The Lily-Jeffery History

Lily and Jeffery first meet in Judgement Day when Lily comes storming into Jeffery's office.  She's pissed off at the warrant he issued to Woody for the arrest of a distraught mother.  Later in the episode Lily and Jeffery are held hostage together.  While nothing happens between them, there is an understanding and a friendship that starts to form between them.

Total Recall brings Jeffery to the morgue to work on a case with Jordan.  This leads to a some further interaction between Lily and Jeffery.  Jeffery comes by Lily's office at the end of the episode.  He uses the excuse that he was stopping by to let her know who won the little wager (going on at the courthouse over the case Jordan was working on).  It's obvious Jeffery wanted a reason to see Lily and was trying to ask her out.  He however chickens out.  Lily even tells Jeffery that she was about to take a break for lunch.  She stands up expecting him to ask her out and instead he chickens out and slams her office door in her face as he makes a hasty retreat.

In Death Goes On Jeffery tries to talk to Jordan about Lily.  He wants to ask her out.  When Jordan finally realizes that Jeffery is asking her if he stands a chance with Lily Jordan tells him he's 'not the right person' for Lily.  This doesn't deter Jeffery. 

Jeffery doesn't give up though.  He goes to Garret and tries to talk to him.  He's nervous and stuttering.  Garret tells him to sit down and breath, then gives him a drink.  Not a good idea--Jeffery can't hold his liquor.  He then runs into Lily in the break room.  She realizes he's drunk and gets mad at him.

Finally at the end of the episode (a sober Jeffery this time) stops the elevator doors from closing and jumps in with Lily.  He tries once more to ask Lily out.  Lily finally puts him out of his misery and asks him out instead.

Elephant in the Room proves things are going well between Jeffery and Lily as they have small talk on the phone and we see Lily laughing.  Obviously the first big obstacle has been successfully jumped.

In Thin Ice things appeared to be moving along between Lily and Jeffery.  It even seems Lily's judgement has been lost when she yells at Jordan for impeding Jeffery's case.

Things get iffy in Mysterious Ways when Lily sees Jeffery with another woman.  She thinks he's seeing someone else.  Then Jeffery admits it was his mother he was with.  Lily wants to know why he was hiding this from her and why he won't introduce them.  He's afraid.  He comes from a Jewish family--Lily's not Jewish.  Plus he's a 'mama's boy'. 

Lily has an interesting lunch with Jeffery's mother.  The result of this lunch is Jeffery asking Lily to marry him.  When he pops the question Lily is stunned, but she says yes.  She says yes a couple of times, repeating herself--almost as if she is trying to convince herself that this is what she wants.

In Mace vs. Scalpel Lily is planning her wedding and having second thoughts.  She claims that Jeffery asked her and he deserved a response so she had to tell him something.  This while she is out with Bug, who is supposed to be meeting his date--Amy.

Lily is jealous when she realizes that Bug was supposed to be on a date. 

In Don't Leave Me This Way Lily questions whether she wants to go through with this wedding.  She's trying to deal with Jordan and the murder of JD.  She finally calls off the wedding as she's supposed to be walking down the aisle.