“Should I Cut Ties With the Man of My Dreams?”

Nearly three years ago, I divorced the man I’d been with for over ten years. The very next night at a party I met what was supposed to simply be a rebound. On our third date, as I was trying to figure how to tell him I was going through a divorce, he dropped a bomb on me: he was going through a divorce as well. Great! Neither of us is emotionally available so no one can get hurt here, right?

In typical rebound fashion, things moved very fast, but I’d never met anyone like this guy. Within our four-month relationship, we were together nearly every day, and we saw each other through some of the roughest emotional parts of divorce. I practically moved in with this guy, who’d moved back home with his parents to regroup. I met his parents and siblings, and they all kinda adopted me when I needed people the most. I had a family to have dinner and make s’mores with and to drink beer and tell jokes with, and I had a guy I was becoming very fond of. (My own family moved to another state ten years ago and hasn’t been back to visit since; we were pretty dysfunctional and were never all that close anyway).

As I realized I was catching serious feels for this guy, I knew it would only lead to more heartache, plus I hadn’t even dealt with the pain of my divorce yet. I decided to end it before I ended up the Transitional Relationship girlfriend that ended up heartbroken once he felt better. We liked each other very much though, so we agreed to stay friends (after a 60-day, no-contact period that I asked for) and said we’d like to revisit our relationship in several years after what I could only hope would be some serious healing.

It’s now almost three years later, and we still talk nearly every day. I’ve remained single, dating one or two guys here and there, while he had a steady girlfriend just about this whole time (he fairly recently broke it off). We never really stopped seeing one another though except for that 60-day break; we went back to doing all the fun things we’d done before like concerts, drinks, dinner, the beach, lunch, etc. I can admit now I pretty much started seeing this guy again while he had a girlfriend, and, of course, eventually we started sleeping together again. Before I knew it, I was back hanging out with him and the family who missed me and adores me (as I do them) like he hadn’t been seeing another girl for over a year. I managed to never cross paths with her, and I’m not proud of the cheating part, but I’d be lying if I said I felt guilty about it. I believe we genuinely care for one another, but the timing is just wrong.

I’m still a bit raw emotionally, but I think that, because of our history, I feel bonded to this guy. Not to mention the whole great family thing. He tells me his parents speak of me all the time, as though I’m just on away on a trip, and that they are hoping we pair up again once I move back home. I moved out of state for a little while to finish school, but, like I said, we still talk everyday, sometimes more. Now that he’s single again, whenever I’m in town, it’s like I never left; we go back to hanging out at cool shows, hooking up, and playing house. It’s . . . weird.

I guess I’m wondering if I need to sever ties completely, or just be okay with this sort of back-burner relationship. I mean, it’s never easy talking to him about a guy I met, or hearing about a girl he met, even though neither of us seems to want to be with the other seriously now (nor can we with me in another state for another year). I finally feel ready for my own transitional relationship, and, even though I’m not looking for marriage or anything, I really want to get it right and be in something healthy; I’m not out to hurt anyone. I don’t want to lose the people I really consider my friends, either. What would you do? — Ready for My Transitional Relationship

Oh, good grief! Do you want to be with this guy or not? If so, just be with him! All this talk about not being emotionally ready or living too far apart or needing a transitional relationship first or whatever other excuse you’ve come up with is just BS to cover up the fact that YOU’RE SCARED. Divorce sucks, I get it, and it left you reeling. You don’t want to go through that again. But what you’re doing now? This limbo thing you’ve got going on? It’s not going to save you from ever feeling hurt again. It’s only keeping you from feeling fulfilled. It’s only prolonging this “transitional” period you have been insistent on having for three years since your divorce.

Decide whether you truly want to give a relationship with this guy a shot, not because you adore his family but because you adore HIM. If the answer is yes — yes, because you can’t imagine losing him (which is what will likely happen if you continue playing this game you’ve been playing with him for three years) — then act fast. Be proactive, be brave, and take a risk on love. All the details, like your not being in the same state for another year, will work themselves out. And if they don’t? Well, then you will have had that “transitional relationship” you’ve been telling yourself you need before the real deal. But, girl, maybe this IS the real deal. In which case, stop trying to fuck it up.


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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. Avatar photo Addie Pray says:

    Yes yes for the love of God yes, what Wendy said. In all of this I heard nothing wrong with the guy. He seems to be the full package – lover and friend, with a good family that adores you, plus he’s respectful of all the boundaries you are laying around – though like Wendy said I think risk losing him if you don’t jump in soon…. Move back, make it official, throw caution to the wind, love is all you need, love lifts us up where we belong!! Rejoice!!!!!

