"I'm not stupid, okay? I know you still have feelings for Joe, and I get it, he's amazing. But here's what I also know: Joe and this family - they need me. Not some charming, klutzy, fun-and-games blast from the past. Me."
When Caitlin returned, she still had feelings for her former flame, Joey Jeremiah. However, he was now dating Sydney, which disappointed Caitlin. Sydney easily figured out about Caitlin's remaining feelings, and confronted her about them, saying that Joey and his kids needed her, not a "blast from the past". Caitlin was upset about this, and when Joey heard about the fact that Sydney told her off, he realized he still had feelings for Caitlin and broke up with Sydney. Caitlin and Joey then decided to get back together.
In Father Figure, while attending Spike's baby shower, Caitlin accidentally sat on a piece of cake and Sydney goes over to help her. Caitlin introduces herself as an old friend of Spike's and assumes that Sydney must know Joey as well. She mentions to Sydney that she and Joey dated then jokes that she and Joey will get back together. Joey comes over and kisses Sydney. Caitlin then realizes that Sydney is Joey's new girlfriend and then becomes embarrassed of what she just said. She says to Sydney that it was nice meeting her and then walks away.
In Holiday, Caitlin becomes jealous of Joey and Sydney's relationship but still she wanted Joey to be happy. While babysitting Angie, she allows Angie to wear the costume that Sydney made for her though she ends up getting it dirty. When Joey and Sydney return home and Sydney sees Angie's costume dirty, Caitlin tells Sydney not to be mad at Angie but Sydney says that she's not mad at Angie and glares at Caitlin. After Caitlin kisses Joey, she goes to Spike for advise on what to do. Spike tells Caitlin to write her feelings on a letter and give it to Joey. When Caitlin puts her letter in Joey's slot, she then tries to go back for it but can't reach it. She tries to get inside the house through the window but gets stuck. Joey and Sydney return home and find Caitlin stuck in the window. After helping her get out, Sydney then talks to Caitlin alone. She tells Caitlin that she knows that she still has feelings for Joey but then tells her that Joey and his family only need her, not Caitlin. She then calls Caitlin a klutz blast from the past. However, Craig overhead Sydney talking to Caitlin and found Caitlin's letter. Caitlin then grabs her letter from Craig and runs out. She then starts ripping her letter and starts crying. Craig later tells Joey of what Sydney said to Caitlin and Joey confronts her. Joey asks Sydney why would she try to make Caitlin go away. Sydney explains and then asks Joey if he loves her more than Caitlin. Joey doesn't answer and looks down. Sydney gets the message and then leaves. Joey later gets back together with Caitlin.
In Time Stands Still (2), when Joey decides to sell his house for sale because of his financial trouble, Craig calls Sydney since she's a real estate agent. When Caitlin learns that Sydney is selling Joey's house, she goes over to Syndey's office and decides to buy Joey's house. This gives closure between the two women.
- Both of them dated Joey.
- Both of them acted as a mother figure to Joey's daughter Angela Jeremiah.
- Joey cheated on Sydney with Caitlin.