I am not sure whether to write about my "best" relationship (in terms of strength and depth), or my "most compatible" relationship (in terms of chemistry and complementary personalities). I'll do both.
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It's weird because this didn't last too long (due to circumstances), but I think I was most compatible with the 5 (I *think* 5w4). He was just so witty, so perceptive, and really... so BRILLIANT. I was attracted to his reserved and thoughtful exterior, and when he let me into his world, I just picked up on so much depth and sensitivity. We could talk about so many things because he had a lot of knowledge about topics that interested me (we shared the same major at the time), and he seemed to have endlessly entertaining or thought-provoking insight about things. Our perspectives were often similar but complementary. I found him pretty grounding. He is an INTP btw.
I think we were both pretty dark and sensual people.
I do wonder how things might have gone under different circumstances, because I know it's easy to idealize young love that ended while still in the honeymoon phase, but I miss him and he's the only one I'd like another chance with.
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Okay... well, my longest and most serious relationship was with a 1w2 (INTJ). It worked for five years and we almost got married, but no, it didn't last. He was incredibly supportive, sweet, HONEST, sincere, intelligent and analytic. I was attracted to his strong moral reasoning, his willpower, and his authenticity. He was super responsive to me, and completely validating of my feelings in most cases.
However, why didn't it work? Well, for one thing. I'm pretty sure he had an undiagnosed mood disorder that he refused to get help for. I felt like he was overly critical of me in a lot of ways, and I started to feel like I couldn't do anything right and I barely had any room to breathe the way I wanted to. He wasn't abusive or anything, just very perfectionistic about things I found inconsequential. It was draining. I found him uptight as well; I have a pretty dark and often crude humor, which he didn't share. He would take everything so SERIOUSLY and I just started feeling derailed all the time. By the end, I never laughed. Of course this is just my side of things, but I also am pretty sure I couldn't give him what he needed or expected either anymore. I'm way too disorganized and overly sensitive...
But he's still one of the best people I've ever known. I love him and miss him in ways. We broke up last December (2012). I didn't really start learning about enneagram until right around the time we broke up, but honestly I can't see myself ever dating another One lol. Maybe it's just too soon.