text: Q:
  
  Disclosing my past relationships to my girlfriend
  
  My girlfriend and I are both in our early 20's in the US. We have been together for almost 3 years and have been living together for a few months now.
  While I've been with other girls before her, I am her first for everything. First kiss, first boyfriend, first everything. This has been a sore point for her and though I don't consider it a big deal, I know that it's something she dwells on. We've had many long conversations about it in which I try to emphasize that I'm not with those people anymore, I'm with her now because I love her now. However, while she may put it out of her mind for a time, I know it's something she always comes back to.
  Early in the relationship, maybe two years ago, we had a conversation about my past relationships where she wanted to know who I had been with and what we'd done. Knowing already about her insecurities with my past relationships, I withheld some of what I did. I told her about all the girls, but I specifically told her I only kissed a girl I in fact slept with (this would be a big deal as outside of my girlfriend I'd only slept with two other girls).
  I know this was wrong and whatever pain I was trying to shield her from will only worse now when she finds out. It was honestly probably mostly selfish of me to withhold the information anyways. But it's something that's been eating at me all these years.
  We just had another conversation about my past the other day, and I was forced to continue the act. I really love this girl and I don't want to continue hiding things from her, even if they happened years and years ago.
  How can I come clean about my past and tell her how much actually happened in a way that will minimize both her mistrust of me and her self-consciousness?
  (Note: I'm completely open to a frame challenge that argues against telling her at all, but as I'm pretty set on telling her, it would have to be a very strong argument) 
  
  A:
  
  I've been married for over 20 years and have discovered a couple of things.
  
  She's always going to find out
  It's better if you tell her
  You both have pasts that you have no control over
  
  A lot of this depends on the strength of your relationship.  If it's still fragile, then you've got a whole different issue going on after 2 years.  But let's say things are going well.
  I'd suggest picking a time when you both don't have a lot of other things going on.  So don't do this at a family gathering, holiday, or important event.  Take an evening when you both are calm and not in the middle of some other discussion.  Then, lay it out.  "There's something I haven't told you.  My thought process was this..." and explain WHY you chose to not tell her.  Take responsibility for your decision and apologize, and then lay out what you should have told her.  I've found that just telling her works better than getting into a long explanation: tell her what you have held back, give a short explanation why, and then apologize for messing up.  
  It's important to tell her everything you held back at this discussion. If you tell her more later, she'll question whether there's other stuff you haven't told her.  That can be... damaging to your relationship.
  
  A:
  
  Your only mistake was lying about things when asked the first time... 
  It may be an unpopular opinion, but you still have a right to privacy in a romantic relationship. Your past is your past, and you shouldn't be coerced into divulging intimate details that you aren't comfortable sharing. It's one thing to get to know someone, it's something else when they're grilling you for information that they'll hold against you later.
  It sounds like these questions are coming from a place of insecurity, which is a red flag on it's own. If she "needs" to know all the intimate details of your previous relationships for any other reason than simply getting to know you better, it's perhaps a sign that she's not really ready for an adult relationship. As you get older, it should probably be expected that your partner has dated other people before you. Thinking less of them, or constantly questioning how you measure up, is a strong indicator of immaturity and self esteem issues. 
  Your initial response could have been something more along the lines of:
  
  I don't kiss and tell.
  
  Or:
  
  The past is the past, I'd rather not discuss my failed relationships.
  
  Or, perhaps ideally, you could have unapologetically laid your past out on the table. If she could accept your past relationships as just more background information about you, then great; if she couldn't it would have been better to move on early.
  But.... That ship has already sailed. So, if you really want to continue the relationship with this person you'll likely need to come clean. Not because she has a right to know any of it, but because you made the mistake of lying about it.
  Your best bet will probably be to focus on apologizing for the lies. Your mistake wasn't the previous relationship, it was lying about it. Like any apology, admit what you did wrong, accept responsibility, and be prepared to accept the consequences. 
  Try not to excuse yourself with things like "I wasn't honest because..." Or "I was just trying to protect you" Having a reason for your actions isn't the same as having an excuse. You had reasons, but they're not great reasons, and they're not going to make the lies feel better. And I suspect if we're being honest, you lied to protect yourself as much as you lied to protect her.
  Basically, you screwed up. Now it's time to admit it, apologize, accept that she's going to be hurt and angry, and see whether this current relationship is going to be salvageable. 
  If you find that she can't forgive you, returns to the subject to pick at old wounds, it may be better for the both of you to take it as a lesson learned and go your separate ways.
  
  A:
  
  Firstly, please take a good look at what you have actually written.
  You wrote that:
  
  You need to tell her because it is "eating at you"   
  When you tell her, she will likely react with "self-consciousness and mistrust".
  She is already very bothered that you have more "experience" than she does.
  It was "selfish of you to withhold the information" in the first place.
  
  So you want to tell her in order to make yourself feel better even if it makes your girlfriend feel worse?
  It sounds to me that if you do this, you are just being selfish again.
  You didn't do anything so terribly wrong. You may have had selfish reasons but you were also protecting her feelings. You also avoided revealing secrets between you and your ex-es who also have their rights to privacy.
  Your whole reasoning is in fact so flawed, that I need to ask you: Are you sure that all this is not an elaborate self-deception aimed at achieving some other goal. Perhaps you are looking to hurt your girlfriend or feed her doubt? Perhaps you want her to break up with you?
  I really suggest you talk to a therapist or at least a very good friend before you go through with this.
  
  