So I've been dating my boyfriend for a couple of months now. We dated in high school and broke up and two years later, we're back together and madly in love. We're committed and know we want to get married in the future and there's nothing I could complain about with him. But I constantly find myself thinking about his ex-girlfriend. When I dated him back in high school, he was very naïve and a virgin. I was his first official girlfriend. After he broke up he dated this one girl he had a crush on since middle school. But when we started talking again this summer and I found out he was in a sexual relationship with her, it really bothered me. Like extremely. I can't get over it. I said this to him initially but haven't brought it up since. I think I'm jealous at the fact that I wasn't his first, and that I had that opportunity but threw it away due to breaking up with him. I wanted to have that privilege. It especially bothers me because not only does he describe that relationship with his ex to be an utter waste of time, but she cheated on him as well. He's such a great guy and doesn't deserve that treatment, so it makes me angry. The type of girl that he and others describe her to be is someone that's undeserving of a guy like him. It just bothers me that I can't do anything about it and it constantly looms over me. I even find myself going on her FB page occasionally. I'm at a loss as to what to do and I wonder why it's such a big deal to me.

You are stalking her page because had sex with her? This makes no sense. How old are you?
You get over it before it ruins your relationship. Do you think you may be jealous of what she had with him? You have him now. Why did you break up with him?

You were not a virgin when you got back with him but are upset that he wasn't either? And he didn't even have a happy relationship with her? Good God, if this is really what you are obsessing over, you have a truly serious kind of narcissism. Get some help if you can't talk yourself into squashing it.

We ALL have funny little jealousies. A sweet example of this is wishing we had known someone we love their whole lives, even when they were babies, or at least years earlier. But your situation is poisonous, and it's going to ruin a good thing. Do you WANT to ruin a good thing? Are you willing to work on this, telling yourself constantly how selfish and irrational it is, and how you are going to lose him, because you won't be able to enjoy him?

You are looking for trouble where none exists, and it does sound very selfish of you to hold his past with such importance. If you started a relationship with him 10 years in the future, and he had significant relationships, or frequent sexual activity with many others, would your head explode?

You are jealous of a ghost. He told you how miserable the relationship was with her, and was honest about it. It's over, and likely not even in his thoughts, and hasn't been, for a long time. One of the mistakes he made, and regretted, and believed it over enough to tell you all about it.

He doesn't owe you an explanation of anything he did while you were not together. What he brings into the relationship with you, is all you have to worry about. Not to mention that you already have a volunteered 'confession', which you've turned into a part of your relationship with him, by stalking her, and by continuously feeding the flame of insecurity, by keeping that old relationship, alive.

It's dead. Joy is right- keep this up and you'll ruin a good thing. That cloud over your head is something only you can shake off.

You know what you should do? Think about it 24/7, let it consume you, let it control you, let it ruin your relationship.

Really, is that what you want?

Let it go. Think of it as basic training where he worked out the kinks. He was free to do whatever he wanted to do with whomever he wanted to do it with. It is not realistic to expect him to wait for you in the chance that you two might get back together. The man had needs and it is a normal thing to meet those needs. So let it go.

Look at it from another angle (not that any more are needed):
He had a crush on her since middle school. Be GLAD that he got it out of his system. What if he carried a torch for her throughout his life?