Jezzie Cries Herself To Sleep Since Her Boyfriend Lied To Her

Jezzie asks:
I've been with my boyfriend, James, for nearly 18 months, everything has been great apart from about a year ago it came out that he had a sexual encounter with his boss not long before we started going out.
It really hurt me but I decided to forgive him because I love him so much. Because I was so hurt he decided to quit his job, which I really appreciated. I read the emails he sent to his boss explaining why he was quitting and in the emails I saw that he had lied about when the encounter happened.
It actually happened a day before our official "anniversary". The fact it was so close to when we made things official really upset me because at that point I thought it was obvious we were going to become boyfriend and girlfriend and it felt like I had been cheated on and lied to for 6 months.
The fact he LIED to me made me lose some trust in him and worried that he was lying about more details. I know he was just lying because he didn't want to upset me more, but it ended up me being more upset than I would have been if he'd just been 100% honest.
Also, it hurt more because his boss was part of his friendship group and I had become quite friendly with her before I found out what happened between them, and I felt like she probably thought I was stupid for going out with him and being completely innocent what happened between them.
After I found out we stopped hanging out with her as much as possible, but James still has to see her occasionally as one of his colleagues from his old job is his best friend. This doesn't bother me because I know he would never do anything with her now, but it's just the fact he tries to keep it quiet when he's hanging out with her and it makes me think he's got something to hide.
I haven't seen her since I found out and I think if I did I would get very upset or angry. Even though he initially lied about when it happened I forgave him still, again out of love and because he seemed genuinely very sorry and upset at the possibility of me leaving him.
But even though I have forgiven him, I cannot forget what happened and a year on I still get upset at the thought of it and cry myself to sleep some nights.
I can't keep bringing it up with James as I feel like I'm never-ending punishing him for a mistake he made and when I do bring it up he gets super upset/angry.
I feel like the only thing that can heal this pain is time but I don't want to waste years trying to get over this if I never will because I'm only 19 and if I'm not with "the one" then I think I might as well not be in a serious relationship, because isn't your youth the time to be single and have fun?
You’ve really been hurt badly haven’t you, Jezzie? And it’s not surprising. What you identify is the fact that you could have coped better with the truth, no matter how much you wouldn’t have liked that either - but to have a confession that then turns out to be a lie, is somehow much worse.
Your insecurities in this sorry story are all well founded - of course you wouldn’t like it when he hangs out with this woman, even if it’s his friend he’s actually going to see. The fact that he gets angry or upset when you bring it up isn’t reasonable at all - but suggests he feels guilty and knows that nothing he can ever do will make up for it.
If he brushed it off as if nothing had happened, maybe you’d feel even worse. Chances are, unless you can take these feelings and mentally push them to the back, they’ll haunt you for a long time to come, as you fear.
Try telling yourself that it happened in the past and that whatever happens in the future, you won’t keep bringing them up. Promise yourself that you won’t pull it out of the bag in future arguments. If you’re sticking with him, then you have to accept it happened and put it in the past.
If you don’t think you can, and you think that it hurt you too much, then walk away and tell him that although you love him, what he did spoilt everything you had and left you feeling like you could never trust him again; and make it clear that it wasn’t so much the fling he had with his boss but the way he lied about it subsequently.
Make sure you let him know you didn’t want to walk away but that you simply have no choice because you don’t want it to change you as a person.
Say you came in to the relationship an optimistic, trusting girlfriend and you don’t want to end up bitter and twisted. Truly, I would recommend walking away from the situation - as you say, you are young, and it’s too young to be having years ahead of these feelings. You’re right - you can’t keep making him pay forever.

If you love him, just pull yourself together and get over it. Okay, so he lied - by the sounds of it, he was lying because he thought he’d lose you if you knew the truth (a pretty safe bet, I’d imagine, for most people).
So although it doesn’t excuse him, it does suggest that he wants to be with you. If he didn’t, he’d have walked out on you after his misdemeanour with his boss, if not with her, then he’d have developed a taste for the excitement of it all.
But it sounds as though he’s realised he wasn’t treating you properly and attempted an admission of guilt. It went horribly wrong but the reason he’s getting angry when you mention is that he’s actually angry at himself but he can’t show that.
Just accept that you’re both young, you’re both going to make mistakes, and that you have something worth saving.
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