“I Don’t Understand Why He’s Still Friends With His Ex-Wife And Why He Hasn’t Destroyed Her Photos”

I’ve been dating a divorced-with-no-children man for about a year. We are in our fifties. He hasn’t proposed yet, but we have been talking about our life “together” in the near future. He was married for fourteen years; she left him three years ago. I was married for thirteen years; I left him seven years ago.

[Supposedly] his ex initiated contact with him through text messages a little before we met, and she texts him every two to three weeks. He says they don’t talk about personal stuff, but, I wonder, what in the world divorcees with no children can talk about? And more questionably: Why is she contacting him when she is living with another man? When I asked him, he — rather passionately — said that he will be there any time she needs him. She was diagnosed with breast cancer and went through a mastectomy. He was crying when he told me the bad news; we prayed together for her. As a Christian woman I pray everyday for her; as his girlfriend I don’t see the logic of their keeping in touch when there is no reason to since they had no children.

I have researched online, and most divorce counselors and psychologists advice that the healthiest way to find closure after divorce is to cut ALL ties with your ex, unless there are children involved. I haven’t told him anything, but one day, when I stayed over, I was looking for socks in his drawers and found pictures of his ex. Why does he keep them? Does he look at them every now and then? I destroyed all the pictures of my ex, not out of anger but because that part of my life is over. When I mentioned that to him, he seemed confused and said that pictures are part of your history and should be kept.

Another thing that I think is not helpful in his getting finally over his ex is the fact that he keeps a very close friendship with his ex-sister-in-law. He says she is one of his best friends, she has been very good to him, and he will not be ungrateful to her only because her sister divorced him. This is not healthy because, every time he would visit his ex-SIL, undoubtedly all the memories – happy and sad – would come to the “front” of his mind, making it hard for him to once and for all “forget” his ex. He says they never talk about his ex, but I am not so sure about that, especially because of the cancer situation.

His ex-SIL invited us to dinner one day. She was polite and nice, but we didn’t talk much, and right after dinner she suggested we watch a movie. Where I come from, you NEVER watch TV with your guests; that is rude. I keep wondering why she did this.

He has told me I am the best lover – in all dimensions – he has ever had, and that he will never go back with his ex. I do believe him. Should I keep quiet and suffer in silence his relationship with both his ex and her sister? Should I have to accept he will forever be attached to them? Know(or understand) his friendship with his ex, but I will have to tolerate the friendship with his ex-SIL. Compromise. I guess that is one of the important keys for a successful relationship/partnership/marriage. — Not Into His Friendship With His Ex

What makes you think there’s only one correct way to divorce? Who are you to judge the way someone divorces? You think because he’s on friendly terms with his ex and that he didn’t destroy his photos of her tucked away in a drawer that he didn’t find “closure”? They’ve been divorced for three years! And who knows how long before that the marriage started falling apart. Maybe he got closure right away, which is why he’s able to be friends with her now and mean it when he says he’d never go back to her (which you say you believe). Maybe he cut ties long enough to heal and move to the next chapter. Maybe, after being family for fourteen years, he wasn’t willing to lose his former in-laws and, fortunately, everyone is ok with him remaining close to them. Everyone but you, that is.

Apparently, it eats you up thinking about your boyfriend being “attached” to his former in-laws in any way, and the idea of his discussing his ex-wife’s cancer with her sister? “Not healthy,” according to you. Not healthy to have all those memories of his marriage come flooding back every time he talks to his ex-SIL, because, of course, he’s unable to maintain any kind of conversation with this person he considers a “best friend,” without constantly thinking about his marriage. (Spoiler alert: People who actually have closure from their relationships and move on are more than capable of talking with someone who knows their ex or is even related to their ex without crashing out on memories of said ex; maybe YOU are the one who hasn’t gotten closure if you think such a thing is so far-fetched.)

And so, you both are faced with some decisions. You have to decide if his being on friendly terms with his ex-wife, and remaining close to his ex-SIL, is a deal-breaker for you. You say that, deep down, you know you will never accept or understand his friendship with his ex, so I would say that’s a deal-breaker. That’s your decision. You need to share that with your boyfriend, and then he needs to make a decision. He can either give up his friendship with his ex-wife and his relationship with his former in-laws, or he can give you up — a woman who thinks any relics of, or friendships fostered by, one’s personal romantic histories should be destroyed as if they never existed (and also that watching TV with one’s guests is uncouth).

