The problem is that I can't see Jimmy agreeing to this. He should have a fair idea of what awaits him. Cat would definitely rush out of the place the were meeting. And that would be more embarrassing for Jimmy than for Cat.
But what about this: Lois and Clark stage a row, and Lois tells Clark to look for a date on the internet. Clark tells her that he is doing exactly that, somehow letting Cat know where Clark is 'looking'. Online, Clark agrees to a 'blind date' with Cat, and they agree on some signs to recognize each other (red rose for each of them?) - just that he isn't going to turn up. First Perry comes along (with a red rose) and makes some comments about blind dates, when Perry is gone, Jimmy arrives bearing a red rose and stays for a while, then Ralph, then Lois walks by - bearing a red rose. Finally Clark comes in - and walks directly towards Lois with her red rose...
