Dear Wendy
Dear Wendy

“My Boyfriend Just Broke Up With Me. Should I Pursue His (Former) Best Friend Now?”

My 2 1/2-year relationship with “Dan” ended about a month ago, we’ve had no contact since then, and I have no desire to get back together with Dan. My situation is a little odd, but I’ll try to keep it short: The entire time we were together, I was completely honest and vulnerable, fell in love gradually, and was very committed to a future together while Dan seemed to be very open and invested in the first one-and-a-half years we were together. I considered him my closest friend and soulmate. Then, he suddenly started ignoring me and treating me borderline cruelly for the last year or so. He also started isolating himself from all of his (and my) friends and not saying anything about what was going on. I did everything I could to understand what was happening (asking him, seeing a therapist, reading books, etc.), but he was no longer willing to talk to me or make an effort to stop hurting me while simultaneously stringing me along, telling me he loved me.

I tried to break up with Dan about six months ago after a particularly hurtful episode but then came back the next week because I still believed we could fix things. He started feeling more and more like a stranger to me. I felt miserable every day, and I started blaming myself. Eventually, I was able to open up to my friends and get some much-needed support. Dan broke up with me last month, saying that I couldn’t understand him, etc. I was completely devastated, but, with no contact, I’ve realized just how toxic our relationship was and how unhappy it was making me. It still hurts some days, but I feel ready to move past this now.

Meanwhile, I had a crush on his ex-best friend (XBF) before I met Dan. I pushed my attraction for XBF aside during my relationship, but since he and Dan were roommates I saw him frequently and we developed a platonic friendship. When the first breakup happened, XBF was there for me and held me, but I was still attached to Dan, so I tensed up and hurt his feelings. We’ve had a couple of other moments full of romantic tension that we’ve both kind of ignored. I liked him, but I was in love with Dan, and I’m not the kind of person to cheat. We’ve grown apart a little because of this, but we’re still good friends. With my new insights, I realize that I’ve had and still have feelings for XBF, but we’re graduating from college and he’s moving to a new state. I care about him a lot, but what can I do? — Scared To Lose Him

I don’t think you should do anything. In your toxic relationship, you sought support in books, friends, and even therapy, but you couldn’t actually end the relationship yourself despite how miserable you say you’d become. The relationship only ended when Dan broke up with you — just a month ago! — which you say “devastated” you. And now you’re talking about moving on, potentially with his ex-best friend who is moving away soon? Girl, no. This is not the time to be moving on with some other guy. This is the time to focus on yourself and find your footing again. A 2 1/2-year relationship at your age is nothing to sneeze about. That’s a significant time. And when almost half of that time was spent feeling miserable and confused, you need more than one month to process the ending — the ending of which you did not orchestrate — and the relationship’s impact on you.

In time, you may feel ready to date and you should. But my guess is that anything you pursue over the next couple of months is going to be nothing more than a rebound fling — a quick and easy way to boost your tarnished self-esteem and to help process the ending of your relationship. (There’s nothing like affirming for yourself the ending of something than to start something new, even if what’s new is just a fling.) I don’t think your ex-boyfriend’s ex-best friend is the right person with whom to explore this transition and your feelings around it. Too much history, baggage, and drama. Plus, as you say — he’s moving to a new state. What would be the point in even trying to start something romantic at this point?

I know you don’t want to “lose” XBF, but the only thing you have with him to lose is a budding friendship. THAT can continue. In fact, you have a much better chance of keeping him in your life if you avoid starting some sort of relationship with him at this point, when you’re still smarting from a breakup and he’s entering his own big life transition and moving away. Stay friends for now — keep in touch when he moves, and maybe in the future, when you’re both at different stages, the timing will work in your favor. But if you start something now, not only will timing and circumstances not be on your side, but you also are likely to ruin your friendship and any potential for something blossoming between you one day.

I caught my husband for the second period of time cheating on me with men off Craigslist. We have been married twenty-nine years and have three lovely children in their twenties. We have a lovely house and had a lovely life. We were both looking at retiring in one to two years. We spoke all the time of where we could move to and what fun adventures lay ahead. We are totally compatible in our interests and daily lives. We have good-paying jobs that we both enjoy. But about a week or so ago he asked me to pay a bill on his computer because he was out of town. When I pulled up the bookmarks to pay the bill, I saw not just AMEX, buand before and after lovely vacations. He was setting up encounters when we were watching movies and sporting events.

