@existential potential,
EP,
I am neither shrink nor detective, but the complex syntax of your sentences and your agile use of metaphor suggests to me that your mind is still very much alive. If one's mind is alive and, most importantly, one keeps moving, so as to increase exposure to a variety of novel experience, one is apt to find the engagement with the world that you seek. While doing this, on another channel, you can be recalling the activities that brought you connection in the past; one or more may have been left dormant long enough that they have potential for new linkages. Calamity Jane's idea of volunteer work is a really good one. One encounters new people, and helping others is usually an engaging process (that typically provides the bonus of making one feel good). The better you feel about yourself, the greater the texture the world will have for you; and more texture means more chances for linkage and engagement.
I can empathize with your boredom; I spend a significant amount of time scanning for possible connections with the world that will keep it at bay--and always have. May I suggest that you don't want sympathy, for people who sympathize with your boredom will keep you from fully owning the issue and getting into the motion that will help you dispel it and keep dispelling it.
You mention "gloom." If you think you might be suffering from depression, I strongly suggest that you take care of that issue first (with prescribed medication AND talk therapy. By the way, some therapists are stimulating conversationalists). It may well be that, even after the gloom is driven away, you may still be bored, but, if you're not gloomy, you'll see the world and its opportunities more clearly.
Get yourself in motion, NOW. Good luck to you.