Boyfriend who has a history of doing unsavory things

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Hi Guys,

I originally posted this in the wrong section of your website.  Here it is again, in the correct section.  I really need your help on this one, Guys!  Thanx!…

From THE GUYS: We’re assuming names have been changed.

My 44 y/o boyfriend “Joe” and I have been together for 6 months (and known each other for 1 1/2 years. My boyfriend has been “friends” with “Diane” (approx 48 years old) for 15 years (SHE is the step sister of his ex-wife – – Needless to say, the exW and my bf hate eachother, and “Diane” and the step sis hate eachother as well. Yet… Joe and Diane CONTINUE to remain “friends”.

Problems I’m having are these:

1) My boyfriend’s friend is married and has had a VERY rocky marriage.  She continually COMPLAINS ABOUT her current husband WITH my boyfriend. What if this girl is “sexually promiscuous” toward/with my boyfriend????

Diane and Joe say “no, we’re just friends”… I HAVE DIFFICULTY BELIEVING IT, AND CAN’T SEEM TO GET OVER THESE THOUGHTS. Yes, I lack TRUST in him.  Why?  Because of his track record with women… 2 divorces, cheated on first wife 20 yrs ago, used this other woman over the past 3 years for oral sex, and pretty much admitted he used her even though he wasn’t attracted to her.

2) He is VERY protective of this “Diane” friend of his. I can’t say ONE thing about her, or he will jump all over me verbally until I understand that it’s “not my place” to get involved in THEIR relationship.

3) She AND he keep ME out of THEIR relationship. I don’t understand WHY I am not allowed in… In fact, I DON’T even WANT to be part of it, because I DON’T THINK “THEIR RELATIONSHIP” should exist. I THINK THEIR “RELATIONSHIP” is a totaly disrespectful of my relationship with my BF. Am I wrong????

4) Those two call each other daily. They visit each other’s houses atleast 1x/week and supposedly “talk” and “discuss” whatever it is they “discuss” (apparently she vents about her drug addictions, problems with her husband, etc…). Anyway, NEITHER Joe NOR Diane see these daily phone calls/weekly visits as disrespectful of the relationship between my bf and I.

5) She can’t stand me… absolutely dislikes me immensely. She’s told him this. He doesn’t defend “us”. I feel totally insulted, hurt, and disrespected… it’s disgusting to even think about.

Anyway, please let me know what you think of all of this.
What do I do to resolve all of this?

I’ve suggested “all three” of us talking about this, getting it all out in the open. My boyfriend says, “Absolutely NOT!”.



P.S. ….Note to self: As I write this, I wonder, don’t I think enough of myself to NOT be with this man?  What am I doing?  Do I NOT respect myself enough, that I ACCEPT this stuff?

P.P.S. He says he “loves” me about 5-8 times a day.  I say it too.  He calls me every day, we visit eachother every day… we eat dinner together and hang out and talk, watch t.v., laugh, talk about work, say I love you, hug alot, hold hands, and even dance together. But I’m utterly LOST and confused.  I’m also AFRAID he’ll have sex with this “Diane” friend (if he hasn’t already over their “15 yr” so-called “friendship”

Oh, and WHY do I love this guy?  I love ALL the “OTHER” parts of him… except the “unsavory” stuff I mentioned above.  I try not to think about it – – it’s not easy.  I love his hugs and kisses, his softness toward me, the laughs we have, coffee together every morning, the sex, our dancing together, our long talks, and beautiful dinners at home together.  …I love just about EVERYTHING about Joe, except the crummy stuff (if that makes ANY sense).  I suppose one can’t separate the good from the bad, cuz it is all one package.  That’s why I’m so conflicted.

Where do I go from here, Guys.  What do I do?  What OF this DIANE chick?  Why does he choose such a “broken”, “messed up” (to use his words) friend as DIANE to be his BEST Friend (other than me, his supposed girlfriend)?

Too many questions, sorry, but this all hurts so much.  I feel SO conflicted.  I feel like I have no respect for myself, and well… I SHOULD.

Dear Ariana,

Thanks for writing to us.

