There are two ways of looking at this. Holding a secret means " I really should tell them (because its really important). But I can’t/won’t for reason XYZ".
Then there is “I kinda shoulda tell them, but its no big deal, probably doesn’t make any difference, and what is the right time to do so?”.
So, IMO, the time interval itself isnt so much a big deal. The devil’s in the details on this one. Which one is it?
Real-life example: A year or so ago, my wife of 11 years was drinking with her best friend, who casually referenced her and I fooling around some 15 years ago, before my wife had met either one of us. She was fairly upset by the revelation.
Now, I wasn’t intentionally keeping this a secret. I sorta thought she already knew about it, as it’s something I’ve mentioned to more than one person. And it was a long time ago, so it certainly wasn’t any kind of elephant in the room. Hadn’t thought of it in years, in fact. But either she’d never been told, or had forgotten (which would be reasonable if it had come up before she had a reason to care), and it was unnerving to her.
After a little time passed, she was over it. It didn’t affect their friendship or our marriage at all, at least, no more than any other tiff.
This is my reaction too.
I would be surprised. My probably-best-friend is a guy, my husband is obviously a guy, and they’re both straight. Also, they’d have to time travel, because I know they’d never met before I introduced them.
So, yeah, very surprised.
Wow, really? What if his total was 10 times yours–would that have nixed the deal?
As for me…it depends on which of my friends she slept with, and when. A couple of guys I know have herpes.
By default, my reaction is the same as yours. “Why would it matter?”
But many people do seem to have an irrational but understandable possessiveness towards their partner, so I can see why sometimes someone would care, even if I think they normally shouldn’t. For instance, if it was an obvious “they got together, it was fun, they moved on”, then it shouldn’t matter. (Although it’s pretty common for people to find it weird to imagine their partner having sex with other people, even if they actively support each others’ right to have had a personal life before they met.) But conversely, if it seemed likely something was unresolved – if one of them moved away, but they were still in the “could anything serious happen” phase, or one of them was clearly not interested, but the other might have been, I think most people could see why that might make someone uncomfortable.
Similarly, my actual other half and best friend are really nice and get on well, but are quite different, and I really don’t see any attraction between them. But I can imagine other friends and other exes where I might have felt insecure if they were really close – not a rational thing, but a “what are these two people getting from each other they’re not getting from me” thing.
Or, in other words, it might be similar to the question of “would it bother you if your friend had the hots for your other half”? I think most people would feel uncomfortable in that situation, more than just sorry for their friend, but hard to explain exactly why it bothered them.
It’s hard for me to even imagine. I was 34 when I met my wife, and since college, the women I’ve romanced/hit on/whatever have been outside of my circle of friends. So even by the time I met my wife, it had been a long time since a close friend of mine would have had the opportunity to have known a GF of mine before I did.
Back in high school and college, when I usually was pursuing girls who were part of my social circle(s), the possibility that a friend of mine might’ve shared some passionate moments with them first was simply a reality, and if it had turned out to be the case it wouldn’t have been a big deal. But I was having so little romantic success back then that it was pretty much a moot point.
Oh, I just saw that movie, too!
In the film, the reason it didn’t come out earlier was that the two guys became friends in college around the time it happened, and friend A, who had slept with her before B started dating her, agreed not to say anything about it because the girl was into his friend B & she didn’t want to sabotage things when she and B were first dating.
It later came out when she was holding it over A’s head as blackmail.
And B’s response was anger over not having been told about it.
Looking at this as a pure hypothetical, I can see a reason the friend might not tell, but not the SO. It obviously isn’t unimportant to her, or it would have just come out whenever we and the friend were just hanging out. And if it’s so important to keep secret, I have to wonder why. Surely, by the time we were in an actual relationship, she would know that the fact that it happened wouldn’t bug me.
The friend could think it’s just something the SO should tell.
So single women should be waiting primly on the off chance that they might meet you?
And then guys complain that they marry women who don’t like sex…
We have a winner!! 
It wouldn’t bother me.