I first discovered this seven years ago. He got “help” then, and he swore this would never happen again. Our children were teenagers at the time, so it was more complicated to end our marriage then. I did give him another chance, but I made clear that the literature and research say this rarely works out. He swears he loves me and the life we had, but I kicked him out of the house. I know I need to file for divorce, but it’s tough making the final jump. Any thoughts? — Fool Me Twice

Ending a twenty-nine-year marriage is going to be hard. That doesn’t mean it’s the wrong decision…and it doesn’t mean you have to do it right away. I’d take my time with this, being gentle with myself while moving through the steps of grief. This is a loss much like any death. You’re losing a life companion as well as the promise of a future you imagined sharing together. Right on the eve of retiring and beginning what many consider the golden years of your life, you will have to re-imagine what those years will look like. The structure of your family has changed already just by your becoming an empty-nester, and now it will change further as you become single. It will take time — and support — to adjust to your new normal and to process all the mixed-emotions you must be feeling (and will continue to feel for some time).

If you aren’t already, I’d encourage you to seek some form of therapy. This is the time to call in support from friends and other family members. Now is a good time to start something new, too. Is there an activity or event you’ve always wanted to try or be part of? What are some things you told yourself you’d do once you had more time to pursue them? This is that time. This is YOUR time. You’re done raising your children, and you’re done fighting for a marriage that no longer serves you. It may be hard to see it this way, but this time for you is a gift. You have a chance now to re-imagine and create the life you want for yourself. And maybe that life still includes your husband in some way; maybe you two can be friends and travel companions. But I wouldn’t jump into that new relationship until you’ve processed the end of your current one, and that’s going to take time and some distance (and plenty of forgiveness). You might also decide you want nothing to do with your husband anymore, and that’s perfectly ok, too! The beauty of this period is that it’s about YOU and what you want and what best supports your needs.

In the meantime, do talk with a lawyer about how to get your ducks in a row and how best to protect yourself and your assets. You don’t need to file or sign anything until you feel ready to, but knowing what the legal path ahead looks like will help you on your emotional path forward, too.


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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.

40 comments… add one
  • Fyodor May 15, 2017, 9:48 am

    LW1,, I commend you on laying the groundwork for your next relationship before the old one was over. It’s the kind of advance thinking that many women don’t develop until they are older. Then they are left without a backup relationship when the first one ends. Congratulations on your maturity.

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    • Skyblossom May 15, 2017, 10:09 am

      You have to wonder if he was that stupid or if he wanted her to find everything and hoped she’d leave while he was gone, especially now that the kids are grown.

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      • Skyblossom May 15, 2017, 10:11 am

        This was meant to be a reply below.

  • Fyodor May 15, 2017, 9:50 am


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    • Cleopatra Jones May 15, 2017, 10:25 am

      Or better yet, don’t set up a bunch of Craigslist ads for indiscriminate sex with strangers.

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      • Fyodor May 15, 2017, 11:41 am

        Also good advice but much harder to make him into a good husband. Everyone can learn better infosec habits.

    • saneinca May 15, 2017, 11:27 pm

      Yeah and keep cheating on your wife.

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  • Bittergaymark May 15, 2017, 10:00 am

    LW1) Eh… Anybody eho CLAIMS their ex is “toxic” and then immediately vengefully plots to now go after their best friend the minute said relationship ends is more than just a little toxic themselves.
    LW2) This sucks. Sadly…. This is what happens when homophobia forces people to lie about who they are and what they really want. The good news is that thanks to our culture’s long fucked up history of this — you are so NOT alone. Join a support group and begin to sort out your feelings…
    PS — I gotta admit. I am curious… How was your sex life? Were there REALLY no indications anything was amiss prior to these instances?!

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    • Cleopatra Jones May 15, 2017, 10:09 am

      If they married relatively young then she probably doesn’t have anything to compare it too, so I could see her saying it was fine when in fact it was pretty dismal.

      Terrible sex in a marriage is always a recipe for infidelity (gay, straight or otherwise).

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  • Northern Star May 15, 2017, 11:03 am

    LW 2,Your future ex-husband exposed you to disease, and he lies to your face every day. He is a garden-variety habitual cheater, and he will continue to break his marriage vows over and over. You can’t trust him, which means you should not be legally bound to him. Maybe that will help you feel better about filing for divorce. You don’t have to be angry or bitter to take the next step—you simply have to believe that this man is an unsuitable spouse (which is certainly true).

