Kyle is Juliet's date at a bowling alley during "He Loves Me, He Loves Me Not, He Loves Me, Oops He's Dead!". Shawn happens to be at the same alley for an investigation, and has Juliet introduce him to Kyle. Kyle thinks Shawn's job as a psychic is pretty cool and asks him to predict his future, and as Shawn is uncomfortable seeing Juliet date anyone but himself he predicts Kyle will face rejection. Juliet understands what Shawn is getting at, but Kyle has no clue what he is talking about.
Juliet later tells Shawn she had to break up with Kyle because he is a bad bowler, a dealbreaker for her. Shawn is obviously pleased to hear this, but does a good job hiding it.