dear Matt, thanks for coming back to us.
I am rather worried about your post, but from what I realise is that being "socially awkward" than anxious' is really on a par, because your socially awkward because you are anxious, however what does concern me is what you are actually doing at the moment.
I too wouldn't be too happy if my wife started using a dating service, as I would take this as an insult, and why so quickly.
Denial is a real problem, but I'm not too sure that you are still in it, maybe I'm wrong, but your comment 'unless estate planning counts', plus planning a pre-paid funeral, which then may throw it the other way, because you are laughing at the dark moments, however your lost interest in exercising and having trouble getting out of bed, so the final decision you are in depression.
I know that your professional help hasn't worked for you, but it takes a few times to find the one that you can connect with, so I do urge you to try again, and you can start by looking up 'get support' at the top of the page, and I am also concerned about any medication which you haven't mentioned.
Can I ask you how long you were married for, as I can see this to be a problem that you are trying to overcome. Geoff.