Mindy and Vivian were dating forever before they had an explosive break up when they were in their early 20s. Those two are never ones to do anything less than with full drama so their final fights and break up were just, there was a lot of arguing and things broken and Vivian slapped Mindy in the face. It was kind of amazing. I think the two of them just both had too similar personalities for it to work. It’s really surprising the relationship lasted as long as it did.
On the more amicable side of things, Caleb dated Opal for a good while until Opal realized she preferred being friends and wasn’t really interested in romance at all. Caleb was totally fine with returning to a platonic relationship; the two of them had been good friends before they tried out dating, so it was fairly easy to go back to being friends and not lovers.