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You Asked: Should I Have Been Honest With Him After All?

Dear Sugar,
My boyfriend and I have been dating for five months. I recently told him about how I cheated on my past two boyfriends and he flipped. He told me that he no longer trusts me and wished that I hadn't told him because now he's always going to wonder if I'm cheating on him. I just wanted to be honest with him before he heard it from my friends, but was that the right thing to do? I'm so confused! I've never given him any reason not to trust me but I feel like I just dug my own grave. Is this just a harmless misunderstanding that will make us stronger or is this a deal breaker?
— Regretful Regina

To see Dear Sugar's answer

.

Dear Regretful Regina,

I'm a big proponent of honesty, so I don't think you should regret your decision in the slightest bit. Since you've given him no reason to distrust you, something tells me that he's been cheated on before, which is making him guarded towards you. You're still getting to know one another so explain to him that the only reason you told him was to set an honest precedent for your relationship. Sure, I can see why your boyfriend might be a little wary about your cheating past, but the fact that you were upfront and honest about it should give him some reassurance that you learned your lesson from your mistakes.

Only time will tell if this will make your relationship stronger or tear you apart, but Regina, I hope this doesn't deter you from being honest about your past, your feelings, or your desires. Although this was an isolated incident, he could be using this as an excuse to break up so proceed with caution and I hope it all works out for you. Good luck.

