QUOTE (Kawasakifan @ Sep 10 2009, 06:24 AM)

Hi
If I recollect correctly, Natalie and Monk have been on only one date in 5 years - it took place, naturally in the Hal episode and seemingly never again.
If we want to give any kind of credence to these characters we could speculate why just one time; perhaps as you said, she felt uncomfortable because Monk is her boss or more simple her feelings just did not extend beyond admiration and pity and being with him after work that one time wasn't that attractive to her so if she does find other employment because Monk doesn't need her services any longer what incentive does she have to continue to see him other than as friends because it seems that the writers have taken great pains to not have them exhibit romantic feelings in either about the other.
KF
This is Liv, I am having issues with my computer and the message board.
I personally wouldn't call that a date, personally.

Not unless that means I have dated my best friend, my sister, my mom, and even a friend of my husband since I got married, and he was aware with all of these dates and was okay with them. Going to take in some kind of entertainment with another person, no matter the gender, marital status or even relationship doesn't really qualify as a date, even if one party buys the other a tee shirt at said event.

But just because I don't think of them going to see 'some kind of animals on ice skates' as a date doesn't mean that you shouldn't, it's a matter of interpretation. But my interpretation that it wasn't a date would eliminate the need to answer why only one time.
If I were a shipper and wanted to see that one time as a date, I suppose I could assume that maybe the fact that they have a working relationship, boss/assistant, made one or both of them feel a bit awkward, and they felt that any further dates while she was his employee were probably not the best of ideas.
Possibly during the course of the evening, he kept thinking of Trudy and realized that he wasn't yet ready to move on, and that it would be unfair to Natalie if he tried and failed. This would have the benefit of being because he was thinking of Natalie's well being and not just his own.
Possibly neither of them was willing to outright call it a date for fear of learning that they had misunderstood the other's intent. And not knowing what the other person is thinking, neither wanted to probe too much and then be embarrassed that they had basically admitted to having feelings for the other that might not be returned. Should that scenario happen, then things would be very awkward between the two of them afterward.
Perhaps over the course of the evening, one or both of them came to the conclusion that even if they both had some potentially romantic feelings for each other, they would be putting quite a bit at risk if they chose to pursue it. If they went forward with it, and the relationship went bad, it would become just about impossible for them to work together as smoothly and easily as they had before. Even if the relationship didn't go bad, but they had minor spats as many couples who are otherwise happy together occasionally do (and I would imagine that Monk, as he is at this point, there would be a lot of these spats and disagreements) that it would interfere with their work, no matter how often they said they wouldn't allow their personal relationship to affect their working relationship. Because if they can't work together, Natalie is out of a job, Monk won't be able to do his job consistently without her, and it would probably be even more difficult for him to find a replacement for her than it was to find a replacement for Sharona, because he hadn't been romantically involved with Sharona, he would warier, like the adage, 'Once bitten twice shy.' And when Sharona left, it took him three months to find Natalie, and then a few months for the two of them to get used to working together and iron out their different perspectives. So taking a chance on a romantic relationship at that point might have seemed like too great a risk for them.
Which brings me back to the interpretation that once he is back on the force, and Natalie is no longer his assistant, the risk of has been somewhat reduced. He is not dependant on her for his job anymore, and vice versa. If they did have a fight, they would each be able to take a break from one another and take a few days to clear their heads without having to be thrown together on the job.
If he gets reinstated and solves Trudy's case, then he is logically making good headway and the point at which he is able to finally let Trudy go and put her memory to rest would be within reach, meaning that he would sooner rather than later be capable of pursuing a new relationship.
This still doesn't mean that I am in favor of a romance between the two of them, I am merely offering examples of how a shipper might choose to interpret this turn of events in a way that isn't upsetting to them, or that they could see as a positive thing. I just want to be able to form my own possible conclusions as well, one where they don't become involved romantically.