Even when compared to all the rest of what had been happening between him and his friends, Spike had to admit that his visit to Rarity was perhaps the most uncomfortable moment yet. He had never intended for things to get as bad as they had done, nor had he ever wanted to cause her any alarm or stress as he had. Thankfully for both of them, they'd managed to work past it and did what they could to enjoy their time together for a few days. In that time, he was often reminded of why he'd once been so obsessed with her as a child, and in time even she couldn't help but smile when she looked at him.

But, as with all these visits so far, it had eventually come to an end, and it was time for him to move onto his next friend. This time it was Ponyville's resident party planner, Pinkie Pie. The bubbly pink earth pony was, perhaps, the one friend Spike understood the least. Having grown up with Twilight for most of his life, he too had developed a mind that generally appreciated order and logic, so a mare like Pinkie was often hard to grasp. During his early years in Ponyville, she'd often been completely random or hectic in her words and her actions, though unlike a person like Discord, there had never been any maliciousness to it.

Even so, her behaviour could be somewhat overbearing at times, at least back when he first knew her. Thankfully, she'd calmed down a great deal in the subsequent years of his time in this town, so it was unlikely that he'd have much to worry about by being with her for such a long time. So, having left Carousel Boutique, he made his way down to Sugar Cube Corner, which had been in business ever since he arrived in Ponyville all those years ago. Opening the door, he entered, which was at times difficult because of his larger-than-pony size, and he looked around. There, standing at the desk, was a young unicorn mare with a bright orange mane, who smiled at Spike once he entered.

"Hey there, Spike! Long time no see!"

Spike smiled at the mare.

"Good to see you too, Pumpkin."

Pumpkin Cake, and her brother, Pound, had been born just a couple of years after Spike and Twilight moved here. It was still strange to see them all grown up, but then again, the same could be said of Spike himself in the eyes of his friends. Still, he was here for a reason and knew what to ask of her.

"Pinkie here?"

Pumpkin nodded.

"Yeah. My brother and my folks are away for a few days on a long-term delivery, so Pinkie doesn't have as much to do today. She's upstairs if you want her."

Spike nodded in appreciation over that. Unlike Rarity, it seemed that Pinkie wouldn't have anything else going on right now, which was a plus as far as he was concerned. So, he made his way upstairs to Pinkie's apartment which, as it always was, was adorned with a number of different party treats, including her trademark balloons, streamers, and a few banners. To his surprise, there was a new banner just above the entrance of the stairwell which read "Hello Spike!" in big bright colours. He took a moment to chuckle at that, now thinking he was foolish not to expect Pinkie of all ponies to do something like this.

And speaking of whom, the mare in question now came into view once he was fully on the top floor. The pink earth pony bore a massive smile on her face as she rushed towards the young drake.

"Hiya, Spike!"

Spike smiled at her.

"Hello to you too, Pinkie. That place look great. But you really shouldn't have gone to so much trouble."

Pinkie suddenly looked quite shocked at that statement as she gave one of her familiar gasps at Spike's words.

"But of course I'd go to all this trouble! You've been feeling so down in the dumps because of this and I just wanted to turn that frown..."

Before Spike could stop her, she reached forward, grabbed the corners of his mouth, and pulled them up so he was forced to smile.

"...upside down!"

Only once she'd finished saying that did she let go of Spike, whose mouth then dropped down into it's normal position. Raising a claw, he rubbed his cheek, which was now sore from having been pulled like that. He did not begrudge Pinkie for being this way. Quite the contrary, he actually appreciated her a great deal for this. For as long as he'd known her, Pinkie's goal in life had been one thing and one thing only, to make others happy. If somepony was feeling down, she'd be there for them. It was a trait Spike couldn't help but admire, and he afforded himself a chuckle, the sound of which led to Pinkie smiling even wider, which Spike didn't think was even possible.

"That's the spirit! Now come on! I baked a cake and everything!"

Spike looked on as Pinkie grabbed onto one of his arms and started dragging him further into her apartment. Though, much like his Birthday party a few days ago, she was nowhere near strong enough to actually pull him, so his movements were more a case of him indulging her than anything. Once they were in the middle of her room though, he looked down at the cake she mentioned. To her credit, it looked delicious, but then , he knew it would be. The Cakes wouldn't have hired her as a worker in their shop for all these years if she didn't know how to bake a good cake. It was covered in bright pink icing and, as Spike could see, had icing in the shape of her and his heads on top, both of which were smiling.

It was an endearing sight, to say the least, but even so, he looked to his future mate with a somewhat serious expression.

"Pinkie, you DO know what you and I are expected to do, right?"

Pinkie gave a snort and rolled her eyes at that.

