---Tails---
This two-tailed fox wasn't very good at dating. In fact, he has never been in a real relationship. When the young genius needed advice to ask you out, he made the poor choice of asking his adoptive older brother, Sonic. Only problem was, he wanted to keep his current friendship with you a secret, but he wasn't very good at hiding things from his best friend.
"So, why do you want dating advice?" Sonic asked with a smirk.
"Uh, I-I'm just curious," the fox lied.
"C'mon little bud, who is she?" the hedgehog questioned as he nudged his little brother.
If the young genius had learned anything from the fastest thing alive, it was that reverse psychology was one of Sonic's weaknesses. "Maybe you can't teach me; I'll just have to go ask Knuckles. After all, the guy must be amazing with the women," Tails stated as he began walking away.
"No Way!!" the teenager retorted as he pulled his sidekick back. "I'll teach you everything you want to know; no questions asked."
After his little lesson in love, Tails flew off to find you in the forest. You were feeding some birds when your male friend arrived. You weren't expecting him to be wearing a pair of sunglasses in the middle of the night, though.
"Hey there, cutie," the fox welcomed as he brushed his hair back with his fingers.
"Um, Tails?" You asked as you approached your friend. "Were you bit by that snake yesterday? You're acting very strange."
"D-don't you think it's cool?" the genius asked as he pulled off the dark shades.
"You're a child genius who fights robots and saves the world!!" you exclaimed. "You're already cool!! Who would tell you to try to be cooler?"
"Someone who stinks at dating advice," Tails muttered.
"Dating advice?"
The young fox paused in shock before scratching the top of his head while stuttering, "uh...y-yeah, I wanted t-to ask you o-out on a d..d...,"
"On a date?" you finished.
"You don't h-have to if y-you..." the two-tailed male began, but you interrupted with a tight hug.
"I would love to!!" you answered.
---Knuckles--- The research became boring, and you would find yourself reading or exploring the island. Today, you were taking a nap in the lush grove on Angel Island. There was cool shade, a relaxing breeze, and a far distance from the echidna. He had been acting peculiar lately,and he seemed to be getting more and more competitive each day. Maybe it was a side effect to being around the Master Emerald.
You pulled out your favorite book from your bag, and you immersed yourself in the epic tale of heroism and action. You read page after page until a certain guardian came pounding through the forest.
"Yo, (Y/N)," Knuckles called from below. You began climbing higher up the tree.
"What is it red-head?" you asked annoyed.
"You still owe me twenty bucks for the last bet!!"
"I beat you in sharpshooting fair and square," you rebuttled.
"You pushed my off aim," Knuckles argued. "Besides, we didn't use a gun. We used a slingshot."
"I still won, so leave me to read, please."
You began falling into the words once more, but the echidna's voice hollered into your ears. "How about a deal?"
You were intrigued by his offer. You bookmarked your page and closed the novel. "What'cha thinking?"
"You have to spend the entire day with me, and if you last without stepping more than three feet away from me, I'll give ya $50."
"What about if I lose?" you asked. You didn't mention his wrong math.
"If you leave my side before sunset tomorrow, you gotta meet a friend of mine."
You decided not to ask for specifics. After all, you enjoyed a risk. "Alright, I'll go on your little date."
The Knucklehead started walking away, but he made a quick heel turn when your remark settled into his mind.
"IT'S NOT A DATE!!!"
---Mighty---
You had been strolling deeper and deeper into the cavern every day for a week now, and you began feeling less and less afraid of the underground passages. As you traveled further down, you would discover plant fossils, gemstones, and stalactites along with stalagmites. At first, Mighty would push and pull you through the caves, but you we're fully capable of moving on your own now.
"I gotta admit," Mighty stated, "I didn't expect Moss' plan to work so well. I thought it was stupid at first."
"Same here," you agreed as you traced your fingers along a stalactite. "This cavern is amazing. There are so many beautiful gems in here."
"None of them glisten brighter than your smile, though," Mighty replied, making you blush and stop in your tracks.
"W-what?" you asked as you rubbed you arm. Mighty turned to you with red on his cheeks and a small smile or embarrassment.
"Well, y-you're a really nice girl, a-and I was wondering if...uh," the Amarillo stuttered as he rubbed the back of his head.
"Are y-you asking me...?"
"O-on a date?" the red Mobian finished. "Yeah, but I'm cool if you don't. I mean, a girl like you probably has tons of guys on her doorstep, and..."
You pulled Mighty into an unexpected hug with a huge grin on your face. You felt the jewels around you shine brighter, trying to beat your smile's twinkle.
"I would love to!!" you answered as you released the male from your grip.
You couldn't make out who it was, but you could hear chuckling from the outside of the caves. The childish laughter echoed off the walls before saying, "I told ya so!!"
---Espio---
You strolled down the streets of Station Square along side your current guardians, Vector, Espionage, and childish Charmy. You had recently tried snatching a priceless emerald from a museum, and now you weren't allowed to go anywhere without being watched. You even had to wear a tracking device/lie detector on your wrist everyday. It was a pain to sleep with, but you had made an escape plan.
"So, where did ya want to go (Y/N)?" Vector asked as he pulled down his headphones.
"There's this amazing store in the mall I think you guys will love," you answered vaguely.
"What is the name of this, 'store?'" Espio asked as he crossed him arms.
"Here we are!!" you exclaimed as you walked inside a large store.
The three males looked puzzles at the building exterior. With clean windows, white floors, and dressed up mannequins, the guys didn't seem all that excited.
"Wow, (Y/N)," Charmy began sarcastically, "I was wondering when you would notice my love for fall fashions. "
"Are you sure you guys don't want in?" you asked as you began entering the department store. "It's pretty cool."
"I think we can trust you enough to shop," the crocodile answered as he started taking steps back. "Why don't you but some clothes, and we'll meet ya in the food court in an hour?"
You didn't get a chance to respond as they ran away. A small dust cloud in their body shapes disappeared into the air, and you gave a small smirk. As you waltzed into the store, you scanned the area for a certain friend. Once you stopped his tattoos and earrings, you called his name.
"Yo, Harley!! I clothes still have the ink device on them," you stated casually. "Ya mind taking it off?"
You showed him your wrist, and he answered in a silent nod. The red snake pulled out a small device, and he scanned it over your tracing device. The wrist machine was automatically turned off, and he piled a screwdriver to pry it off you. You passed him some cash you stole from Charmy's candy-spending bar, and you left the store.
You didn't even leave the store when you were stopped be a reappearing chameleon. "Did you really think I would leave you alone?" Espio asked as he grabbed your wrist.
"Actually, yeah. Do ya appreciate the fine art of make-up, too? you asked with a smirk.
"Quit the games, your on babysitting duty when we get home."
"NO WAY!!!!" you retorted. "I'm not taking care of some kid!!"
"You need to be punished," the purple ninja stated. "Unless you want to make a deal?"
You glared into his eyes before answering," Sure, what is it?"
"I take you somewhere nice to teach you good manners. You must be kind, courteous, and polite the entire night."
"So, you're using blackmail to get me to go on a date with you?" you asked.
Espio only smirked before walking away. Maybe this guy wasn't such a goody two-shoes after all.