Note: The "blackmailing" part of the title only applies to the first two.
Soulsilvershipping
It is so easy.
"Silvy, take me out to dinner," Lyra begged as she clung onto her boyfriend and gave him her best puppy eyes.
"No," replied the redhead, without any hesitation whatsoever.
Disappointed that Silver was no longer fazed by her puppy eyes, Lyra puffed her cheeks in annoyance. But a sly grin immediately appeared on her lips since she knew exactly what to do to change Silver's attitude.
Lyra pretended to give up as she turned away, which surprised Silver greatly. Lyra was not known for giving up easily, especially after a single attempt.
"I guess you really won't take me out to dinner," she opened her Pokegear, "so I'll just ask G–"
Before Lyra could even finish uttering the name of her childhood friend, Silver cut her off by snatching her pink Pokegear out of her hands and immediately closing it.
"Where to?"
Lyra giggled. It worked every time.
Oldrivalshipping
Though it does take time, Blue always, somehow, gets what she wants.
It was just another quiet and peaceful day for Green; perfect for a productive session of research. That is, until he heard a familiar voice calling his name from downstairs.
"GREEN!" shouted the very excited voice, which, upon immediately realizing who the voice belonged to, made Green contemplate jumping down the window and joining Red at Mt. Silver.
As usual, Green tried his best to ignore the source of the noise, and as usual, Blue made that to be impossible as she flew into his room and jumped onto his lap.
Green sighed. "Let me guess. You want me to buy you dinner."
And before Green could give his usual answer, Blue put her finger on his lips and said, "And let me guess. You're too busy."
"You know me so well," replied Green as he reached for his stack of research papers on his desk.
Blue pouted. "But Greeeeeeeeeeen! That's no way to treat a lady! Any man with some decency would take a lady out to dinner if that is what she desires. And have I mentioned what a generous and nice person you are?"
Under normal circumstances, Green would've avoided conversation by physically dragging Blue out of his house, but he decided that Blue got a taste of her own medicine.
"Well, Blue," he started, "I accept your compliments, but are you not a strong, independent woman who is capable of living on without men spoiling you? I cannot see why such a capable woman such as yourself would need me to do anything?"
It was definitely enough to shock Blue for a moment, as she was staring at him, her mouth agape. However, it was not enough to make her give up, for nobody ever succeeded in such a thing.
"Well, Green," said Blue as she stood up and headed towards the door, "It appears that you won't take me out to dinner no matter what I said. It is a shame, but I suppose I'll just have one of my juniors to treat me then. Gold owes me a couple of favors, Ruby wouldn't refuse, Diamond could just cook something, or I could just ask Red…"
Green put away his stack of research papers and sighed again. "Fine. I suppose capable women would appreciate being treated every now and then."
Blue smiled and tackled Green in a hug, gleeful that her tactics worked once again. "Yay! You're the best, Green! And I love you!"
"...Pesky woman."
Specialshipping
There is no blackmailing. In fact, they wouldn't even ask each other for such things.
It was a normal day for Red as he was, as he would do every single day, training with his Pokemon.
It was then when Blue emerged out of a nearby tree and without any greetings whatsoever, she suddenly suggested, "Red! You should take Yellow out to dinner!"
Instead of replying, Red screamed, which was quite expected considering the fact that Blue basically just appeared out of nowhere.
"Jeez. No need to act so surprised."
"But why?" asked Red, confused as to why Yellow would need to be fed dinner by him."Yellow is not dying from lack of food or anything."
Blue could not believe just how dense Red was. However, she was not willing to deal with this today, which is why she simply demanded, "Just do as I say!"
"Okay," Red agreed even though he still didn't understand why. He took Aero out of his Poke-ball and promptly flew to the doorstep of Yellow's house in Viridian City.
He knocked on the door, and soon after, a certain blonde haired maiden opened the door.
Before Yellow could even greet him, Red grabbed Yellow's hands and asked, "Would you like to eat dinner with me?"
Yellow blushed at the rather abrupt invitation, but of course, she happily accepted it. "S-sure, Red-san."
Franticshipping
It's always a competition. Always.
"Prissy boy! Take meh out to dinner!"
Ruby raised an eyebrow at the sudden demand from his sapphire-eyed girlfriend. "Why should I buy you dinner?"
Sapphire recalled what Blue had told her beforehand. "Because you're a boy, and boys hafta buy dinner for their girlfriends!"
"I thought we have already established that gender roles cannot apply to the two of us?" Ruby stated as he pointed to himself and then Sapphire.
Then, he had a brilliant idea. "How about, the last person to come back home with a ribbon or a badge has to buy the other person dinner?" he suggested.
"But I already got every badge from Hoenn, and you've already got all five ribbons."
Sapphire made a fair point, which is why after a brief moment of contemplation, Ruby replied, "Then, we'll pay a visit to Sinnoh!"
"Deal!"
Sapphire agreed as she jumped out of the window to catch the nearest flight to Sinnoh with Ruby shortly following after, except that he properly used the stairs instead of jumping out the window like an uncivilized person.