"Well duh! It means we get to be bed buddies!"

Spike looked at her with a raised eyebrow and more than a little disbelief over her choice of words.

"Well...I've never heard anypony call it that before."

To his surprise, Pinkie gave a brief giggle before placing one hoof on his shoulder.

"Relax, Spike, I know what you mean. I was here eleven months before the Cake twins were born, and these walls are pretty much paper-thin when it comes to sound."

That was not a statement he ever thought he'd hear from her, but regardless, it achieved the expected effect, as his face became tinted with a blush on his cheeks. It was a sight Pinkie couldn't help but giggle at, much to Spike's annoyance. When her laughter eventually died down, which was a fair amount of time, she let out a sight and looked at him, her expression now one of curiosity.

"Think you'll be ready for it?"

One didn't need to be a genius to figure out what Pinkie was referring to, but even so, it was still a topic that made Spike nervous to discuss. The thought of having to do such a thing to any of his closest friends was surreal enough, but the fact that he was expected to do it to all six was something else entirely. The actual act of it though, as one might expect, was something Spike had been trying hard not to think about too much. Even so, he knew he'd eventually have to discuss it, and Pinkie's prompt just now meant that this was probably as good a time as any.

"Well...obviously I thought about this sort of thing when I was growing up. But I never had the chance to...er...act on it. I'm sure I'll be ready when the time comes, but...I'll be honest, I probably won't have any idea what I'm doing."

It wasn't something that anypony would feel comfortable admitting to, but there it was. He'd spent such a long time dwelling on just how much this change in him would affect his relationships that he'd completely neglected the very obvious fact that he'd never once had intimate relations with anypony. That thought now took centre stage in his mind, and he began to worry about his first time with his future mates. He was distracted from such thoughts however by the feeling of Pinkie tapping on his claw with her hoof, gaining his attention. As usual, there was a smile upon her face, but it was not the massively happy one most were used to seeing on her, but rather a more understanding one.

"Don't you worry, Spike. Auntie Pinkie will tell you everything you need to know."

Under normal circumstances, Spike might be inclined to tell Pinkie that her use of the term "Auntie" to describe herself was getting a bit old, to say nothing of how awkward it made their current predicament. But instead, he was focused on what she'd just said to him, and his face changed into one of surprise.

"Oh! So you've...?"

Pinkie looked at him and nodded, and rather enthusiastically at that. It was only now that Spike suddenly realised just how little he knew about the kinds of things Pinkie got up to. His other friends he knew for certain had never been involved with another pony before, for one reason or another, so he was more than a little surprised to not only find out that Pinkie had crossed that line previously, but even more surprisingly, that she'd actually managed to keep quiet about something for once. He was certain that, had such a thing occurred, she'd be bouncing around telling all her friends about it, much to the chagrin of the stallion in question. And speaking of whom, it was now Spike's turn to be curious.

"Um...if I may ask, who...?"

The pink earth pony looked off, a somewhat nostalgic look in her eyes.

"Oh, it was ages ago. An old party-planning rival of mine. Haven't seen him in years though."

There was a part of him that wanted to enquire further, as well as trying to rack his brain to think about who Pinkie might have been referring to. Unfortunately for him, Pinkie took hold of his arm and began dragging him away, which he once more indulged her with by moving of his own accord.

"Now then, I'm no expert or anything, but I can teach you a few pointers, if you're interested We don't need to do anything physical yet, just so you know. Just me telling you what works. You okay with that?"

Spike considered that for a moment. Though it would have been a lie to say that he wasn't just a little bit jealous that he wasn't going to be Pinkie's first, he was actually quite grateful that there was going to be somepony around to tell him about this sort of thing. Truth be told, he'd have most likely gone off to the library to find out some book on the subject, and he knew deep down that Twilight would probably keep him there and subject him to some kind of biology lecture to bring him up to speed, which was not something he was keen on experiencing. Hearing it from somepony who had actual hooves-on experience was quite a boon for him.

"Yes. And thank you. Faust knows I'd probably just look stupid otherwise."

Pinkie smiled back at him, happy that he'd accepted her offer of help. Spike could, for the first time in a while, breathe a sigh of relief, knowing that, at the very least, this one part of the whole experience wasn't going to be something he was going to have to walk in blind about. But, his sense of relief dwindled somewhat as he looked to Pinkie, who was now running a hoof through her mane and looking thoughtful about something. After a few brief moments of silence, she looked him in the eye and spoke.

"Spike? How would you feel if, when we have our first time together, I wore my mane straight?"

For reasons he would never understand, the young dragon suddenly felt a very cold chill crawl up his spine when he heard those words.