Cheating? Cheating? Cheating? Please help!?

I don't think it will necessarily happen due to a fight, or boredom, or you being out of town. But I do think he will almost certainly cheat on you if he ever gets the idea that your relationship is broken and he "knows" you're going to break up soon anyway.

I don't believe in "Once a cheater, always a cheater."

It's just a silly saying ~ a crutch for the undiscerning. It doesn't account for those who actually learn from their mistakes, and those who really do change.

In your case, you need to figure out what your boundaries are. If you have zero tolerance for cheating, then decide what you will do should your boyfriend ever cheat on you. If you decide the relationship would be over, then be prepared to actually do it if that becomes necessary. Then communicate that clearly to your boyfriend.

After that, enjoy the relationship. Don't spend your time checking up on him or questioning him about his previous relationships, or talking about how fearful you are about his level of faithfulness. Take things at face value and don't try to interpret his words and actions through your fears.

But if the day comes when something about him doesn't add up, then start paying closer attention.

I do think it's possible for people to change. Possible but not likely. It sounds like he has trouble staying faithful when he feels that the relationship is on the rocks, or not something he sees as serious. That doesn't necessarily mean he'll cheat in other situations, but it does mean that when the going gets rough for you guys (and eventually it does in every relationship) he may see that as an excuse to repeat the behavior. You also have to consider the fact that even if he doesn't return to that pattern, you may never feel comfortable trusting him because of his past. If the trust isn't there, it will be hard to stick together over the long haul.

I don’t agree with “once a cheater always a cheater” I used to cheat left and right on guys just because I could, I assumed they were cheating, figured the relationship was going to end anyway, etc. I have the most amazing man in my life whom I love and would never ever hurt no matter what because I care about HIS feelings too!!! Don’t believe that just because he has done it to SOMEONE ELSE means that he WILL do it to you. You know how he feels, go with your heart and your gut.

Seriously as much as i hate to say this i do believe once a cheater, 99% of the time will stay a cheater. There is that 1% chance that he wont ever cheat on you (of course ive havent actually seen any studies to come up with my percentages) but I dont think you should dump him if he hasnt given you reason. Just keep your radar on overdrive so youll know if he does then leave... I agree with J, you shouldnt have to worry that if you guys start having problems that he is going to decide thats reason enough to go cheat on you. I just dont know about this guy, really sounds like a risky guy to be commited to.

You took a long time to say that you don't trust him. It's like you're just waiting for him to cheat then you will know for sure that he's really a cheater and you were right not to trust him. You sound like someone who's been cheated on. Why is he even talking to you about a past relationship? That was then, this is now. Who initiates these conversations, you or him?

Honey if you already have proof he is cheating ("So I think my bf is cheating doing the online thing I do have proof, but he hides his "cookies" temp files that can trace what you are doing online.. ") why would you want to continue torturing yourself looking for more evidence? Just kick him to the curb noone deserves to be cheated on. I know its easier said than done because I'm sure you love him, but love yourself more. No guy is ever worth your tears.

hes dated 14 years so that tells me hes had years of life experience and now could b more maturer. its good that u question him thou your radar is up and going girl. listen when guys r young anything is possible u can tell sometimes by watching and listening to him if he has grown up other guys at your bf age they r pros and they can blindside u easily depends on if your one of those women who just dont want to believe the truth if it hits u in the face. but u sound pretty wise and i dont think hes going to get past much with u. is he a bull shitter or a lier? because if he is u might have problems, does he like to b in the center of attention? or does he content with only your attention. i dont blame u for being worried thou and u know what tell him that u dont like to b that way and u r trying that u just dont know if hes outgrown his cheating ways, heck u dont know if hes going to get bored with u too. tell him u want total honesty nothing less.

I agree with "once a cheater, always a cheater". As nice as he sounds, I'd be wary. You are right to be scared - at any point, he can decide that your relationship is "broken" and use it as an excuse to cheat.

Imagine if someone was examining every step YOU take and trying to reason it. How would you feel. They assumed because you took 2 steps to the left then you will take one to the right ( pattern). This is exactly what you are doing to him. You are thinking way too much and trying to examine his step and make sure he never cheats on you. Well guess what. You can't and you shouldn't. You either trust him or just leave. Please don't put a lease around someone. My wife tried that on me and we almost got a divorce. good luck