Season 1: 2009-2010
May 23, 2009:
Phoebe walks away from the bonfire party, and meets Damon for the first time. He compels her to forget their conversation, but she later remembers it, when she decides she wants to.
September 9, 2009:
Stefan solidifies his friendship with Phoebe, by bribing her with books.
Phoebe meets Damon for the second time, though she thinks it's for the first time. Damon finds her intriguing, because she doesn't fall over herself trying to please him or get his attention.
September 11, 2009:
Phoebe bonds with Stefan over being forced to blend in, when they didn't want to.
Phoebe bonds with Damon over Elena's dinner party, when he helps her clean up in the kitchen.
September 12, 2009:
Phoebe becomes suspicious of Stefan, after she clearly saw him get hurt and yet somehow healed. She asks Bonnie about the vision she got after touching Stefan. This only reinforces her gut feeling that something is off about Stefan and his brother.
Damon visits Phoebe in her room, after she falls asleep. He tucks her in, and caresses her cheek.
September 24, 2009:
Matt escorts Phoebe to the Founder's Ball, where Damon tells her the story of the "original" Salvatore brothers. The story only feeds her suspicions about him and his brother.
Phoebe connects with Damon on - what she later understands as - her empath side. She knows that there is good in Damon, and that he would never hurt her. Even without knowing that he's a vampire, or what he's capable of, or what he's done in the past; she knows he would always care for her.
September 28, 2009:
While trying to help him score points with her sister, Phoebe's suspicions of Stefan take a strange turn. An encounter with an old man that seemed to recognize Stefan from many years ago - yet Stefan hasn't changed - makes Phoebe begin to think that maybe Stefan is a vampire.
September 29, 2009:
Phoebe begins asking questions and collecting evidence on Stefan potentially being a vampire. When she thinks she has enough, she shares it with her sister. Elena thinks she's crazy, so they go to Stefan together and ask him what he is. Stefan confirms that he's a vampire.
Stefan lingers around their house, hoping that Elena will let him explain. She won't, but Phoebe will. She tells Stefan that she knows he won't hurt her or Elena, and agrees to let him explain whatever he wants tomorrow. Partly for her own curiosity, and also because Elena will listen if she tells her that Stefan is harmless.
September 30, 2009:
Phoebe spends the day with Stefan, learning how he and Damon became vampires.
October 31, 2009:
Stefan is forced to kill Vicki to protect Phoebe.
It breaks Phoebe's heart to have to lie to Matt about his own sister. To spare herself feeling this way again, when she inevitably has to lie to Matt again, she has Damon compel her to believe that Vicki is alive. That she's just run off to keep herself from losing control on those she cares about.
November 30, 2009:
Phoebe figures out that Damon came back to town in the hopes of rescuing Katherine from the tomb, at Stefan's request.
After Emily destroys the pendant needed to open the tomb, and Damon is upset by the thought of never seeing Katherine again, Phoebe sits with him. He may be grieving the loss of another woman, but she's still his friend.
December 2, 2009:
Phoebe asks Damon not to leave Mystic Falls. He agrees to stay for her, but not in so many words.
Phoebe and Damon grow closer during a frightening interrogation by Logan Fell.
Phoebe gets into a bad car wreck on her way back to the Boarding House to get her sister.
December 3, 2009:
Phoebe goes on a roadtrip to Georgia with Damon, after he rescues her from her wreck. They have a good time and bond further.
Phoebe saves Damon's life, when Lexi's boyfriend tries to get revenge for Damon killing her.
December 8, 2009:
Damon gives Phoebe her seashell vervain necklace as a 'thank you' for saving him back in Atlanta.
Damon escorts Phoebe to the decade dance. He compels the DJ to play her favorite song, and they dance to it.
After the dance is over, Damon takes Phoebe for a romantic night out, dancing to old 50s records on a rooftop.
December 12, 2009:
Phoebe convinces everyone that Damon can be reasoned with. That he can be convinced to work with them in a cooperative manner. To their surprise, she succeeds in doing so. He also admits that there's something between them. He doesn't know what, yet, but there is something.
After being heartbroken that Katherine was never in the tomb, Phoebe stays with Damon.
February 6, 2010:
Damon takes Phoebe to meet Agnes and Zoie.
February 7, 2010:
Damon is Phoebe's escort for the Miss Mystic Falls Pageant. She and Caroline are co-winners.
February 14, 2010:
Phoebe gives Stefan an intervention, and convinces him to go on living.
February 15, 2010:
Phoebe met Isobel for the first time. She confirmed Phoebe's long-held suspicion that John was her and Elena's biological father. A theory she formulated when she was only 4, after overhearing an argument between John and Grayson about who should raise Phoebe.
Phoebe discovers that her medical condition – cystic fibrosis – does not come from either side of her family. Though a hereditary condition, it was not inherited. She has a mental breakdown, unable to understand how this was possible. Damon has to compel her to not let it cripple her. To believe that she will find the answers she seeks, one day.
It's revealed that compulsion only works on Phoebe, if she wants it to. She can remember the first time she met Damon, even though he compelled her to forget it. However, when she asked him to compel her to forget that Vicki was dead, it stuck.
February 25, 2010:
Phoebe and Damon have their first kiss. It's also Phoebe's first kiss, ever.
Phoebe gets a hint that she may have powers, when she momentarily takes away Anna's pain.
Phoebe temporarily dies saving Damon from a fire. She's taken to the hospital.