Co-written with Trahzo, who I a big thanks to for helping me with this requested mare. Big thanks DanvilleBengal for the mare's name.

Spike, after getting his heart broken by Marshmallow witch, AKA Rarity, has now had his hardworking heart broken yet again by Sweetie Belle! After his crush with Rarity had a falling out, he directed his attention towards Sweetie Belle But that guy Button Mash had her in his sights as well! Both clashed a non violent battle to win the affections of a beautiful singer, sadly it was all for naught as Button Mash managed to put an end to this rivalry with him as the winner! After that Spike gave-up on love, until one day a certain milf appeared for him to have his revenge of Button Mash.

Said milf mare was talking with him as he had come over to Button's house to call off their rivalry, but that's how he met the youthful looking mare.

"I really hope that after you & Button call off this rivalry you 2 can be friends again & cosplay Skylanders like you 2 used to." Said Button's Mom.

"Well it might be a little harder than you think to call this off." replied Spike.

"Huh? Why do you say that?" She asked.

"He's dating my 2nd crush, and they're inseparable!"

"I know, every time I see them, it reminds me of me & my husband...before..."

"Oh yeah, that was tragic. He didn't see the cyclops coming until it was too late..."

"*sniff*"

"H-hey don't cry, I'm sure he'd want you to move on."

"Yeah, I'll move on to the great beyond after Button finishes College, or at least when Sweetie Belle graduates college, they get married have a kid, then the cycle of death shall continue!" She said.

"I'm sure you'll find a nice guy easy. You have experience raising a kid, you managed to keep a heart o gold, and you don't need makeup thanks to your natural youthful look."

"Oh stop it, I'm not that young."

"Come-on, you can visit a high school & no-one could tell that you're an adult." Spike complimented. Spike then tried holding back his nosebleed from the thought.

"Well you're quite the sly dragon aren't you?" teased Button's mom with a giggle.

Spike then had a light bulb! Maybe he can get lucky & revenge at the same time, and this mare in front of him is the key!

"Yeah, as you can see I've just stolen a laugh from you." Sly Cooper reference for the win!

"Well thank you." smiled Milano.

They looked at each other with bedroom eyes for a few seconds until Milano realized what was going on.

'Oh-no! D-did I just fall for a kid? Nope! Nope! Nope! He's too young!' She thought. 'I mean, that's just sick how dare I? I'd never date a kid.'

Meanwhile in every universe she's dating a kid, and maybe even banging one.

'Hmph, looks like I've got the fish, now to reel her in.' Spike deviously thought.

"You know, I know this great doughnut shop up in Canterlot. Maybe we could spend some time and I can show you that it has the greatest donuts in all of Equestria."

"Oh, I don't know."

"Just hire a babysitter, and then we can go."

"Alright..." Then Milano called Vicky the babysitter. "There."

"Great, now let's go!" Then he took Milano by the hoof.

'Wait, did I just agree to a date? Am I really that lonely?'

Spike paid for their tickets to the train as they took their seats and waited to reach Canterlot.

"I haven't been to Canterlot since..." Then she looked down.

"Like I said, he'd want you to move on." Spike told her.

"It just hurts every time I think about it." she replied feeling fresh tears in her eyes.

Spike, being the smooth guy he is, tries to cheer her up.

"Hey, look here."

"Huh?"

"You could use a handkerchief, or rather, a dozen handkerchiefs." Then he pulled handkerchiefs out of his mouth, making Milano laugh.

"You're silly." smiled Milano wiping her eyes.

"Heh, hey if Pinkie isn't available to bring a smile, I gotta step up. Same thing happened my friends switched cutie marks."

"Well, you're a natural at it." Then Milano rubbed Spike's forehead.

'Alright, you got her to put her hooves on you spike, you're so smooth. DAMMIT SPIKE, IF YOU'RE THIS SMOOTH, THEN WHY DID YOU LOOSE SWEETIE BELLE TO BUTTON MASH?!!!'

While he was berating himself, Milano noticed they reached Canterlot.

"Huh, guess we're here, come along miss.....uh......"

"It's Milano."

"Yes, come along Miss Milano, the doughnuts wait for no-one." Spike got off the train 1st, then bowed his head. "After you mademoiselle?" He said politely.

" *giggle* Merci beaucoup petit monseir."

"Hmph I may be small, but I'll one day grow up to be Godzilla."

"But today, you're just a cutie."

Spike blushed as he lead the way to the doughnut shop.

As soon as they entered.

"Well, as I live & breath, my favorite costumer Spike, finally got a date, and may I say a real hotty at that."

"Donut Joe, would you not, I don't want your Captain Ressentiment mouth to scare away my new friend." Then he blinked in morse code. 'She wont be for long' and Donut Joe understood.

"Do you have something in your eye?" She asked.

"Nope, I'm fine."

"What can i get for you two?" asked Donut Joe.

"You know my usual." Spike said.

"I don't know what I want." Said Milano.

"Don't worry Milano, I'm treating you."

"Oh, well in that case I'll have the Heartfelt Rose."

"Ooh, you got yourself a romantic here Spike."

"I know that." smiled Spike winking at Milano.