I guess you’re about to find out just how great a lover he really thinks you are.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. You’ve got one option here, and that’s to break up with this guy and find someone who has zero contact with all of their exes and their families.

    You don’t get to come into a man’s life and decide who he can talk to and what they can talk about. Or what pictures of past events in his life that he’s allowed to keep. That’s absurd.

    You CAN decide that you don’t wish to date someone who keeps in touch with exes. That’s your choice, and your right. If it’s your dealbreaker, then end things when you find out that he maintains contact. But trying to ban existing friendships is just not going to work.

  2. I think it is fairly unreasonable for you to expect him to never speak to his ex or family after 14 years of marriage. It may not be your favorite thing but it sounds like she knows about you. Everyone has a past. It doesn’t die when yoh divorce. The fact that you distorted every memory of your entire marriage does read as though you have not moved on. Divorced or not I’d never destroy my wedding, vacation, etc. photos.

    My ex and I (not married) broke up 4 years ago after dating 10 years and we still talk often. We have a history, understanding and now a friendship. The relationship didn’t end because anyone did anything wrong but because we simply didn’t end up being right for each other.

    Your bf perhaps wasn’t meant to be with this woman forever but that doesn’t mean he hates her or she ceases to exist.

    I think it sounds like you may need to get over your marriage and insecurities in order to be in a healthy relationship.

  3. This comes up every now and then on this site, people that want to change their partner’s life and frienships with no reason at all but their own insecurities.
    LW, you have two options here: you either grow up and deal with this, or you decide that this is too much for you and you move on. You are not a supportive partner for your BF, a close person of his just had cancer and a major surgery that will scar her not only physically for life, and here you are making it all about yourself. Dude was crying when he told you the news and all you could think about was rude people asking you to watch tv with them (WTH is that about).
    Like Wendy said, people deal with divorces the way they want and you should be thanking the gods that your BF is a civil person that cares about someone he spent 14 (!) years with. That means he will probably care about you too. Oh, but I bet that is he was calling her “my crazy ass bitch of an ex” you’d be all over him.

  4. I’ve never been married, but I have pictures from my past with ex-boyfriends in boxes. Why? Because they were a part of my past. From time to time it’s fun to reminisce and remember things that happened. I’m even still friends with a few of them, after we cut contact for several months and got closure. One of us reached out for one reason or another and a friendship ensued. Do I think about how we dated every time I talk to them? No. Not at all. One of my ex boyfriends, probably my most serious relationship – I’m not friends with him and his new girlfriend.

    I don’t see what the big problem is? Why anyone would want to delete 14 years of history unless they were abused in some capacity.

  5. LW is yet another very unchristian who explains herself by proclaiming herself as a “Christian woman”.

    You are unreasonably jealous. I think what you really resent is that this guy had a married life before he met you and doesn’t view that marriage or his ex-wife in totally negative terms.

    Do this poor man a favor and MOA. You need to search for a 50-year old virgin Christian man. That should satisfy your particular needs.

    1. And wtf do you get off thinking you have the right to search his sock drawer. You are one very controlling, insecure,… I won’ t even type it.

    2. Juliecatharine says:

      This whole letter stinks of judgement and insanely controlling tendencies. LW, you sound nuts. Your boyfriend should run.

    3. thank you for saying this b/c I was nervous to write out “wow, a”christian” on a moral high horse judging others’ choices, what a shocker” but, seriously? You call yourself a christian and also a great lover; I thought extra-marital sex was considered uncouth by most christians?

      1. Juliecatharine says:

        Or for that matter divorce….

      2. artsygirl says:

        I was thinking that the cancer stricken ex wife probably finds a lot more comfort speaking with a friend and ex-partner over the daily prayers of a Christian woman who obviously resents her

  6. Another thing to remember…when you’re dating as an adult, people come with histories. And with years and years worth of people who are part of their lives. With friends and coworkers and exes and family members of exes and sometimes kids of their own, kids of friends or exes. Those relationships don’t come with an off-switch, and they’re not going to disappear because you arrived on the scene.

