[Tony Montana]

Originally Posted by Ant.

Ross and Phoebe
I really think Ross' scientific way of thinking combined with his weird necessity of being right could've been challenged with how open Phoebe was with ideas and how spiritual she was. That became apparent when Phoebe believed her mother came back to life as a cat, and I think if there was to be a relationship between them, it'd have to be that moment (or a similar one). And I think that would've been great for their characters. I don't think Phoebe ever went wild with her head in the clouds but it could've been nice to have Ross keeping her feet on the ground, but Ross certainly would've needed Phoebe to bring him up to the sky.
Ross became a caricature of himself once he broke up with Emily. As Carol said in Season 3, Ross is a good person and a good friend. And he certainly was. He never meant harm and always ****ed up with good intentions. By the later seasons, he's putting his career on the line by sleeping with students, trying to seduce his blood-related cousin, and even tried to jeopardise Rachel's career just so she could stay in NYC (although he did have a change of heart and told her to go for the job in Paris, he also ****ed with her head and told her to get off the plane... so... good deed undone)

I think Phoebe could've loosened him up and could've been a good rebound following his divorce with Emily (sorta like how Ross and Phoebe try and hook up the moment Ross finds out Carol's a lesbian. Talking of that scene, there's a nice air between them. Despite the awkwardness, they're still jokey and it felt right, not forced). Perhaps with Ross being uncomfortable with Chandler and Joey's living situation, he goes to Phoebe for comfort, and thus begins a relationship. Phoebe admits to missing Carol and she already saw Ross (and Monica's) family plenty, so I'm certain she could've easily found the family she forgot she needed in Ross (plus I think becoming closer to Ross and by extension, Ben, could've helped mature her maternal qualities that we very briefly saw when she wanted to keep one of the triplets (although I can't help but wonder why the triplets appeared like, twice after their birth given how Phoebe cared so much about finding and piecing together the family she had when there were kids and a brother there for her anytime she wanted... meh)

tl;dr Ross' family could've given Phoebe the structure her life needed, while her open-mind and free spirit could've helped Ross heal from Emily and stopped him snowballing into the disaster he became

I used to ship them when I was younger