Phoebe Buffay’s attitude toward Chandler Bing was a real head-scratcher in the later seasons of Friends. Her constant remarks about him not being good enough for Monica grated on many viewers’ nerves—myself included. She seemed to revel in the idea of their breakup, even trying to orchestrate it a couple of times. Remember when she brought up Monica’s lunch with Richard? Or when she revealed Monica’s intention to hook up with Joey? It’s hard to chalk these up to mere “slips,” especially since Phoebe didn’t show much remorse afterward.
Some fans might argue that Chandler got what he deserved, given his history of teasing the group. But here’s the thing: Chandler’s jokes were mainly a way for him to connect with his friends. He never intended to hurt feelings. On the other hand, Phoebe aimed at Chandler in a mean-spirited way. She insulted others, too, but her digs at Chandler often felt more personal. Perhaps naming her brother’s kid after him was her way of keeping him from changing his name—but that was before he even got together with Monica, adding to the puzzle.
While I realize the writers probably used Phoebe for comic relief or to push the plot forward, her consistent disdain for Chandler became a notable character trait. It’s a shame because earlier seasons showcased some sweet moments between the two. So, naturally, I couldn’t help but overthink it. What could cause this in-universe shift? Here’s my theory, which I consider my friend’s headcanon: Phoebe had a crush on Monica.
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Let’s break this down. It’s established in the series that Phoebe, while not openly bi, had some bisexual tendencies. She swooned over Cousin Cassie and kissed Rachel to see “what the fuss was about.” Her colorful romantic history makes it believable that she had feelings for women. Now, consider Phoebe’s relationship with Monica. Despite moving out because Monica drove her up the wall, she valued their friendship deeply. When Rachel joined the group in Season One, Phoebe’s closest bond remained with Monica. Such strong attachments could quickly evolve into romantic feelings, especially if Phoebe felt the need to hide them, knowing Monica didn’t share her attraction to women.
When Monica started dating Chandler, things turned sour. Phoebe tolerated Chandler until then but now had to see him regularly. The woman she adored ended up with a guy she viewed as a “sarcastic, good-for-nothing emotional basket case.” No wonder she lashed out! This was the only way for Phoebe to vent her frustrations without jeopardizing her friendship with Monica. In her eyes, Chandler didn’t match Monica’s “level,” yet she had to cope to keep that connection alive.
Now, Rachel did throw a few jabs at Chandler, but less often than Phoebe. Maybe Phoebe’s disdain rubbed off on her. If I recall correctly, Rachel’s digs were limited to a couple of forced living situations.
In the end, while Phoebe finds her soulmate in Mike and ties the knot, I suspect she never truly respects Chandler as Monica’s match. Her constant criticisms were probably more about her unacknowledged feelings than Chandler himself. So, the next time you watch Friends and notice Phoebe’s digs at Chandler, consider this headcanon—because in the chaotic world of Friends, love and friendship were rarely straightforward!
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