    Case in point: my longtime BF has been divorced for over 20 years, and has grown kids. Some of the kids share a house with his ex, so he sees her fairly regularly if he’s over visiting the kids. I know her, I see her at family events, we get along fine. My BF remained friends with her brother, who’s been terminally ill for awhile. Recently, it became clear that the brother was coming to the end of his life, and he was hospitalized in a nearby city. My BF offered to drive his ex and her sister to the city to see him.

    I get the feeling from your letter that you would have felt threatened by this. After all, they could have taken a train, gotten a cab, asked some family member to take them. That part of my BF’s life is over, right? What is he doing even staying friends with his former brother-in-law?

    I gotta tell you, I found out about this after it happened, and I thought my heart would burst with love. It was so typically him, and I loved him for it precisely because he didn’t have to do it. It was just the kind thing to do.

    1. dinoceros says:

      What a nice story. 🙂 The irony in the fact that Christianity seems to feature heavily in the LW’s relationship but she is so threatened by her boyfriend’s compassion in his ex’s time of need.

  7. Northern Star says:

    LW, I struggle with unreasonable jealousy. I know how it feels. And I know that it’s not my finest quality, so I have to combat it. And even with all that said—I would never tell my husband he can’t spend time with the family of his first wife. I join him, actually, and guess what? We spend time together talking about vacations and sports and events—not dwelling on the past.

    This is a deal breaker moment for both of you. If you want him to cut off his friends/family, there is no room for him to make a few changes to help you feel better. You’re skating perilously close to the edge here. You need to recognize that, and step back. Or if you can’t, let him go for both of your sakes.

  8. I guess you’re about to find out just how great of a lover he really thinks you are.

    Love it!

  9. Avatar photo Skyblossom says:

    The comments above touch on almost everything I would say. The one thing I haven’t see is about the photos.

    Even if he destroys the photos the life he lived for 14 years plus the years they were together dating will still have happened. It’s not like you can wipe them out by destroying them. They happened. He lived those years and they shaped him and are part of what made him who he is today.

    I consider the friendship with the SIL to be a good thing. It means he doesn’t hold the divorce against her. It means he valued the friendship enough to maintain it. Dropping the SIL from his life would still not wipe out the time he spent with his wife. This SIL even reached out to you in a friendly way and all you could do was condemn her. I assume you went to her home with the intent to find fault. I don’t know where you come from but I can tell you I’ve lived in four states in three regions of the country and never heard of that rule. How Christian is it to want him to break a friendship? Didn’t Jesus say that the greatest commandment was to love your neighbor as yourself? She is your neighbor. She is the person you are to love, along with the ex. Maybe you can learn kindness from your boyfriend. He sets a great example.

    The logic of staying in contact after a divorce even though they have no children is that they had an amicable enough divorce that they don’t hate each other. They had an amicable enough divorce to remain on speaking terms. It means they have managed to be friends in spite of a divorce. Some people realize that they aren’t good long term partners and divorce but never hit the stage of hating each other.

    1. It also means whatever happened between him and the ex was gracious enough that her family remains friendly. Also, the ex-SIL is including LW and that just strikes me as very welcoming

  10. My wife M is quite jealous and proprietary by nature. She had cause in the past because her ex before me cheated on her and used her. So when we got together, I cut way back on contact with the large group of female friends I had. i still have more female friends than male, which is likely somewhat unusual for a straight guy. I cut off all contact with my ex for a long while, but I also gradually intro’ed M to my women friends and some became our friends. Right now, my ex (same one from that era, because M and I have been together 28 years) is my Facebook friend, but we don’t really have anything to do with one another. The point of all this is that, like everyone else says, we all have a past, even those, like me, who have very few past relationships. Yes, i cut back and cocooned with M for a bit until she was feeling confident. But then she just had to deal with the fact that i have friends and that some of them are women. I’m on friendly terms with my ex. She is not relationship material and that is why our relationship ended many years ago and she is single by choice in her 50s. So, M could view our occasional contact as “trying to win me back” if it weren’t so ludicrous. She doesn’t bother because she has no cause not to trust me.

