We do have a lot of groups here that show shipping of MLP characters within the same generations, so I thought what would be a like to ship MLP characters of different generations. Maybe there are some that really can work. If anyone can think of characters from different generations that go together, then post them here and state why. To start off, I think that both Twilight Sparkle and Megan Williams go together for good reasons. Both of them are known leaders of their groups. Another thing is that they both became heroes by accident when they first started, though for Megan, she was just dragged in, while Twilight chose to fight despite not being told to do so originally. Although not actually stated, Megan probably never had much time to make actual friends in her own world due to have to do much work on her family's farm when not being at school unless she may have been homeschooled along with Danny and Molly, but this was never mentioned in the series. Meanwhile, Twilight originally didn't make friends due to being much of a bookworm and originally felt that friends weren't that important to her, but that changed when having to go after Nightmare Moon for her first adventure. Nonetheless, I do think that they go together, and there are some pictures I found online to prove that. Still, tell us what other characters from different generations go together.

It's too bad that when Volume 3 of the MLP Manga came out, they made Megan miss out when it came to Twilight's chapter, which took away a chance encounter she could have had with Twilight not to mention gave her a big snub that didn't go well with G1 fans.

I take it that nobody can think of any other characters from different generations to ship together.