Ok so just got dumped after a short relationship, which was a bit of a kick in the face for me as actually we were going along very strongly. Managed to get said girl on the phone to find out why this had happened. We went out a few days ago and had a lovely day together where we were opening up to each other and she asked me about my past and whether I had ever cheated on someone. Being the honest twat that I am I said yes a few years ago but (and this is the truth) I felt fucking awful about it afterwards and could never bring myself to do it again.

So when I get said girl on the phone to find out why she decided sack things off, she said it was because of the fact I had cheated. She had had it done to her in the past and it was a full on deal breaker for her - she said it bought up lots of bad memories and she would not be able to trust me. I felt like punching myself in the face.

The big question that has come out of this failure for me (apart from 'how could I have been such a knob') is how much of your past should you divulge and how much of your past should you hide away and never, ever let anyone know about?

LOL well I would have said don't talk about cheating....

Talk about how you were a weaker person and have grown as a man. Don't talk about failures unless you have since seen success. Don't talk about fuck ups unless you have since redeemed yourself.

As much as I'd love to tell you to do the right thing and tell the truth, the fact is that it won't do you any favors. You have acknowledged cheating is wrong and you say you won't do it again, and I think as far as morals go, that's good enough as long as you follow through with it. No need to tell people. It's your personal business, anyway.

In my opinion, avoid the question at all costs.

If she asks you the direct question, say just once and it was only to get even with a girl who had wronged you first.

We all lie on way or another. This one is the kind you want to lie on.

How would you feel about a girl you just started seeing telling you that she has cheated in the past, but she totally stopped?
That's how she felt.

Actually I probably wouldn't give a crap because its her past and people shouldn't be judged on what they have done in their past only what they have done now. But my opinion isn't hers so I understand why she did what she did. But it still doesn't change the question, if she asks should you tell about your past. I mean if you hide something away, it usually comes out at some point in the future right?

When you would want a girl to be your girlfriend, I'm never in favor of lying, so if it's true, tell her you did cheat, felt awful afterwards and elaborate about how you have grown as a person and what went wrong. It will put off some girls. Whether you want to lie (and risk her doubting your answer/finding out later) is up to you oc.

If it's just casual and you don't want anything serious, I think it's rather your personal business.

If you don't learn from history you are doomed to repeat it. The saying "once a cheater always a cheater" exists for a reason.
As for yourself, lie when you have to. Just don't get caught with your pants on fire (or down). Won't make you a better person, but admitting to having cheated in the past wont make you any less likely to do it again (if not more because of the impending insecurities, jealousies). Hopefully your personal life is private enough that scandalous revelations of you won't be popping up years down the line. If you want to be a good person treat her well now. That's what matters more.