    LW, if you believe in your man, then cut this out and deal with your own issues. If you don’t believe in your relationship, end it. But don’t try to make someone behave the way you want to service your insecurity. That will never end well.

  11. artsygirl says:

    As soon as I read the [Supposedly] in the second paragraph I knew that the relationship is doomed. Nowhere in the letter do you give any reason why you would distrust the word of your BF, but it is apparent that you believe the worst of him and his ex.

    Also, the reason why so few people are able to maintain relationships with ex’s and their families is because it is HARD. Relationships end and even if it is not acrimonious, is easier to let those relationships fizzle out. It takes a lot of work to move past the hurt and disappointment to a place where you can be friends especially as each embarks on new relationships. Your BF sounds like a caring and supportive man. Do him a favor and break up with him.

    1. artsygirl says:

      Another quick point – Cut the sister in law some slack. It is entirely possible that she suggested watching a movie as a way to create common ground. There is a reason why movies are a popular first date since it gives two people that do not know each other that well something to talk about. She might have picked up on the fact that you do not want to hear about your BF, his ex wife, or their life together so this would have been a solution to make sure you were comfortable and the focus was on something banal.

      1. I generally don’t like putting the TV on with guests as I prefer to talk with them and get to know them so I can sort of see where this idea may have come from. That said I’m sure LW wasn’t the warmest beacon of guestly hospitality if this is how she writes about the poor SIL so no wonder the movie was flicked on, probably a respite.

  12. You sound like an absolute joy to be around – snooping thru his stuff (be honest, you weren’t looking for socks), judging one of his best friends for asking you to stay and watch a movie (I am quite curious as to where you are from – so I know never to go there) and showing ZERO compassion for a woman with cancer (but you pray for her daily – what a joke). No red flags for him at all, change nothing about yourself bc being the best lover he’s ever had is 100% enough to keep your relationship intact.

    1. Seriously? Seriously! says:

      Re: the sock drawer, that actually doesn’t strike me as the snooping type thing. “Accidentally reading his Facebook messages” — yes, but I’ve borrowed socks during winter from almost every boyfriend I can remember when my feet get cold. She clearly has a ton of insecurities and has unreasonable /skewed expectations, and I wouldn’t put it past her to snoop; just saying that isn’t a smoking gun (if someone else wrote in about finding their boyfriend’s cheating love letters in his sock drawer, I wouldn’t think –” snooper.” (FWIW I think it’s a little weirder to keep the pictures of your ex in your sock drawer, but that beside the point.)

      1. dinoceros says:

        Yeah, if you live with someone, I don’t find it that odd that you looked in a drawer that they use. Drawers are not super private. Snooping usually involves stuff like phones or email accounts because they have the expectation of being private. I’d like to meet the person who thinks, “I need to snoop in my partner’s stuff to find evidence. I should check out his sock drawer!”

  13. I suppose you want to know WHY WHY is he staying in touch with these people, and if I had to guess, it’s because it’s hard to find people who truly care about you sometimes in this world, and when we find them, we hold on to them.

  14. dinoceros says:

    If you consider being in a relationship with your boyfriend “suffering,” then leave. Nothing you described sounds too out of the ordinary or concerning. You didn’t list anything with YOUR relationship that was wrong, but instead listed all sorts of things that he is doing that you think is not being done the way it “should” be.

    Do a lot of people get divorced and hate their ex? Yep. Do some people not? Yep, that too. It’s OK that you destroyed photos of your ex and don’t talk to him. But your boyfriend isn’t you. He decided that she’s family and that he wants to be kind to her and stay friends.

    All in all, I think you’re unreasonable and rigid. The fact that in the middle of a letter supposedly about your relationship with your boyfriend, you stop to rant about how impolite his ex-SIL was to ask you to watch a movie (which pretty much everyone else does with their guest but you), makes you seem extremely critical and judgmental. Most people learn at some point in their adult lives that different people do things differently and that that’s OK. Sounds like you missed that lesson.

    I think you and your boyfriend should break up. It sounds like you’re not cool with how he chooses to live his life and you’re apparently “suffering” over it. Find someone who doesn’t have an exes.

