All 18 Major Romantic Relationships on Friends Explained and Ranked By Normalcy (6 of 9)

Monica and “Fun” Bobby (Season 1)

Monica’s fling with Bobby started off fun and carefree. His charm and outgoing personality were a breath of fresh air, and Monica really felt like they had long-term potential. But beneath the surface lurked a dependence on alcohol that fueled his “fun” side. Monica, despite her initial attraction, couldn’t reconcile his messy habits and drinking with her own desire for order. Ultimately, she helped Bobby recognize his problem, but their romance fizzled out when, ironically, he believed she had a drinking problem.

Ross and Emily (Season 4)

Ross’s whirlwind romance with Emily felt destined. A quick proposal led to a London wedding. However, fate (and Ross’s lingering feelings for Rachel) intervened. The infamous “Rachel” altar moment shattered their future. Despite a brief attempt to salvage things, their relationship ultimately succumbed to the weight of past wounds and unspoken emotions, leaving Ross and Emily to navigate the aftermath with a heavy heart.