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    • Bittergaymark May 15, 2017, 11:13 am

      Eh. Unless he actually HAS a disease, he has yet to expose her to one. Put her at risk — yes! But ease up on the non monogomy hysteria slut shaming, please! I still need to have my coffee…

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      • Northern Star May 15, 2017, 11:16 am

        *Shrug* We always say, “blame the one who made the vows.” He’s the one who made the vows. It’s ridiculous that you think it’s OK for a married man to be cruising Craigslist in search of random sex—especially after promising specifically NOT to do so.

      • RedRoverRedRover May 15, 2017, 11:17 am

        Whatever you think about monogamy, it’s super shitty to have sex with other people while presumably having unprotected sex with your partner. It should have been her choice whether or not to take that risk. He took the choice away from her. It’s not slut-shaming to point out he’s an asshole for doing that.

      • Dear Wendy May 15, 2017, 1:55 pm

        Well, geez, a cheater is exactly the kind of person who SHOULD be shamed! He IS a slut. Shame the bastard.

      • Suzy May 16, 2017, 10:26 pm

        Yes, I know have Type 1 and 2 of Herpes.

      • baccalieu May 18, 2017, 10:06 am

        Northern Star, you’re missing BGM’s point. He is not saying this guy did nothing wrong. He cheated, and perhaps worse, he lied to her about his sexual identity. But you led with “he exposed her to disease” not “he exposed her to the risk of disease”. Not every male engaged in homosexual activities is guaranteed to be riddled with disease. Granted that may have been a slip but, if so, it was a Freudian one. Also, you don’t know whether or not he used condoms and you don’t know whether there was penetration involved – it could have been just oral or even mutual masturbation, in which case the risk of disease is practically nil. I bet if the husband’s partners had been female you would not have laid so much emphasis on the “exposure to disease” (Ugh.) There was a whiff of homophobia in your comment, and BGM called you on it. You chose to interpret that as defending the guy rather than dealing with his point. Not to say that you are an out-and-out homophobe, but lots of people who are not have these lingering prejudices. You should own it and deal with it.
        Sorry, but I have to defend my “spirit animal”.

      • Kate May 18, 2017, 10:20 am

        Anytime someone cheats, the advice on here is their partner should get tested. Every. Time. This is not about homophobia.

      • baccalieu May 18, 2017, 12:11 pm

        She didn’t say go get tested (which would have excellent and practical advice for dealing with a small but not negligible risk). She said that the husband “had exposed [his wife] to disease” (with the disgust dripping off her words). She has only been exposed to disease if one of the husband’s partners does in fact have a disease. If I sit next to someone who obviously has a cold, I have been exposed to a disease. If I sit next to someone who shows no signs of illness, I may or may not have been exposed to a disease, since we can’t guarantee that that person is not sick. But we don’t know. The language that she used assumed that at least one of the husband’s partners had a disease. (and people on here have accused me of lacking in reading comprehension. That is what I am suggesting is the homophobic part. As I said that may have been a slip but if it was it was a Freudian one.
        Also, don’t you think that the fact that, as you say, Every. Time. Cheating. Comes up. Almost everyone has to mention that the person should get tested, usually as the first point, is a sign of slut-shaming (and in the case of homosexual cheating, homophobia). It’s as if everyone is saying “Before we get started here, let’s all remind ourselves that people who have sex outside a relationship and homosexuals are probably diseased.” “Yes, I agree.” “I agree, too.” The fact that it is a good idea makes it hard to dispute, so nobody usually does, but that doesn’t mean there isn’t an element of sex-negativity here amid all the pseudo-concern.

      • Kate May 18, 2017, 12:22 pm

        No, I don’t think it’s slut shaming or homophobia. I think it’s pretty common sense, if your partner was cheating with multiple randos off Craigslist, to go get tested.

    • ktfran May 18, 2017, 12:35 pm

      For the life of me, I don’t know how reminding someone to be careful with your health and get tested as soon as you find out your partner cheated is slut shaming or homophobic.

      Maybe the wording was slightly alarmist. But the sentiment isn’t wrong.

