As Maple shut the door she gave him some encouragement and made him start walking toward town. As he grew nearer he could see the sun setting, which made him gulp as he could feel his nerves act up. But he shook his head knowing that this is what he wanted.
He knew he was close to the post office and he couldn't stop thinking that it was stupid of him to dress up. After all, Winona is a wild spirit who likes to get dirty. But he once again shook his head and knew that's why Rarity made him a simple plain shirt. To top it off he knew the gems were magically glued onto the collar, so he knew that wouldn't be an issue.
<Hey Spike!> He was snapped back to reality as he heard Winona call him, and when he saw her he couldn't help but blush.
Though it wasn't really as to what she was wearing, he just couldn't believe she agreed to this date. But what she was wearing didn't hurt, in fact, he could tell it was a Rarity original dog dress. He knew because she had been wanting to do pet fashion for a minute, but the way he knew this one in particular was because of the well-aged fire ruby sewn into the front.
<You look very handsome Spike, I really like your collar.> Winona said making him blush.
<Y-you look nice too, especially with that fire ruby.> He replied making her blush in return.
<Y-yeah, I heard Rarity talking to my pony and said that you would know what kind of gem it is. Something about it having meaning to both you and her, but also wanted to show her support for you.> Winona spat off fast, and that made him know for sure how nervous she was.
<So, um, since we're here what's the plan?> He asked hoping it would cut the nervous energy.
<Oh, right, well come on and follow me!> Winona replied as she turned and started to walk making him follow. <These outfits will probably take a little beating tonight.>
<I'm sure Rarity thought of that, which can't you tell me anything about what we're doing?> He asked.
<Nope, oh, by the way, I see that your leg is healed. How did that happen?> Winona replied and asked making him want to paw palm.
<Don't know, some kind of magic. Maple said she has an idea of what happened.> He answered making Winona give a small nod.
<You know, I like Maple. She is very smart and nice, hard to believe she's a, or was I should say, a wild Timberwolf.> Winona said.
<Yeah, she definitely adjusted to life here.> He mentioned.
<Well, you know what I like about her the most?> Winona asked.
<What's that?> He replied with a tone of actual curiosity.
<How supportive she is to you, I think she really helped you more than anypony else could.> Winona answered stopping to look him in the eyes.
<Y-yeah, and that reminds me I have a little surprise for you as well.> He said making Winona tilt her head in curiosity.
<Let me guess, you aren't gonna tell now?> Winona asked.
<I-I could, but not right now. I want to see what you have planned first.> He replied.
<Well, now I'm really excited, but we have a long ways to go.> Winona said and started walking again.
While they walked they made some small talk, both were nervous and excited about the date. Though he couldn't help but think of how nice she looked in her outfit. For him it made it feel like a real date, not that it wouldn't have been but it did help him relax in a strange way.
<We're almost there, can't wait for it to begin! I mean what I had planned was going to be fun and all, but I can't help but to wonder what you want to say! I mean when do you want to say it? Beginning? End?> Winona asked practically jumping up and down in excitement.
<Um, uh, w-well I think I would like to say it when I think it's time, no offense.> He answered.
<None taken, I understand. I mean if it's important then you should say it when you say it, though keep in mind there is such a thing as waiting too long. Besides I think you'll like what I have set up, had to pull in a lot of favors for it!> Winona said before suddenly stopping mid-bounce.
<Why'd you stop?> He asked.
<We're here silly! But we are a little early so we'll have to wait a moment until the sun goes completely down and the moon rises, which you know it's supposed to be a full moon tonight?> Winona asked as he sat down next to her.
<Yeah, but can't you give me a little hint as to what we're supposed to be doing?> He replied.
<Well, we watch the sky and I'm sure you'll see it.> Winona answered making him shrug his shoulders.
<So, about what I want to tell you...> He started making Winona lock eyes with him.
<Y-yeah...> Winona said.
<I-I made my mind up about something, something that's very important.> He said, taking a deep breath though before he could say another word a bright streak came out of the trees and into the sky.
<It's starting! I'm sorry, but can it wait?> Winona asked, though he could tell he had caught her attention so he nodded in agreement.