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Minou Minou 7 years
Sorry, but I just felt strange about the above comment. "I am a very honest person, and I am assuming you are also. If they cant handle an honest woman, then they do not deserve us anyway." Neither of you can be honest (forget 'very honest') once you cheated/cheat. Having that kind of attitude means you didn't learn from your lessons. Actually there's no best advice here. It really depends on how tolerant a person can be, of course he is no position to forgive you, since he wasn't cheated on by you. So either never tell a person the details of your cheating past or tell with as many details as possible why you should ever cheated. Although being an open book to our loved one is not a bad idea, there is something that's better not known.
Minou Minou 7 years
Sorry, but I just felt strange about the above comment. "I am a very honest person, and I am assuming you are also. If they cant handle an honest woman, then they do not deserve us anyway." Neither of you can be honest (forget 'very honest') once you cheated/cheat. Having that kind of attitude means you didn't learn from your lessons. Actually there's no best advice here. It really depends on how tolerant a person can be, of course he is no position to forgive you, since he wasn't cheated on by you. So either never tell a person the details of your cheating past or tell with as many details as possible why you should ever cheated.Although being an open book to our loved one is not a bad idea, there is something that's better not known.
watereatsrock watereatsrock 7 years
I was recently in a very similar situation with my bf. I am a very honest person, and I am assuming you are also. If they cant handle an honest woman, then they do not deserve us anyway. On another note I am going to withhold any information about my past relationships from now on. Since he obviously cannot handle it.
Silverlining10 Silverlining10 7 years
I always thinks honesty is the best policy, but telling him you were unfaithful in your past relationships will definitely put some pressure on you. Naturally, he'll be worried, but I think if you continue to be faithful, he'll realize you've changed. You already told him your past, so you can't erase that, but if you've changed for the better, then he'll be able to see it. If he's too insecure, and thinks he just can't trust you at all, that's his problem.
fran441 fran441 7 years
jacrabbit84, cheating is not a reflection of whether you're with the right person or not - it's a reflection of the kind of person the cheater is.
AshleyMay84 AshleyMay84 7 years
He needs to grow up. You cheated on two guys in THE PAST. This does not pertain to THE PRESENT. He should be grateful that you were willing to give enough of yourself to be honest with him. If he can't accept the mistakes that you've made, then he does not deserve to have you.
AshleyMay84 AshleyMay84 7 years
He needs to grow up.You cheated on two guys in THE PAST.This does not pertain to THE PRESENT.He should be grateful that you were willing to give enough of yourself to be honest with him.If he can't accept the mistakes that you've made, then he does not deserve to have you.
hotstuff hotstuff 7 years
Your boyfriend has no right to be mad at you because you cheated in the past. Its not like you've cheated on HIM! He has a hell of a nerve if he asked you this question and then got all upset because you were actually HONEST with him. I think he's showing you a side of him that YOU should take a closer look at. I mean, so does he think he now has a right to throw this in your face in the future and to be mad at you because were telling the truth? I'd tell his ass to go kick rocks. It just goes to show you have to be honest in your relationship but there are just some things you can't tell a man. If he asked then yea tell the truth but if you just offered up this information your crazy. I think a good rule of thumb is to keep past relationships in the past. And seriously fear that your friends would bring it up? What the hell type of friends would that be....."Hey Earl did we ever tell you about that time your girl cheated on her past two boyfriends"? Seriously.
ninjastarlett ninjastarlett 7 years
I think it would have come up eventually anyway... so the choice comes down to whether you want the relationship to be smooth-sailing (not tell him about the previous cheating) or to endure some hardship and theoretically be stronger for it (tell the truth).
thelorax thelorax 7 years
It's definitely better that he heard this from you rather than a backhanded comment from one of your friends! IMHO you were on the right track by being forthcoming and honest - maybe he just needs some time to "cool off" and process this. In the meantime, do everything you can to make him feel exclusively loved - assure him that he is everything you want and all that you need (unless that isn't the case - which is probably the story with the last two guys - meaning you need to start picking better guys!). Hope everything turns out OK...and no more cheating! If you don't really like the guy then BREAK UP WITH HIM, and THEN find someone else. Good luck!
fran441 fran441 7 years
Unfortunately, what you were being honest about was being deceitful and untrustworthy. Do you know you're not going to cheat on him? How do you know? What's changed since the last boyfriend? The willingness to cheat, especially repeatedly, is a serious character flaw that anyone should be wary of. I agree with jennifer76, if this was someone who was writing in because her GUY had just confessed to being a serial cheater, most posters would be telling her to seriously question his character and the relationship! They would not be telling her she had a problem with insecurity and that she was being a baby! You're going to have to earn his trust. Of course, if you cheat on him, he probably won't find out about it until the relationship is over - too late to dump you.
fran441 fran441 7 years
Unfortunately, what you were being honest about was being deceitful and untrustworthy. Do you know you're not going to cheat on him? How do you know? What's changed since the last boyfriend? The willingness to cheat, especially repeatedly, is a serious character flaw that anyone should be wary of.I agree with jennifer76, if this was someone who was writing in because her GUY had just confessed to being a serial cheater, most posters would be telling her to seriously question his character and the relationship! They would not be telling her she had a problem with insecurity and that she was being a baby!You're going to have to earn his trust. Of course, if you cheat on him, he probably won't find out about it until the relationship is over - too late to dump you.
