Mutually Exclusive: The one I thought was The One is now the only one who won't be friends

Dear Carolyn:
I'm getting married this 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 right now, 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 point of fact, Annie is/was friends with most of her past boyfriends (including an ex-fiance). Her not speaking with me, even though she has my contact info, 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

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 "nearly all" and "most of" their exes, respectively. 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.

Yikes--more people who just can't let go. At least he's not lamenting that she hasn't accepted his Facebook friendship! I think Carolyn totally nailed this guy's hang up: he doesn't want to be someone's worst memory. Although by calling repeatedly, he's only cementing himself as her "crazy ex"--in her mind and her husband's.

Speaking of which, the only reason that I can see that after years he suddenly feels compelled to make contact is his impending marriage. It seems he wants to "resolve" this issue before entering this new phase of his life. What he doesn't seem to notice is that she's already been there, done that. He doesn't say whether three years ago she called him as her own transitional soul-purging or whether he contacted her when he heard she was married. But in any case, she's clearly moved on--and considering she has not one but two ex-fiances, it's probably a good sign that she's showing commitment to her actual marriage, and not the potential ones that never came to be.

It's really, really, really OK for things to end, for people to move on! When we say "let's be friends," I think that MOST of the time we really mean one of two things:

1) "I'm so used to having you in my life that even though I don't want a relationship with you, I'm not ready to cut the apron strings"

2) "You're not a bad person and I wish you well in your future life. Though I don't actually care to be a part of it."

and very rarely

3) "I love you so dearly as a friend that I misinterpreted my feelings as something else, and now that we've moved our relationship that direction, I realize I was mistaken. I wish we could go back to the way things were, even though I know that's impossible." But I would contend that if you've gotten to the point of a (broken) engagement, this one's no longer viable

Speaking once in six years doesn't exactly speak to a deep desire to cultivate a friendship. Even if they got back in touch, I think he'd be surprised to find she's probably very different person than the woman he loved probably close to a decade ago, before their relationship went sour.

I wonder if this guy's current fiancee is encouraging him to make amends and peace and move forward, or if she's annoyed by or concerned about his obsession, or if, worst of all, she has no idea about it. It's a LITTLE odd, isn't it, that he doesn't have a single thing to say about her, except he knows she's friends with most of her exes--suggesting that he's comparing the two of them to each other, and even sought the new fiancee's input on why the old one won't talk to him. Really? That's a little strange.

Also, the ex "apologized voluntarily"? As opposed to what? The involuntary relationship he's trying to coerce her into now? I wonder what he has been doing in the intervening years, on this "long personal journey," and why it seems like it just took him in a giant circle?

And in conclusion, I am skeptical of people who say "autumn" in print when they would almost certainly say "fall" in conversation. Minus 2 points for pretension!