Some close to three years ago (2008) I asked my boyfriend out, knowing he was older than me (by 8 years, which isn't too much to me). This has never been an issue for me, I tend to mostly relate to older friends. I know he's got his own relationship history, ect ect. I have my own, though I tend to only date long term, so there wasn't as much to it. I seem to be only his second over one year relationship. Albeit, I facepalm every time he starts up with the "I'm old" "I have baggage" ordeal when he's barely in his thirties.
When I first started dating him, I looked up his name, variants of the name, and his known online aliases (in my experience, most people stick with a certain name for a long time). Unless you like technical jargon forums, the only things of interest where his poetry, a couple of gaming/social/journal websites, and his Literotica, for which I could care less what he favorites. Sort of a personal background check. Boring, didn't look into it much.
However, he's going for a T.S. security clearance at the moment, and although I mentioned it before, he finally understood what I meant by the fact he had to give them his personal email addresses, which happen to have these aliases as the default "names" that it sends from. Being a bit of a search engine master, he asked me to spot any of the immediate difficult ones and we fairly quickly got rid of his various old webstuff that while not ing, were a little too full of lovesick poems or favorited erotic fiction to have your potential serious gov't boss browsing through.
And here I hit a snag. One of the online journals mentions waiting for a fiance (probably meant two ee's, though he rarely misspells things) to get home at four AM, written about six years ago. Ok, fine, I know he had at least one long term relationship with a girlfriend end up very very badly, but he never mentioned that part to me. It's not something I've pushed for nor do I blame him for not talking about it, but it does bother me that I had to find out online. I did point it out to him, and his only response was "That was a long time ago". Ok, fine, I know he's not hiding a marriage or anything like my own parents seem to think he is, but that information could have been useful in getting them to drop that. They've been stuck on the idea for a while, had I had that sort of info, it would have saved me a lot of grief between my parents, myself, and my boyfriend, but instead after dealing with their nagging for two years. They could have understood the fact that we are not rushing anywhere because of a past hurt if that sort of information was available to me. It is really obvious I was never intended to find this information.
Privately, he's told me he thinks that marriage is a stupid institution set up to simply give people rules (but also complains how several of his previous girlfriends cheated and/or left him for his friends). Personally, the whole ceremonial thing is too much for me, but having the legal system security in place for financial needs and/or hospital rights, for the idea of partnership, and for being confident enough to state "this is my partner, rawr" are all things that I would be happy to participate in.
I would love to sit down with him and figure out what he expects from me and what I expect from him in this relationship, but at the moment, I am waiting for the post-graduation and just got a new job stresses to fade.
Anyways, TL;DR, Would anyone else be at least a bit hurt to have found out about their long term dating partner's previous engagement (even if it did not result in marriage) via the internet? Even if this isn't something that would affect your relationship if they just bothered to tell you and you wouldn't have pushed about after knowing anyways?
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