Sharing Your Past in a New Relationship
Question: Should I tell my new girlfriend all of my past?
Answer: Why, is she asking?
My general rule is that if it’s something your collective friend circle knows about you, then your girlfriend ought to share in that knowledge too. The goal is to keep your partner from looking, and eventually feeling, like an ill-informed idiot.
For instance, if everyone attending your best friend's wedding knows that you had a drunken one-night stand with bridesmaid Sally two years ago, you should give your new girlfriend a heads-up at some point. It needn't be now, but it should definitely be before she meets Sally in the wedding buffet line.
The extent to which you go into detail is all on you. Few people need, or even want, the full background story. Feel free to stick to the most basic of information. Should she need more detail, she'll have to ask for it.
If there are skeletons in your closet that you’re wary of sharing, then chances are high that your girlfriend will consider that information relevant. This includes, but is not limited to: corporate fraud, accidental weddings in Vegas and children sired in previous relationships.
Again, timing is key, but such things are best told in advance of her finding out for herself. A story you're able to frame up yourself trumps one spewed out by the grapevine, after all.