MJ, your H is at the dysfunctional end of the 4 spectrum. When I get into one of those 4 funks I hate myself and feel embarrassed even while I can't get out of it. So that's another reason why you should empathize from a distance. Let him deal with it on his own-- it's not about you-- it's an existential angst that you can't cure. To focus on it not only doesn't fix it, it embarrasses him further and permits him to dig in deeper. I'm relieved when my bf doesn't focus on my mood but just seems understanding from a distance.
And get this: he wouldn't be happier with any other kind of woman either. Really. His unhappiness comes from inside of HIM, but he is too dysfunctional to see this, so he will ultimately blame his unhappiness on whomever he's with, including Ione Skye, okay? It's not you.
I'm a 4 who has been in at least FIVE long term (defined as 3+ years) relationships (plus having had seven other shorter-term lovers AND I was a virgin until age 21), and I can tell you that I keep having the same problems with and same complaints about my partners over and over again. After 30+ years of therapy, I've finally figured out that it's ME not THEM.
Let this sink into your psyche, honey-- it's not you. He is at the dysfunctional end of the 4 spectrum!
Re the 5-- I think you're missing the point on the 5. The 5 may or may not be frumpy or dowdy or shy. The key characteristic of the 5 is that s/he is the SCIENTIST. The 5 thinks that the world can be made to make sense with more information, knowledge, investigation, objectivity, order. Think table of elements, or classification of plants and animals. The 5 wants to sort things out and make sense of them. She can do this while dressed in gray sweats at the library, or while wearing a sequined miniskirt at a bar.
This is how one of my Enneagram books describes what it looks like when the 7 moves toward the positive side of 5:
-They become quieter and more introspective and objective -They explore subjects in depth and place more value on wisdom and self-discipline -They become more accepting of both polarities of life: good and bad, happy and sad -They become more serious and are taken more seriously -They get in tough with their fears
[This is very much in keeping with your FlyLady approach to housework, for instance.]
When 7's move toward the negative side of 5
-They push their theories onto people -They become more self-absorbed and escape responsibilities.
Note on sources: Are you working with any Enneagram books or just using the tidbits we've discussed on this site, or the Enneagram Institute site? The Enneagram is a huge and very fertile system of thought. A quick book for an overview is The Enneagram Made Easy by Baron and Wagele. Suggest you get this one and use it for quick reference. A much deeper one (that's out of print) is The Enneagram of Liberation by Eli Jaxon-Bear. A good middle one is by Riso and Hudson... it's called The Wisdom of the Enneagram (I think-- it's lost somewhere here in my office-- it's a large blue paperback). Later books by Riso and Hudson are good. Early ones by them are not so good and avoid anything by Riso alone-- poorly written and poorly edited.