The Lily-Bug History

In the first season we had a sort of love triangle going on.  Lily liked Garret, Bug liked Lily and Garret was oblivious to it all (until Jordan opened his eyes).

In Bomb’s Away Bug finally works up the courage to ask Lily out but Lily turns him down.  She tells him he’s sweet but she just considers him a ‘good friend’.  He’s still secretly mooning over her.

In Don’t Look Back Bug pretends to be Lily’s fiancée when her mother comes and visits.  He’s sweet, loving and acts like a perfect fiancée.  Only he’s not acting, Bug really cares (still).  Lily’s mom tells Lily not to let Bug get away (after she realizes what’s going on) cause there’s one thing she knows and it’s men and that man (referring to Bug) loves Lily and she could do a lot worse.  Lily doesn’t respond to this comment.

In John Doe Lily and Bug have another moment in Bug’s apartment.  There seems to be a connection between them.  Then in Fire and Ice Lily and Bug are at Fenway (to spread the ashes of a man who’s case they worked on together) alone.  There’s a moment were they connect again and there’s the feeling that they might suddenly try something then they’re interrupted and that’s the end of any possible budding romance.

Bug seems to have become content to just be Lily’s friend now.  Though every now and then Bug does something sweet and extra caring for Lily.

Season Five sees the rebirth of Lily and Bug.  While it's always been known that Bug harbors feelings for Lily, it never seemed Lily returned them.  The green bug (jealousy) starts to show itself throughout the fifth season however. 

Lily meets Jeffery Brandau in Judgement Day.  Sparks fly (not necessarily good sparks).  When Lily starts dating Jeffery, Bug gets upset.  He thinks she can do better than Jeffery.  He battles with his feelings and finally in The Elephant in the Room he tells Lily exactly how he feels.  He leaves the ball in her court.  She does nothing.  She even gets so far as accepting Jeffery's proposal.  When Bug goes out on a date with Amy (Mace vs. Scalpel) she's visibly jealous.  Still she does nothing.  It's as if she's waiting for Bug to come riding in again and claim her as his.

When he doesn't do this she finally has to admit that it's up to her to take the next step.  In Don't Leave Me This Way she calls off her wedding (practically at the alter).  Then goes in search of Bug.  For the first time Lily and Bug are giving a relationship a true shot.