Boyfriend was a friend first, so she knows all his gory details
Q: I'm madly in love with my caring, funny and stable boyfriend of over a year. We've been relatively drama-free, despite being long-distance the entire time. We were good friends before dating, so knew quite a bit about each other going into it, skeletons included. There's no doubt that without the foundation of friendship, our relationship would not be as strong as it is.
But I've had issues in the past year assimilating some of the information I learned as a "friend" in my current role as the "girlfriend" — e.g., a good friend he referred to once as "the one who got away" in a night of drinking pre-dating, whom he's currently visiting in another town. Or information about our dating histories that we might have otherwise sugarcoated in retelling a significant other, but shared gory details with since we were pals.
To be clear, it's not jealousy I wrestle with; it's more information overload. I think he sometimes forgets I know as much as I do because he tells me the whitewashed versions of stories I've already heard, and I mentally fill in (and then obsess over) the details he left out. Is it odd that I almost wish I knew less?
Blissful(ish) but not ignorant
A: No, but I don't think less knowledge is what you need, especially since you (I think rightly) cite your gory-details friendship as a source of your relationship's strength. If anything, you need other, complementary stuff out in the open.
First, tell your boyfriend when he's sugarcoating a truth you've already heard. "Er, (Boyfriend)? Remember, I've already heard that story. Unabridged."
Next, ask for more information on the stuff that doesn't sit right. For example, if his visiting "the one who got away" bugs you, then you need to tell him that you want to be the cool girlfriend and high-five this friendship, but you can't shake the memory of his drunken pining for her. It's not either-or, silent sufferer or jealous harpy.
About that pining — in vino veritas, yes, but there's also sentimentality in vino, as well as a real risk of driving into trees. So if he's plainly devoted to you, feel free to consider his "one who got away" speech a moment, not a mission. End of side note.
The next bit of information I think you'll want to add: what it's like for you to be together, together. As in, not long-distance.
Close friends who become a couple will have the goods (or more appropriately, bads) on each other. That's just how it works. But what they create together as a couple displaces these stories and pushes them toward the horizon of the past; the start of their romantic relationship becomes the line that defines "now," and those gory details become "then."
Your being apart slows down the process of creating a "now" — and, in a much less high-concept way, also delays your getting to know each other better, developing trust, growing closer.
It's not the mark of relationship doom, and presumably you'd be together if you could. It just means it's going to take you a little longer than it does other couples for your stories together to displace the relationship ghost stories you told each other as friends.