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el_staplador asked about a decision I was pleased I made.
This made me think about dating D for five years. We were both post-college; he was post-grad-school for almost the entire relationship. Four of those years were in a medium-distance relationship (we were about 100 miles apart and saw each other almost every weekend, but rarely during the week). We did not live together for any part of those five years. We were clear that we were both interested in marriage as a long-term plan. I wanted to get married, or at least engaged, for a good part of those five yeras, but D maintained it would be rushing into things.
General wisdom is that if a guy (or girl, for that matter) is taking that long to declare himself (given, of course, that marriage is an important thing for both of you), maybe He Just Isn't That Into You. Or if you look at any advice column/board, the overwhelming advice would be to Dump Him Already. Or if you asked my parents, they wondered if he was really into me as well, often fairly vocally.
We're coming up on eight years married now, and my life is immeasurably more wonderful than it would be without him.
In this case, D was right that we should not have gotten engaged while in a medium-distance relationship, as we really needed to figure out how to live in the same general area. Also, and more to the point, D's personality is such that he just really, really doesn't like making decisions. (Exhibit A: the car we've been planning to buy. Since I really don't care what car we have, and he does, the decision has been up to him. ...Five years and counting.) It wasn't that he didn't want to marry me, it was that he wanted to give the question the weight he thought it deserved. In fact, he still jokes that we rushed into marriage :)
The decision I'm pleased about wasn't to keep dating D, or to eventually marry him (although I'm of course extremely pleased about those too, it's not what I'm thinking about right now): it was to trust him, and trust myself that I understood him, in the face of a lot of messages that were, sometimes subtly, sometimes not-so-subtly, telling me otherwise.
...My sister, on the other hand, was in an almost-three-year relationship that fit the same profile pretty much exactly, and it turned out that in fact he really wasn't that into getting married to her and the optimal solution was to break up. (They're now both happily married to other people.)
So I'm not sure what the moral is? :) I think it is... to listen to myself, whether my self agrees with or disagrees with conventional wisdom. I tend to worry a lot about what society says My Life Ought To Be Like, or to try to conform to what I hear around me stated as This Path Will Lead to Happiness. I'm glad that I got past that, in this case.