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Relationships, like anything else, are a skill. For some folks it's innate, for others it's a challenge. Even "people" persons need to put energy and work into a relationship to sustain it and help it grow and mature.
"Dwight" might just be the kind of person that's relatively comfortable alone, or has some very difficult to fulfill 'ideal partner' concept. If he's chugging along as-is, being happy, fine. If he's seeing not being attached as a major issue, and obsessing over it is causing him other problems in his work or personal life, then yeah, maybe some kind of intervention is warranted.
Your friend may or may not be gay. My gaydar's pretty good, but unless I'd get a face to face (not likely) I'm not even going to guess. But either way, he's your friend, and that's really what's important at the root of it all, yes?
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