How do I tell my fiance about a bad boy we both know

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I have a situation that I feel guilty about and could use some advice.

I recently got engaged to a wonderful man who means the world to me. He is just a great guy all around and I want to spend my life with him. We are compatible inevery way even if our backgrounds differ a bit – and by that I mean our sexual histories.

Matt ”is a “good guy” and has only had 2 previous partners, both long term. I’ve hadmore than that. We never exchanged actual numbers, but we did have a couple oftalks because he’s very big on marrying a girl, who as he says, “shares hisvalues.” He said he can accept that I’ve had “some partners” but he does notwant to meet any of them but if we were to run into any of them to tell him. Isaid no problem and that I’ve had “so few” that this would probably never happen.

Well, there is a guy, “Joe” who is part of our social circle. Matt doesn’t like him because he views him, accurately, as a player who doesn’t respect women. He disapproves when we see him at some party or function with a different girl everytime. Matt shakes his head and always tells me how incredibly gullible some women must be to fall for Joe’s *hit.

My problem is that in the past Joe and I were “together.” He was the bad boy thatI thought I wanted. We spent a couple of months together in an anything goes sexual relationship. I wanted more, Joe did not, and we both moved on but remained friendly.

I’ve never told Matt about Joe. Joe has been over to our condo numerous times. I feel guilty about not telling Matt. What makes it worse is that Matt trusts me completely. He’s told me about fantasies he has that he would like for us to try together since it would be “new” for both of us. In fact, even though I have not told him this, none of what Matt wants to try is new to me. Joe and I pretty well did everything and I feel guilty that I did stuff with Joe that I would love to have done only with my “One and Only,” Matt.

I guess I’m scared about how bad Matt’s reaction will be if I tell him – I know for a fact it will be negative. Joe does not know that I have not told Matt so there’s always a chance he could say something stupid.

How do I move forward with this delicate situation that I am feeling increasingly guilty about?
 
You essentially present two options: lie to your fiance or tell him the truth.

I recommend the latter.

If your fiance is truly a “good guy,” he will understand and forgive you. This is not to say he will not feel upset or jealous to some degree, but if all you’ve said about him is true, he will be compassionate. Up to this point, you both have been honest with one another, and I think you owe him total honesty in return.

Also, the truth will always out, especially if you’re trying to conceal a truth regarding a person who is currently in both of your lives. This “Joe” character is, by your own admission, untrustworthy and unreliable and it is entirely likely that he might let something slip at some point at a social gathering or Matt may find out about this from someone other than you. That, more than anything else, has the potential to destroy the trust between you and your fiance.

I will add, easy though it might be for me, a disembodied voice on the internet, to say, that if Matt reacts badly to this and rejects you, he’s not worth your devotion any how.

God bless, and best wishes.
 
Only having two previous sex partners does not make Matt a good guy. One or one hundred and one makes no difference. A fornicator is a fornicator. If you cannot be honest with Matt now then you should not consider marriage. It is bound to come out sooner or later and the consequences could be horrendous .
 
You essentially present two options: lie to your fiance or tell him the truth.

I recommend the latter.

If your fiance is truly a “good guy,” he will understand and forgive you. This is not to say he will not feel upset or jealous to some degree, but if all you’ve said about him is true, he will be compassionate. Up to this point, you both have been honest with one another, and I think you owe him total honesty in return.

Also, the truth will always out, especially if you’re trying to conceal a truth regarding a person who is currently in both of your lives. This “Joe” character is, by your own admission, untrustworthy and unreliable and it is entirely likely that he might let something slip at some point at a social gathering or Matt may find out about this from someone other than you. That, more than anything else, has the potential to destroy the trust between you and your fiance.

I will add, easy though it might be for me, a disembodied voice on the internet, to say, that if Matt reacts badly to this and rejects you, he’s not worth your devotion any how.

God bless, and best wishes.
This is really good advice. 👍
 
Only having two previous sex partners does not make Matt a good guy. One or one hundred and one makes no difference. A fornicator is a fornicator. If you cannot be honest with Matt now then you should not consider marriage. It is bound to come out sooner or later and the consequences could be horrendous .
Good people sin all the time. A sinner is a sinner and we are all sinners.
 
You need to talk to him. You can either wait until he brings it up, or you can bring it up yourself: The topic of the “new” things he wants to do…“Matt, I was ashamed to say this before, but I’m more experienced than you think. Whatever you want to know, I’ll tell you, but I don’t know what to say other than that. It’s something that is going to be very painful for me to talk about, but I know you have a right to know. If what I’ve said so far is all you need to know, I’ll understand. I’m so sorry, but I can’t undo my past. Believe me, though, I wish I could.”

If you’re smart, you’ll do this before Joe (or someone who knew you were “an item”) opens his big mouth and does it for you.
 
Matt ”is a “good guy” and has only had 2 previous partners, both long term.

. He’s told me about fantasies he has that he would like for us to try together since it would be “new” for both of us.
I am feeling increasingly guilty about?
please don’t think for a second that he is a good guy,talking about fantasies of what he wants to do to you, is not a sign of a good guy.he is a user .run ,don’t walk away !
 
