The problem isn't her silence, it's his refusing to accept it
Q: I'm getting married in autumn. My life is great after a long personal journey, including one broken engagement. My only problem is that my ex-fiancee, "Annie," is incommunicado with me, which really bothers me.
I'm friends with nearly all of my former girlfriends. Likewise, my fiancee is friends with nearly all of her exes, many of whom I've met. In fact, Annie is/was friends with most of her past boyfriends (including an ex-fiance). Her not speaking with me seems out of character.
I've spoken with Annie only once in the six years since we split. That was three years ago, when she was recently married. She sounded fine, too. Our relationship ended on a sour note, but last time we spoke she apologized voluntarily for the part she'd played in that. As did I for my part.
I've tried calling her, maybe four or five times, over the past couple of months. Annie won't answer or return my calls.
I'd like to make some peace and see if we can't cultivate a friendship. At what point do you give up on somebody? Am I unreasonable to pursue her friendship?
Wondering in Seattle
A: Four or five unreturned calls in two months are two or three unreturned calls past the point when you give up.
As for how reasonable your effort was, that depends. If you were motivated by missing Annie's friendship, then that was reasonable. Still futile, at this point, but reasonable when you first had the idea. If you're motivated by pining or what-ifs, then it's reasonable to be concerned — about your current, not ex-, fiancee.
If you're motivated, however, by a desire to remove the one blemish on your record of amicable breakups, then the reasonable choice would have been to nip the impulse in the bud.
You and Annie parted on a sour note, and so you're stuck with this: There is someone out there for whom you conjure painful memories, someone who thinks her life is better without you, who has declined your friendship, apologies notwithstanding (they're past anyway, not prologue).
It's not the kind of news anyone wants to hear, but we all have people out there who don't like us or don't remember us well. It's a natural, unavoidable byproduct of having a personality, opinions, a soul.
That you apparently have just one Annie is, in fact, exceptional; even you point out that Annie and your fiancee are friends with "most of " and "nearly all" their exes. As in, not every one.
So maybe your "only problem" isn't Annie's silence; it's that you won't accept that you made "some peace" three years ago. Unless you're pining (see above), please content yourself with that voluntary, all-is-forgiven, perfectly fitting goodbye.
She's over him, but how could he move on to someone else?
Q: If I'm over my ex, how come it hurts so much to find out he's dating someone new?
What's Wrong With Me
A: Knowing we can't be right for everyone sounds fine; envisioning him looking That Way at someone else feels awful. Getting over someone is just a lot easier than getting over ourselves — the latter forces us to make peace with where, and who, we are.