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  • Bittergaymark May 15, 2017, 11:37 am

    Assuming he had unsafe sex. I dunno. I suspect I’ve had sex with ALOT more men than this guy — and I’ve yet to ever contract an STD. (And yes, I do get regularly screened for them.). It’s called condoms and safe sex… something a good number of straight popping out babies everywhere LWs seem to have simply never have heard of…

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    • Northern Star May 15, 2017, 11:47 am

      Can you tell me how LW #2 is in the wrong here? Is she wrong to have three children? Or to expect her husband to NOT have sex with randos?

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    • RedRoverRedRover May 15, 2017, 12:12 pm

      It’s great that you’ve never had an STD. It doesn’t mean everyone is going to be as lucky. *Someone* is getting them, and it could very well be this woman’s husband. It’s one thing for you to choose to have sex and take the risk of an STD. It’s another thing for this guy to take the risk on behalf of himself AND his unwitting wife. How you can consider that to be slut-shaming is beyond me.

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    • dinoceros May 15, 2017, 3:59 pm

      Yeah. I think anyone cheated on needs to worry about it. I know people who slept with like 2 people ever and got an STD from one (while using a condom).

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  • Northern Star May 15, 2017, 11:49 am

    Are condoms 100-percent effective? Are gay or bisexual people allowed to have sex with whomever they want, whenever they want, regardless of marriage vows and promises to their spouses?

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    • Bittergaymark May 15, 2017, 12:56 pm

      Oh forget it. Learn to fucking read. I never said it was okay — I was suggesting that fueling the HYSTERIA that she now as an STD is rather foolish. Stupid. And ill advised.

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      • Northern Star May 15, 2017, 1:07 pm

        How is it hysteria, pray tell? I didn’t say she for sure HAD a disease. I said she was being exposed to disease. Which is absolutely true. And since her husband lies, there is no way to know if he had protected sex or not.

      • Kate May 15, 2017, 1:17 pm

        I would doubt they have sex anymore, given that she’s known for years he’s having a lot of sex with men and was never comfortable with it, and given that he’s probably gay, but it’s not unreasonable to think that a married man who has sex with lots of different randos who advertise on Craigslist for sex, and doesn’t ever clear his browser history, may not scrupulously use protection every time or make sure he and all his partners test clean.

      • bittergaymark May 15, 2017, 8:41 pm

        Like Kate, I doubt they have sex anymore. I dunno. The lack of mention of ANYTHING about their sex life made me suspect as much… If they had a slamming sex life, or even a normal sex life, I think she would have mentioned it. That she said nothing left me filling in the blank that THAT ship has sailed.

      • baccalieu May 18, 2017, 12:35 pm

        No it’s not absolutely true that she was exposed to disease. It is only true if in fact one of the husband’s partners had a disease. What is absolutely true is that there is a possibility that she may have been exposed to disease. You may think that this is only a difference in semantics, but I think that kicking it up a notch from “may possibly have been exposed” to “definitely has been exposed” suggests some underlying biases, especially since you don’t even seem to recognize the distinction. In neither case is the person guaranteed to get the disease, but one is a lot worse than the other. The fact that there is a small chance that the LW’s husband may have passed an STD on to her is really the least of her problems (and one that is easily dealt with by getting tested). It doesn’t deserve top-billing in everyone’s answer. Get tested, find out and move on. The fact that everyone is putting so much emphasis on it is the hysteria.

      • ele4phant May 18, 2017, 12:47 pm

        Eh – I dunno about this baccalieu, I do think you are arguing over semantics and the betrayal is just as bad.

        Sure, in epidemically terms, a cheated on woman (or man) is only exposed to disease if the interloping party actually had a STD that the cheating partner then catches, but regardless, the fact that the cheater didn’t use protection means they doesn’t CARE that their actions could’ve exposed their partner to a disease. The fact they have so little regard for their partner that willfully choose to gamble their health by not using condoms IS a big deal, and worth getting “hysterical” over.

  • Janelle May 15, 2017, 1:35 pm

    LW1: I don’t even get what you want to know? What do you do? Someone you aren’t realy talking to who is moving out of state you happen to like? And? Ok? I don’t even get what advice you are seeking.

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  • dinoceros May 15, 2017, 3:59 pm

    LW1: He’s moving to a different state. It’s not going to work. It’s one thing to be involved with someone and then have them move, but purposely going after someone who is moving away is not a good idea.