I’ve never told Matt about Joe. Joe has been over to our condo numerous times. I feel guilty about not telling Matt.
“Our condo”? Are you cohabitating with Matt before marriage? If so, you have bigger problems than just an ex in common.
 
please don’t think for a second that he is a good guy,talking about fantasies of what he wants to do to you, is not a sign of a good guy.he is a user .run ,don’t walk away !
Where did you see that? All I see is she said he has fantasies about things “that he would like for us to try together.” There’s a HUGE difference.
 
I have a situation that I feel guilty about and could use some advice.

I recently got engaged to a wonderful man who means the world to me. He is just a great guy all around and I want to spend my life with him. We are compatible inevery way even if our backgrounds differ a bit – and by that I mean our sexual histories.

Matt ”is a “good guy” and has only had 2 previous partners, both long term. I’ve hadmore than that. We never exchanged actual numbers, but we did have a couple oftalks because he’s very big on marrying a girl, who as he says, “shares hisvalues.” He said he can accept that I’ve had “some partners” but he does notwant to meet any of them but if we were to run into any of them to tell him. Isaid no problem and that I’ve had “so few” that this would probably never happen.

Well, there is a guy, “Joe” who is part of our social circle. Matt doesn’t like him because he views him, accurately, as a player who doesn’t respect women. He disapproves when we see him at some party or function with a different girl everytime. Matt shakes his head and always tells me how incredibly gullible some women must be to fall for Joe’s *hit.

My problem is that in the past Joe and I were “together.” He was the bad boy thatI thought I wanted. We spent a couple of months together in an anything goes sexual relationship. I wanted more, Joe did not, and we both moved on but remained friendly.

I’ve never told Matt about Joe. Joe has been over to our condo numerous times. I feel guilty about not telling Matt. What makes it worse is that Matt trusts me completely. He’s told me about fantasies he has that he would like for us to try together since it would be “new” for both of us. In fact, even though I have not told him this, none of what Matt wants to try is new to me. Joe and I pretty well did everything and I feel guilty that I did stuff with Joe that I would love to have done only with my “One and Only,” Matt.

I guess I’m scared about how bad Matt’s reaction will be if I tell him – I know for a fact it will be negative. Joe does not know that I have not told Matt so there’s always a chance he could say something stupid.

How do I move forward with this delicate situation that I am feeling increasingly guilty about?
My wife and I both had numerous partners before we met. She works with a couple of them since she has been in the same industry for 20 years. We both had come to a point in our lives that we saw the harm of what we did in the past. Then God put us together. We were on the same page about sex before marriage and waited untill marriage to have sex. I didn’t have a problem with her past relationships, even though some were still around, because I knew she was a different person.

That’s the key. He has to know you are not the same person you were when you were with this other guy. You say he has “values” if he is having sex with you before you are married he doesn’t have God’s values and that’s all that matters.
I say show him you are not the same person and tell him you want to wait until you are married to have sex from now on. If your giving it up freely for him why wouldn’t you give it up for this other guy again? That’s what he will think other wise.
 
You know what? This is none of Matts business. You are NOT telling lies by omitting this information. If having Joe around makes you uncomfortable, gradually distance yourself from him, if Matt is that important to you, you should end the friendship. However marriage is not a license to know each others dirty past. When our sins are forgiven we are born anew. I think it is better to slowly phase Joe out of your life, I am pretty sure guys like Joe understand that kind of thing if they are worthwhile as friends (at least the Joes I have known…) and if he’s not worthwhile as a friend, you shouldn’t have him as one anyway.

Also it is not a lie to discuss the things you will try with Matt, trust me, it will be completely different and new if it is performed in the marriage bed with a man you love and trust and have committed to. Matt doesn’t need to know you’ve already tried the physical side of things. Still, you probably shouldn’t be talking about those things so intimately anyway - its because of BOTH of your past sins that you can do this so comfortably.

Also your fiancé is no better than you, coming to marriage with that attitude is really going to be bad for you, he really does not have any moral high ground, as others here have also said. I think there are more issue here than just a drama with “Joe”. Please ask yourself why are still friends with Joe. If he is the one who got away, having him around as a friend is probably not a great idea anyway. Maybe its time to let go.

edit: I just wanted to add, that it was wrong of Matt to ask you to tell him if you run into any old partners. This is just games and power play. This sort of thing is more about Matt than you. There can be no good intention for wanting to know this information. He may want to compare himself to boost his ego, or indulge in insecurity. He may want to use it against you. This was not an honourable thing to ask of you. Only a priest and a court of law have a right to ask details about past sins. The first asks to absolve you and the second asks to judge you. If Matt appoints himself to do either he is not approaching you as your loving equal.
 
This is a difficult situation, since it sounds like Matt doens’t really want to know about Joe. (And he probably is right in this, since it wouldn’t do much good for you guys.) Unfortunately, there is a chance that Joe might feel the need to talk to Matt about you. I don’t supose that there is a gentle way to extract Joe from your life? It’s pretty inappropriate for you to remain friends, in my opinion. Could you simply let Matt know that you aren’t comfortable with Joe around because he used to be your boyfriend? You wouldn’t have to go into all the details about what you and Joe did, particularly if Matt doesn’t want to hear about it. (And he probably doens’t.)

