I have had a similar issue that keeps creeping up on me also, once paired can't connect. I may not have an immediate answer, but others will need more information to assist here.
As I understand it, there are three flavors of the WebIDE and I also find this a bit confusing.
This link indicates to use the native flavor, which is what appears may be the one you are using.
On my PC this variant allowed the 'Web Bluetooth' connection modal dialog to appear, not 'Com1' 'Com2'. But I am using a BT dongle. Not sure if that matters.
See if the online variant renders a different connection dialog.
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Thr 2018.08.02
Hello @Terrence7
I have had a similar issue that keeps creeping up on me also, once paired can't connect. I may not have an immediate answer, but others will need more information to assist here.
As I understand it, there are three flavors of the WebIDE and I also find this a bit confusing.
This link indicates to use the native flavor, which is what appears may be the one you are using.
http://www.espruino.com/Quick+Start+BLE#windows
On Windows10 this is the nw.exe file found in (on my PC) C:\Program Files\EspruinoIDE
but, . . . . that didn't render the correct connection list, as I believe this is what you are not seeing either.
I then tried this flavor:
http://www.espruino.com/Web+IDE
https://www.espruino.com/ide/
On my PC this variant allowed the 'Web Bluetooth' connection modal dialog to appear, not 'Com1' 'Com2'. But I am using a BT dongle. Not sure if that matters.
See if the online variant renders a different connection dialog.
Other than that, have had trouble with getting the Chrome variant running.
Version 68.0.3440.84
http://forum.espruino.com/conversations/315493/
So, hopefully with your response to this suggestion, others may be able to pin-point what is going on.