  15. Bittergaymark says:

    This letter gave me a fucking headache. So much needless fucking bitchiness and all in the name of Jesus. WHATEVER! Fuck that. Oh, and LW? Fuck you…

  16. Morecoffeeplease says:

    LW, believe it or not there are people who get divorced and stay friends their whole lives! They even think of each other as family and their new significant others are brought in to the group. They are not jealous of each other, are friends, and simply wish each other well in life. This is normal and mature! It also is one of the best scenarios you can hope for after getting a divorce. I have met people like you…my own mom and my stepmom. They cannot stand this. They do not want to be around their ex. They seriously dislike each other and when forced to be in the same space completely avoid each other. This is immature. It shows how small they are. How petty. How jealous. And mostly, how insecure. If this is something you cannot stand please talk to your boyfriend about it and break up with him. Let him find a more open hearted woman.

  17. Avatar photo Skyblossom says:

    There is so much contempt in this letter. You feel superior in every way. You have the best and only acceptable way of getting over an ex. You know better than he does how he should live his life. You know better than he does whether he should have old photos. You know better than he does who he should have as friends. You don’t believe what he tells you or you wouldn’t write supposedly in the second paragraph. At the same time that you feel contempt because you think he isn’t honest you feel free to search through his sock drawer. He’s open about his friendships and relationships and past. You sneak around in his home spying on him and then call it looking for some socks. Whose the honest, above board one in this relationship? I don’t think it is you.

  18. Of course he’s lying to her. He say’s she’s the best lover, ever. He knows she needs to be jollied along and appeased, in order to keep any sort of peace. She is a difficult person and he has made some adjustments for that, but he won’t dump his friends. She demands full out surrender of his essential shelf. Don’t do it man!

    1. I bought an elliptical machine recently because my wife demands I surrender my essential shelf.

  19. Bittergaymark says:

    PS — suffer in silence?! This LW strikes me as a particularly LOUD sufferer…

  20. Findingtheearth says:

    I’m low key curious why he should have to cut her out of his life? Not all marriages end badly and perhaps they’ve worked out whatever grudges they had.

  21. Findingtheearth says:

    And you are asking him to cut her out of his life when she has cancer? That is just beyond cruel.

  22. You can’t just cut out all those years. It’s probably best to just move on, if your having these problems now I can’t image how it will work if you stay together.

    It’s a poisoned situation that will just grow into something truly ugly down the road, and end in another divorce. The only good thing is that there are no children involved.

  23. Avatar photo Dear Wendy says:

    From the LW:

    I have been praying for the last two days and nights reflecting on the realistic [albeit harsh] words from you and your readers.
    Yours and your readers’ replies -although delivered in a mean manner- are right. I realized we all sometimes need to be shaken to wake up from our formed-from-wrong-concepts fantasies to be able to embrace the love-giving reality we are called to live.

    All of the websites I found about divorce recommend that the healthiest way of dealing with it is to cut all ties with the ex -if no children are involved- to attain closure and be able to get over the breakup and move on, especially if you were not the one wanting the divorce. That was the premise I based my way of thinking, but I wanted to hear from real divorcees and that is what I found here.

    Wishing you and your readers the best.

    Striving To Improve

  24. Wow! You guys are all patiently accepting of your partner being friends with ex partners then? I don’t believe that for a second. This lady has trust issues and that’s agreed, but I’m sorry, they are exes for a reason and once they’ve gone, they’ve gone. There is always something there after a relationship ends, and my current partner is more important than a past relationship. You can’t have it all your own way in a relationship, sacrifices have to be made.. I would leave the relationship, he sounds like he isn’t over the situation. It’s a major red flag. Leave and find someone who is truly over their past.

    1. Actually, there is NOT always “something there” after a relationship ends. Sometimes, a relationship has run its course, you realize you’re no longer a good fit and you break up amicably. In those cases, there can definitely be a friendship or fond memories that you don’t want to lose.

      I’m pretty sure I have some photos of past relationships lying around our house somewhere. I’m certainly not pining over my ex’s. They’re good memories of fun times I once had in interesting places and they’re a part of me. If my husband asked me to throw them away (which he wouldn’t, because he’s not insecure), I’d tell him to get bent.

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