Milano blushed from Spike's words. 'Am....am I really ready to let go?'

Then....wait a minute, a musical number?

"Oh am I truly ready to let go of my paaast love?
Am I truly ready to let gooooo him?
Can this one give me, the world just like you?
Is it right to let him intooooooooo...
My heaaaaaaaaart?"

Okay, after that strange scene, we return to the doughnut shop.

"Did you just feel that wind kid?"

"Yep, sounded like a love song music video fantasy, which means I'm close to winning entrance into her heart. 'And a step closer to getting my revenge.'

"Well I hope that means you two have good luck in your relationship. I mean, it's not like you are purposely dating her to get revenge on some guy who stole your love."

"Yep, nothing like that at all, and I really hope we don't get a reprisal."

"Alright, I'll get your doughnuts ready in a jiffy, it's been a slow day."

Later...their doughnuts arrived.

Milano was amazed to see Spike eat away at the large pile on his plate like it was nothing. "Wow, you must be outstanding at eating contests."

"Got 1st place in a marshmallow eating contest, carrot dog eating contest, and 2nd place in a doughnut eating contest."

"2nd place?"

"Yeah, Doughnut Joe's cousin beat me in that one."

Then Milano & Joe laughed at that. Joe laughed because Spike & Joe have an insult friendship where they make fun of each other but all in good fun. Milano laughed because she liked the story. Both enjoyed their pastries as they finished them in record time.

"Here are your bits Joe."

"Thank you Spike, and have fun in Canterlot." He called out as they were exiting.

"I cannot tell who's doughnuts are better, his or the one's in Sugarcube Corner."

"Yeah, my stomach has had a heated debate with my other organs for years."

Then she laughed at that remark. Soon they made it to a park where they sat on one of the benches.

"I used to come here a lot. Either it be Twilight's parents or my..." Then Spike began to cringe.

"Your who?"

"My own Ex girlfriend."

"You had a girlfriend before?"

"Yeah, her name was Moon Dancer, we broke up before me & Twilight moved to Ponyville."

"Aww, but I'm sure you 2 are still great friends."

"Honestly, no! When I came for royal business I tried to reconnect with her, but she started hanging out with a bad crowd just because I left her. I didn't have a choice, I had to make sure Twilight doesn't eat junk food when in Ponyville! Then she was on my case about so you chose that social napalm over me to make sure she doesn't get fat? Oh, maybe I should have attempted getting fat so you wouldn't leave me!" Then after reminiscing of the events, he began to cry. "I'm sorry you have to see me like this, but it's just became so hard for me to find a girl!"

Milano looked at him sadly before pulling him into a hug she would use to help her son.

"Thank you Milano, I needed that."

"Don't worry Spike."

"The time I've spent with you has now driven me to regret for what I was planning on doing with you."

"What were you gonna do to me?"

Then Spike realized he had said something he shouldn't have. 'Damn it! Now I'm bucked. Well, guess I gotta come clean.'

"Spike, out with it now young man!"

Then Spike looked at her, hoping for mercy. "I was gonna use you to get revenge on Button Mash for stealing Sweetie Belle." Then Spike hopped off the bench. "I know, I'm despicable of me to do that, I'm sorry if our time together was a lie, but truth be told, I had fun today, I really did." Then Spike slumped away back to the castle, but that's when a hoof stopped Spike.

"Hold up right there. I admit, every fiber in my body is screaming at me to punt you like a football, but I did enjoy today. The only thing I have to know is this. Do you truly care about me? Or am I just a mare for you to use and throw away?"

"You were just a mare to me at 1st, but as the time went on, talking to you, comforting you, making you laugh, looking at your wonderful figure as you ate, comforting me...it made me realize that you're a very wonderful mare and made me want to care about you, I honestly felt bad about your husband's death & trying to make you forget about him so you can truly be happy was part of my honesty."

Milano narrowed her eyes and looked directly into Spike's eyes to see that he was telling the truth. "Spike, it warms my heart how you've been sweet to me this whole time, making me feel better regardless of it being an act of revenge, and I have actually fallen for you."

"It does?"

"It really does." Then Milano picked Spike up with her front hooves, the wind began blowing her hair tie off making it flow wildly, and oh yeah it was also sunset.

"Spike?"

"Yeah? 'Oh Bonnie Zecherle no! She's not gonna...'

Too late Spike, and for those of you who do not know who Bonnie Zecherle is, she is the creator of the G1 Ponies, the true God of MLP, or rather Goddess, anyways let's just get to Milano's reprisal.

"You, have really touched my heart and filled with, your own love.
You've made me so happy, that I cannot believe this love!
And the fact, that you have had fuuuuuun with me.
It makes me feeeeel....makes me feel that this what I was missing!
It's been a while since I've felt love like thiiiiis!
You're the one who's filled the void in my heart!
I thank you for this time we've had.
And now for the rewaaaaaaard,
A kiss form the one you find so lovelyyyyyyyyy"

Then as everyone was clapping for her amazing voice, she & Spike kissed in the sunset.

"Aww, look at that Discord, why can't we be like that?" Asked Celestia as she's lowering the sun.

Discord just looked away because he was being tsundere to Celestia.