In Mother and Child Reunion (1), Caitlin is talking to Keith on her cellphone while she is heading to her high school reunion as she is looking at her engagement ring. She tells all of her old friends about Keith and how they are they getting married. Later, at a bar, Caitlin introduces her friends to Keith. After seeing Joey Jeremiah's car sales commercial, Keith starts criticizing it and tells Joey to lose the car salesman vibe. Caitlin remarks that Joey was a total ham during high school to Keith and says that he is the same old Joey, which upsets him. It is revealed that none of Caitlin's friends like Keith and believes that she can do much better.
In Mother and Child Reunion (2), at the reunion, Joey overhears Keith talking to Allison Hunter about how he does not want to marry Caitlin and he and Allison start to flirt with each other. Later, while Caitlin is making her speech, Joey confronts Keith and they start getting into a fight with each other. Joey then makes Allison tell the truth to Caitlin and Allison reveals the truth to Caitlin. Caitlin asks Keith "You don't want to marry me, Keith?" and then breaks up with him.
In Holiday (1), Caitlin mentions Keith by saying that she doesn't date men in "the biz" anymore.
- None of Caitlin's friends liked Keith.
- Keith gave Caitlin money to buy herself an engagement ring.
- Keith did not want to marry Caitlin.
- Prior to her relationship with Keith, Caitlin never had a relationship which lasted more than a few months.
- Start Up: Before Mother and Child Reunion (1) (DTNG 101)
- Broke Up: Mother and Child Reunion (2) (DTNG 102)
- Reason: Keith felt that Caitlin was pushing marriage. She broke up with him after Joey exposed Keith's marriage doubts.