? Fancy meeting you here." Trenderhoof smiled.

On the outside Applejack tried not to look annoyed, but on the inside she groaned. Before tonight she hoped she would never have to deal with his flirting ever again.

"Yeah, fancy that." She deadpanned.

"It must be fate, us meeting in the same restaurant in Manehattan of all places. Listen I still really like you and would like to get to know you more. May I join you?" Trenderhoof lifted Applejack's hoof as if he was going to kiss it.

"Mr. Trenderhoof? Well hi there, I recognize you from your articles." Richie smiled, having just returned.

Applejack said a prayer of relief in her mind.

"Well Mr. Richie Fillyanthropy. I'm glad you showed up, I came here looking for an interview." Trenderhoof smiled. "I heard about your generous act of turning your home into the new orphanage and want to do an article on it."

"Sure thing, but it'll have to wait until tomorrow. I'm on a date right now." Richie said before getting into the seat opposite Applejack's.

Trenderhoof's smile turned into a look of shock.

"Oh...you two are dating?" He said.

"Yeah, we met in Ponyville when my uncle had me banished from Manehattan and she and her friends helped me clear my name." Richie smiled. "I fell in love with her about three days ago and she returned my feelings today."

"Eeyup." Applejack smiled at Richie lovingly, partly because she really did love him and partly because she hoped it would help get Trenderhoof to finally leave her alone.

Richie blushed at the way she was looking at him, and couldn't help but smile lovingly back at her.

"I see...I'll leave you two alone now...I'm kinda hungry anyway." Trenderhoof said awkwardly and disappointedly before going to find an empty table.

"Hope we didn't embarrass him." Richie said sympathetically. "It can't be easy losing the mare you like."

"I'm sure he'll get over it, he only had a crush on me. Besides, no one was really looking at us." Applejack pointed out.

"True."

They then ordered dinner and switched the conversation to more pleasant topics. After dinner they left to walk back to the hotel, since the restaurant was close enough to it for that.

"Um, hello again." Trenderhoof caught up to them awkwardly. "Sorry to intrude on your date like this, but I can't help wondering: Mr. Fillyanthropy, how did you win Applejack over?"

"Look, Trenderhoof, originally I just wasn't into datin' in general because I'm a workin' mare and put my family first." Applejack said. "But after I met Richie, well, I couldn't help but fall in love with him. You see, yer simply not my type and he is. I need somepony who has a strong love of family, who's willin' to work hard at what they do for a livin', and who's willing to help others no matter the cost. Plus, to be frank, somepony humble. And that's Richie."

"Ah...I get it." Trenderhoof was still disappointed, but he wasn't going to be a sore loser. "I accept my loss. Congratulations Mr. Fillyanthropy, you won the heart of the finest mare in all of Equestria."

"I know. And don't worry Mr. Trenderhoof, if you just stick to being yourself and not worry to much about impressing others then you'll find your very special somepony someday." Richie smiled.

"I...thank you for being understanding and compassionate about this." Trenderhoof smiled, touched by Richie not acting like a possessive jealous boyfriend. "Please, call me Trend."

"Only if you call me Richie." Richie chuckled, extending his hoof.

"Deal." Trenderhoof shook it. "I'm looking forward to tomorrow's interview."

"So am I." Richie smiled.

They said their goodbyes and went their separate ways. Richie and Applejack continued on into the hotel and up to the room where she and her friends were staying.

"Well...goodnight." Applejack said awkwardly.

"Goodnight." Richie said awkwardly.

They hesitated. Should they kiss now, or should they wait until later? Deep down Richie did want to kiss her, but he didn't know whether she was ready or not. And Applejack did feel a desire to kiss him, but she didn't know whether it was too early or not.

"OH JUST KISS ALREADY!" Pinkie's voice screamed through the door.

"Pinkie!" Twilight's voice said irritatedly.

Richie and Applejack then heard the sound of bodies falling onto the floor. Caught off-guard, Applejack opened the door to see Twilight and Rainbow Dash pinning Pinkie to the floor and muzzling her with their hooves. Twilight and Rainbow Dash grinned embarrassedly upon seeing Applejack and Richie stare at them. Rarity just facepalmed at the whole thing.

"Heh, maybe we should save our first kiss for later." Richie smirked.

"Yeah, especially since there's somepony I need to take care of right now." Applejack smirked back.

Twilight and Rainbow Dash got out of the way just as Applejack tackled Pinkie.

"Okay cuz, if yer gonna invade other ponies' privacies then yer gonna have to suffer the consequences." Applejack grinned before noogying Pinkie.

Richie, Rainbow Dash, and Twilight laughed and Rarity politely chuckled at the scene.

"Okay okay! Uncle! Uncle!" Pinkie cried.

Applejack let her go, and the two of them laughed.

"Applejack, would you like to go out to dinner again tomorrow night?" Richie asked.

"Sure, but how about we make it a picnic in the park instead of a meal in a restaurant?" Applejack suggested.

"Sounds great to me. Well, goodnight everypony." Richie smiled before leaving.

Applejack and her friends said their goodnights too.

"So, how'd it go?" Rainbow Dash asked.

"It went great gals. I can see myself dating Richie for a long time." Applejack smiled. "However I want Granny Smith, Big Mac, and Apple Bloom to get to know Richie some more before making it official. So I'm thinking of inviting Richie to Sweet Apple Acres after the celebration."

"That's a good idea, there's no sense in ending up with somepony your family doesn't like." Twilight agreed.

"Although I'm certain your family will love Richie." Rarity smiled.

"Yeah, who wouldn't love a guy like Richie? Well maybe a meanie-pants, but that's not surprising." Pinkie grinned.

"True." Applejack chuckled.

That afternoon Trenderhoof interviewed Richie, and the two became good friends during it. When Richie brought up the secret passageways in his home Trenderhoof expressed concern towards the orphans finding out, but Richie reassured him that he used a spell to seal up the secret entrances back before the painters had even started working on the bedrooms. Nopony can get into the secret passageways without Richie casting another spell to open the entrances now.

Later that night Richie and Applejack had their picnic in the park. And after dessert, they finally had their first kiss. The love they felt from it was so strong that for a long time Applejack stopped being afraid of how they were going to balance their jobs and dating. And as for Richie, the emptiness he had felt ever since his parents died was finally filled.