It sounds from your post like you are cohabitating and that your finace fantasizes about “new things” that he didn’t do with his previous partners. I’m not sure what “new things” entails, but unless it amounts to sharing frequent physical renewal of the sacrament of marriage in a way that is both procreative and unitive, I’d be a little concerned about that mind set. Perhaps it would be a good idea for yourself and your fiance to talk to a priest or maybe your focus couple about some of the “new things” God has in store for those who experience the marital embrace according to His plan. I would hope that he would find such ideas to be intriguing and exciting and maybe that will keep his imagination off of more banal fantasies. (And you won’t have to worry about the fact that you went through the motions with Joe or whoever because spiritually speaking, it’s not even remotely the same thing.)
 
Hi everybody. thank you for your comments and suggestions. I’d like to respond to some of them.

Gliggleasked if Joe is the one that got away. No. Joe was a mistake. He basically used me like he has alot of other women. Matt knows that Joe is a womanizer so if he finds out, he would think that I was just another nummber to Joe. Not a good feeling for him I’m sure.

Matt IS a great guy. He does not play games and he’s not insecure. But I know that if Joe blabs Matt will look at me differently. I just wish I could make it up to him without him flipping out.

Also, I can’t really detail it here but there are reasons why we can’t completely “move away” from Joe. It’s unfortunate but Joe is in our social circle.
 
Hi everybody. thank you for your comments and suggestions. I’d like to respond to some of them.

Gliggleasked if Joe is the one that got away. No. Joe was a mistake. He basically used me like he has alot of other women. Matt knows that Joe is a womanizer so if he finds out, he would think that I was just another nummber to Joe. Not a good feeling for him I’m sure.

Matt IS a great guy. He does not play games and he’s not insecure. But I know that if Joe blabs Matt will look at me differently. I just wish I could make it up to him without him flipping out.

Also, I can’t really detail it here but there are reasons why we can’t completely “move away” from Joe. It’s unfortunate but Joe is in our social circle.
If you just tell Matt that you and Joe dated, then Matt can be prepared to shut Joe down if he ever feels the need to “share”. You don’t have to share any gory details.
 
Hi everybody. thank you for your comments and suggestions. I’d like to respond to some of them.

Gliggleasked if Joe is the one that got away. No. Joe was a mistake. He basically used me like he has alot of other women. Matt knows that Joe is a womanizer so if he finds out, he would think that I was just another nummber to Joe. Not a good feeling for him I’m sure.

Matt IS a great guy. He does not play games and he’s not insecure. But I know that if Joe blabs Matt will look at me differently. I just wish I could make it up to him without him flipping out.

Also, I can’t really detail it here but there are reasons why we can’t completely “move away” from Joe. It’s unfortunate but Joe is in our social circle.
At some point, you’re going to have to say, “You’re right, and I should know. I have been ashamed to admit it, because it was so stupid, but I was one of those idiots that was stupid enough to date Joe. He’s a charmer and a user and I honestly wish I’d never given him the time of day.”
 
To EasterJoy: Yes, for sure that’s what I’d say. But I know how guys think. He’s going to flip that some d-bag “got me” and "knows"me
 
It concerns me that you are more comfortable confiding to anonymous Internet strangers about your sexual past than with your husband-to-be. It is starting to sound like Matt has jealousy issues. You need to work these out well in advance of a wedding date. Is one or both of you Catholic? Are you being married in the Church? How is your pre-Cana wedding prep going then?
 
To EasterJoy: Yes, for sure that’s what I’d say. But I know how guys think. He’s going to flip that some d-bag “got me” and "knows"me
Doesn’t he know that you have had multiple sex partners already? So, no offense, I wasn’t a virgin when I married, but technically multiple guys “got you.” 🤷
 
To EasterJoy: Yes, for sure that’s what I’d say. But I know how guys think. He’s going to flip that some d-bag “got me” and "knows"me
“Well, think about how I feel. It’s not like it was a one-night stand. We dated for several months. It was really stupid, but I imagined we would stay together, just as I’m sure many have, both before me and since. The guy said all the right things, OK? I think by now you and I both know that this is why we’re supposed to wait until we get married, which neither you nor I did. I know this is hard on you, but I’d really rather drop the subject.”

Provided that you do not lie and say you are keeping nothing private of the sort he might ask about, you can keep certain things in your past private. He has to know that certain things are there, but refusing to give every intimate detail is not malicious deceit!

Not every guy thinks the way you’re describing, BTW. Some of them think, “Well, I’ve made my mistakes, too, and done things I deserve to be ashamed of…not stuff I’d brag about to Mom. As long as I can trust her and she can trust me not to repeat any of those past sins, as long as we can each forgive the other for having a past that is not as pure as we ought to have to offer each other, then we’ll just have to get past it. It is not what God intended, but it is what we have to cope with, and we’ll just have to cope with it together.”

PS Honestly, why you guys spend any time with this guy when you think as “highly” of him as you do is beyond me…but then, charmers seem to be rewarded with a social life like that all of the time. Go figure! 🤷
 
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