Thanks in advance for your advice. 4 months ago I met an incredible man and we have been dating since. He is 23 and I'm 22. We have a great relationship and I can feel that he truly loves me. Both of us know we share something special and I don't think either of us has felt this way before about anyone. 2 months ago I asked him if he was a virgin (it actually didn't and doesn't matter to me at all I was just curious, I actually regret asking now) and he said yes to which I said I am too. Now the truth is that I have actually tried to have sex with my previous boyfriend but both times I was so tense and "unready" that it was extremely painful and he couldn't penetrate me 100% or at least I think he couldn't fully penetrate me because I have no other experience to compare it to but when he tried it would hurt too much and I would get this strong sense of urination so we could not continue and I told him to stop trying. Months later I started pleasing myself in hopes of "loosening myself" and working on relaxing so that when I am finally ready it can 'work' and during one of these times I bled for 2 days and I think it was my hymen tearing. I am feeling extremely guilty because I feel like I should have explained all of this to him when I said I am a virgin, maybe he wouldn't consider me a virgin after this- whether it actually matters to him I'm not sure of but I feel like I omitted information regarding this and it's causing me a lot of anxiety and sadness. My question is, how do I bring this up and go into further detail about what actually happened? I'm also scared that he will think I'm a liar and/or feel upset by these details because I will be describing trying to have sex with another man but I don't know what to do to ease my guilt and anxiety

You aren't a virgin. Once penis enters vagina, even if it's just a little bit, you are no longer a virgin.

Having said that, it's really none of his business what you did before you met him, and you don't owe him an explanation. Just forget about it and carry on.

How intimate are you two with each other? How emotionally close are you? How much do you really know about each other? Four months tells us nothing.
Only you know if you should tell him everything, and if so, when.
I'd tell him if I were you for only one reason: it's making you feel horrible.
You started this by asking him. Who knows if his 'truth' is any more truthful than yours? You don't.
Let relationships grow without a list of quizzes.

You need to slow down a bit here.

There are different measures, in different cultures, to determine whether a woman is a virgin. Believe it or not, in some cultures a woman who is not a virgin is not as worthy as one who is.

I am assuming you are somewhere in Canada or the USA. Assuming that, I would say the worst thing you did was TRY to have sex, and sex wasn't possible because you were not ready, and it was painful.

Does that set your mind at ease at all?

If that is all you have done, stop beating yourself up over it. Had the 'lie' included multiple partners, a couple of kids, and a few STD's, that would be a red light for anybody.

But all you did was say you were a virgin, and I think you can safely say (without a medical or moral judgment) that you are a virgin. The beginning of sex happened yes, but if that were to be judged even as a consummation of a marriage, I'm not sure it would count because it wasn't completed.

Anyway, just my opinion, and but asking someone if they are a virgin should be off limits, and none of your business in the first place. That can open up a whole can of worms. And anybody asking you the same question, should be flatly told it is none of their business.

And, the relationship is only 4 months old! Learn as much as you can about your boyfriend, know him as a friend, whether you can trust him or not, is he honest, reliable, etc. etc.- the important things to know and be sure of, before you have sex with him. (and finish what you started!)

I don't know if you are a virgin or not, doesn't matter, but since you don't really know yourself, but think you are, then its no lie, and no reason to have guilt or remorse. Enjoy your dating experience without the baggage while you can. Why spoil it with personal baggage you don't understand. You sure don't know if he was telling the complete truth either, and what does it matter?

LOL, maybe he tried to have sex before, but couldn't either, and is as ashamed, and clueless as you are. Regardless NEVER beat yourself up, as maybe you can come clean when you have more knowledge and understanding of yourself and your boyfriend and have progressed a lot further than 4 months of dating.

Things happen the way they do for a reason, and until you know then don't sweat it. You are entitled to leave out details of your own personal business.