We see multiple issues going on here. First of all you’ve only been dating “Joe” for six months. And while that is plenty of time to become very close, it pales in comparison to all the history he has with his friend “Diane.” They’ve known each other for 15 years, and have been through a lot of trying times together, which has brought them closer together, however unhealthy it may seem to you.

We commend “Joe” for sticking with his friend, even though it’s clear that she has many issues she needs to work through. (And those issues are way beyond the scope of what we talk about here.) It sounds like they need each other at this point, and maybe through their shared history, they actually help support one another. Remember, this friendship, or relationship, has been going on long before you were in the picture, so it would take a lot to supplant it. Your best approach is to try to understand it and get him to tell you why he values the relationship so much without accusing him, although it may be too late for this since it’s been such a source of discourse between the two of you.

Further more, there’s nothing wrong with a friend of the opposite sex as long as it doesn’t impinge on the primary relationship. However, in your case we agree with you; his relationship with her is starting to impact your relationship because of the close emotional ties he has with her. These ties don’t allow him to be truly open to someone new, but maybe he wants it that way. That’s a larger issue that also needs to be resolved. Why is this relationship so important to him, to the point where he refuses to include you and compromise any aspect of it?

We can’t speak to the physical aspect of their relationship. He says there’s nothing going on and you still wonder. So what’s that all about? Yes, his history is a bit “storied” but people can change. Sure some guys are serial cheaters, but sometimes it’s the situation that brings out that side of people. We don’t condone cheating on any level, but we understand that people are human, and sometimes when people feel trapped, or overwhelmed the behave in unsavory ways. It is true that once you cheat it’s easier to cheat again, but we also know guys who’ve cheated once and wouldn’t do it again. (So they say.) If you’re going to be in a relationship with this guy you have to accept his past and keep it in the past. You have to accept him for who he is now, because all of his past has defined him and made him the man you love—yes, even his moments of weakness with the “other” girl. If he is actually cheating on you currently that’s a whole other story. If that ends up being the case, then by all means you should move on immediately.

Ariana, you need to have trust in your relationship to be able to go the distance. You tell us all the reasons you love this man, but at the same time you don’t trust him at all. That’s quite a disparity, and no way to conduct, or advance a relationship. All it’s doing is making you confused, upset, anxious, and stressed out. And if it continues it will slowly whittle away your self-esteem, and cause resentment and anger. And it goes from there.

So, you need to get him talking. (Maybe couples counseling) If you can’t get him to understand where you’re coming from, and also understand where he’s coming from, we only see this relationship continuing in the same way it’s continuing. All this peripheral stuff: his friendship, his past actions, his stubborness, are all symptoms of larger issues going on for you and him. And in some ways you both seem like you’re struggling with some of the same things: self-worth and trust in other people.

Finally, sometimes relationships don’t work out simply because they are too hard. Meaning, sometimes there are so many things to deal with that the good times are constantly overshadowed by the weight of all the other issues. At some point you need to evaluate this relationship and decide if it’s going to work for you, and him. Love isn’t always enough. (And we hate to say that, because we believe in fairy tales as much as the next guy.)

Good luck. Please leave us a follow up comment, and/or question. And feel free to ask another question down the road.


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2 Comments on Boyfriend who has a history of doing unsavory things

  1. As I read this, I wonder why you hooked up with him in the first place, considering his unsavory past. Yes, Guys, people do change, but in my experience a zebra can’t change his stripes, especially zebras that like to cheat. My mom always used to say, ‘If he cheated on her, he’ll cheat on you.’

    The fact that he doesn’t defend you or your relationship to this ‘Diane’ but jumps on you every time you say anything about her is a big red flag to me. Yes, it’s ok to have friends of the opposite sex, but this particular friendship makes me want to scream, Run! Run away!

    Maybe you have a point with that, “Don’t I respect myself enough” bit. Do you have a history of relationships where men treat you poorly? If so, that may be something you want to examine in greater depth. I don’t know you, so I can’t say for sure, I’m just speaking from my own experience and track record with men.

    I really hope this all works out for you in the best possible way whether you stay with him or not. Just remember though, if you do stay with him, ‘Diane’ is not going anywhere and you will always have to deal with her.

  2. @Raven…thanks for your great insight. We appreciate the female’s perspective.

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