RockAndRepublic RockAndRepublic 7 years
Maybe what you shouldve done was figure out why is it that you behave the way you do.
GlowingMoon GlowingMoon 7 years
You screwed up. You left your past behind. It's NOT who you are now. So why did you bring up your past?? There's a difference between honesty and full disclosure. They're not the same thing. You practiced full disclosure. VOLUNTARY full disclosure, I may add, and sometimes that's unwise.
GlowingMoon GlowingMoon 7 years
You screwed up. You left your past behind. It's NOT who you are now. So why did you bring up your past??There's a difference between honesty and full disclosure. They're not the same thing. You practiced full disclosure. VOLUNTARY full disclosure, I may add, and sometimes that's unwise.
erratic-assassin erratic-assassin 7 years
hmm...it's almost the same as "would you date a guy if you knew he cheated on his past 2 gf's?" I still think it's only fair you told him. better it come out now than on a drunken night...something may slip and THEN you're REALLY in trouble.
erratic-assassin erratic-assassin 7 years
hmm...it's almost the same as "would you date a guy if you knew he cheated on his past 2 gf's?"I still think it's only fair you told him. better it come out now than on a drunken night...something may slip and THEN you're REALLY in trouble.
7kimba7 7kimba7 7 years
My ex had told me that I was the first girlfriend that he had never cheated on... but then we ended up breaking up because I found out he cheated on me with multiple girls throughout our relationship. Also, if my boyfriend told me he cheated on his last 2 girlfriends, I would also be upset and potentially leave the relationship. That being sad, being judged based on your past mistakes sucks, especially if you have learned from them. I understand that you want to be honest and I don't agree that once a cheater always a cheater, but maybe you should have kept this one to yourself.. though I guess that cat's out of the bag. I guess all you can do is talk about WHY you cheated before and how this situation is different. Good luck!
7kimba7 7kimba7 7 years
My ex had told me that I was the first girlfriend that he had never cheated on... but then we ended up breaking up because I found out he cheated on me with multiple girls throughout our relationship. Also, if my boyfriend told me he cheated on his last 2 girlfriends, I would also be upset and potentially leave the relationship.That being sad, being judged based on your past mistakes sucks, especially if you have learned from them. I understand that you want to be honest and I don't agree that once a cheater always a cheater, but maybe you should have kept this one to yourself.. though I guess that cat's out of the bag.I guess all you can do is talk about WHY you cheated before and how this situation is different. Good luck!
karlotta karlotta 7 years
My boyfriend used to have "more than friendly" conversations with other women online when he was with his ex - and I know that because I was one of them. Despite the fact that he has assured me that he would never do that to me, that he's matured, that our relationship is different, that he realizes how morally reprehensible it was, and that he's learned his lesson, there is a part of me that will always wonder whether he's going to do it to me. I trust him... 99.9%. And I would be stupid not to leave that .1% in the air. If he had actually confessed to cheating on both his exes? I would have run for the door. Doing it once can be a mistake; doing it twice indicates a trend. A certain character. I wouldn't be able to trust you either.
LittleMascara LittleMascara 7 years
To everyone who is saying that she shouldn't have said anything... haven't you ever been embarrassed by an off-the-cuff remark from a friend, then had to deal with the situation later at home? I think that's what Regina may have been getting at, as her reasoning for letting him in on the secret. I know I've been completely embarrassed in situations like that, and had to grill my man about something as soon as we got home... and so has he. I think it was great she was honest, but I think she made her karmic relationship bed by cheating on other people, and she needs to lie in it. Yes, it would make her new man weary, but she needs to explain the situations in which the cheating went down and why she felt compelled to cheat. This way, they can make sure they aren't putting themselves in those situations. Be it unsatisfaction with her current man, or just a drunken mistake. Single out the isses that are pushing you to cheat, and deal with them. Above all else, LEARN FROM THEM!
LittleMascara LittleMascara 7 years
To everyone who is saying that she shouldn't have said anything... haven't you ever been embarrassed by an off-the-cuff remark from a friend, then had to deal with the situation later at home? I think that's what Regina may have been getting at, as her reasoning for letting him in on the secret. I know I've been completely embarrassed in situations like that, and had to grill my man about something as soon as we got home... and so has he. I think it was great she was honest, but I think she made her karmic relationship bed by cheating on other people, and she needs to lie in it. Yes, it would make her new man weary, but she needs to explain the situations in which the cheating went down and why she felt compelled to cheat. This way, they can make sure they aren't putting themselves in those situations. Be it unsatisfaction with her current man, or just a drunken mistake. Single out the isses that are pushing you to cheat, and deal with them. Above all else, LEARN FROM THEM!
lily8206 lily8206 7 years
I think that if you're going to offer up that kind of information it needs to be followed with in depth explanations. If he just thinks you're a serial cheater then of course he's going to be worried - ALL the time! But if you can explain why you felt the need to stray and all the issues surrounding those slip ups, then he should get a clear understanding of why he can trust you in your relationship with him.
lily8206 lily8206 7 years
I think that if you're going to offer up that kind of information it needs to be followed with in depth explanations.If he just thinks you're a serial cheater then of course he's going to be worried - ALL the time!But if you can explain why you felt the need to stray and all the issues surrounding those slip ups, then he should get a clear understanding of why he can trust you in your relationship with him.
Princess-Peach Princess-Peach 7 years
In my mind, maybe telling him that is honest, but above all it's stupid
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