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  • Ashley May 15, 2017, 6:30 pm

    LW 1. Give yourself the gift of being alone. Cultivate your interests, learn what you like, what you don’t like. What do you value? Do you even know? It’s ok to be single for awhile. It’s nothing to be ashamed of, and considering what you’ve been through, it’s the smart thing to do.

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  • saneinca May 16, 2017, 12:48 am

    LW1, what you are feeling is called transference in psychology. You transfer your feelings and emotions to the next available person.

    Wait for a while, like 6 months and see if you still feel that way about the XBF. My guess is that you probably would have moved on.

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    • Ron May 16, 2017, 7:31 am

      With a dash of revenge thrown into the pot — not that Xbf will give a shit.

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  • Dear Wendy May 18, 2017, 9:44 am

    From the LW:

    I do actually agree with your advice. Graduation has been a really tough transition because most of my friends moving somewhere else to start their new lives is really scary. Plus, a lot of my friends who started dating around the time I started dating “Dan” are getting married this summer. I do feel really confused, both about what happened to our relationship, and about why it was so hard for me to leave even though I knew he had basically cut me out of his life without a word. Nothing makes sense: one moment he was introducing me to his mother and we were discussing our finances for when we got married, the next he was pretending our relationship had never existed. Even though we “got back together” about 6 months ago, I realized he’d been “gone” since our problems started a year ago and we’ve never fully reconnected, though we did have our moments. I’ve felt alone in this relationship for a while before our final breakup. I think most of my “devastation” came for blaming myself for something that was out of my control, as well as for staying so long.

    When I think about it, I don’t really feel ready to date yet, as much as I believe things could work between XBF and me. He’s one of my favorite people in the world, but you really don’t know how a relationship will work until you try. I’ve been close friends with XBF about 3 years, so I would hate to lose his friendship over a rebound fling. I didn’t say anything about my feelings, and we were able to enjoy spending a lot of time together before graduation, and he said we’d message (like we do every summer) and invited me to come visit him when I can. It’s funny, but although neither of us said anything, I noticed more physical contact and we felt closer these past two weeks before he left. Maybe things could work out one day.

    So, I guess for now I’ll keep on going to therapy and figure out what’s going on with me and what I’m doing career-wise, etc. and enjoy the friendship we do have. He’s still sorting things out too. And being betrayed by someone you thought was your best friend isn’t a walk in the park, either. It won’t be the same as when we lived in the same apartment complex, but he’s still XBF.

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    • Skyblossom May 18, 2017, 10:03 am

      Many of your friends who are getting married now that they are graduating college will be getting divorced in about eight years. In a few years some of those who are getting married now will envy you your freedom and wish they weren’t married and they will feel trapped. You are lucky to find out it didn’t work before you ended up married to the wrong person. College life is so different from work life that it is hard to tell how a person will fit into the real world and how they will handle it and what kind of a partner they will be.

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  • Leslie Joan May 23, 2017, 9:51 am

    LW, I can understand that you may be feeling gaslighted by your XBF, but the fact is that he may have been influenced by all the other people making marriage plans. It seems pretty clear from the outside that he really doesn’t want to do that with you, and he figured that by shutting you out and treating you like junk that you would dump him. Because you didn’t, he had to do the dirty work.

    I don’t mean to sound as though I’m minimizing your devastation; it’s hard to go from feeling like, “this is my best friend; we have a stable relationship; we’re planning a future.” But he’s going through changes and questioning the trajectory of his future, and he wants to pursue it with no attachments. I’m sorry, but in the end this will be better for you. You want to be with someone who wants wholeheartedly to be with you, not a reluctant participant. And it’s not unusual for people to want to be unattached in a time of uncertainty.

    One thing you wrote concerned me, LW, where you were concerned about hurting the XBF’s friend’s feelings when he hugged you, and you brushed him off. You owe this guy nothing. It’s perfectly reasonable to focus on your own feelings, within reason, when you are in a state of turmoil. Pushing him away could spare you from an additional level of turmoil, and I repeat, you owe him nothing, and you don’t need to pretzel yourself to please him.

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  • Lucas June 23, 2017, 10:56 am

    You should open up with XBF to know how he feels about you, and your friend, to find out what he thinks of this relationship and if it is possible to invest in it. If it is also his will, then talk to him to find a possible way to get together, since he is moving to try to move together or stay in the same place exploring the options.

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