    1. RedroverRedrover says:

      He did cheat on his girlfriend with her for what sounds like a really long time. If I’m reading it right, he was sleeping with the LW for basically his whole relationship with his girlfriend.

      1. Avatar photo Addie Pray says:

        oh yeah that wasn’t good.

    2. AP and BF sitting in a tree, K-I-S-S-I-N-G!
      First comes love.
      Then comes marriage.
      You know the rest…..

      1. Avatar photo Addie Pray says:

        No, “then comes a pre-nup” needs to be in there. Hahaha, kidding.

  2. RedroverRedrover says:

    I had a “friend” like this for like 5 years. Basically I wasted the best part of my 20s on him. Honestly, if you think it’s a problem of timing, you’re wrong. If someone wants to be with you, they’ll be with you. If they don’t want to date someone else, they won’t date someone else. If you’re in this kind of limbo relationship, it’s because at least one of you doesn’t want a real relationship. Maybe it’s you, maybe it’s him, maybe it’s both. But you should either turn it into a real relationship, or break it off completely, because right now you’re just sitting in neutral, wasting time that you could actually be meeting a real partner. Will you be happy 5 years down the road if it’s still like this?

    1. RedroverRedrover says:

      Also why would you want to be with a guy who would cheat on his girlfriend for so long? And he didn’t even break up with her for YOU. If he wanted to be with you, why would he stay with her? He clearly knew he could have you, and still chose to just sleep with you on the side and keep her as his official girlfriend. I mean, sorry, but it’s not looking good. I don’t want to sound mean, and I would have hated it if someone talked to me like this when I was in my similar situation, but I think it’s true in this case.

      1. Avatar photo muchachaenlaventana says:

        I agree. If he wanted to be with her so badly, why would he have just cheated on his real girlfriend for their entire length of the relationship..I mean why wouldn’t he just have broken up with her. And how is the LW okay with this? It does not indicate someone of a high moral caliber to me.

  3. Oh for the love of god, I can’t handle this today. LW, “timelines” and what people are “suppose” to do are the most ridiculous thing ever. EVER.
    No, you don’t need to be married and have 2.5 kids by the time you’re 35, for example. And no, you don’t need to have a transitional relationship. People say these things so they can feel in control. Do what makes you happy or fulfills you in your own time and fuck what books and the internet say, and people who judge, within reason of course. If you’re doing something that hurts yourself or others, then listen to those smarter than you or people who have their shit together. Like people on DW.
    Also, this “you” iI speak of in the previous paragraph is not the LW, but folks in general.

    1. Avatar photo Addie Pray says:

      But don’t just fuck what the internet says when it’s said on DW, duh. (ktfran, watch yo self!)

      1. I put a disclaimer about that!!!!!!!

      2. Maybe in that disclaimer, I should have added “when you’re being ridiculous, listen to DW.” I thought that was covered under harming yourself, but I should have been more explicit. I apologize for not being clear.

      3. Avatar photo Addie Pray says:

        To the time out chair you go, haha.

    2. I really wonder why anyone would want a transitional relationship. I mean I get rebounds, but why have a real relationship that you anticipate from the beginning will end in heartbreak?

      1. Hahaha. When you put it that way, it sounds even worse! And you’re correct. Any relationship I enter, I’m not looking for the exit. Just, why?

  4. I 100% agree with Wendy’s advice – take the risk and tell this guy you want to be with him for real, if that’s what you want. However, I also suspect that there’s a reason this has been a ‘backburner’ relationships for so long and that it won’t work out. But you’ll only know for sure if you ask him. The one thing I keep asking myself is why the hell you believe there’s less emotional risk involved in ‘playing house’ and hooking up with a guy you’re not with for years compared to just trying for a real relationship. It sounds like you’re getting all the bad stuff from being in a relationship (like not being able to date anyone else seriously) and none of the good stuff, like actually being with someone you love. So I’m seriously confused.

  5. Yeah, I’ve been worried about the whole scenario for me and M, too. Like, we never really dated, and since we had both not had any other relationships since our previous breakups, we are technically still a transitional relationship. Also, we never really dated like you’re supposed to. We just starting hanging out and having sex and then without even considering strategy, a few years later, we up and got married. But now I’m worried that 25 years later, this is just the mother of all transitional relationships. I mean, we were sort of “friend-friends” before we hooked up, so i’m concerned we may be screwing up that friendship by being in this transitional thing. And when it ends, we’re just going to be heartbroken again. So now we’re kind of stuck in this happy marriage that is really just a rebound thing. It’s like some kind of destiny-type thing. Makes you think.

    1. Avatar photo veracityb says:

      Ha, got me logging in just to upthumb this.

    2. Well played. You win. Hands down.

      1. Hands down is how this whole thing got started. We had some drinks, she put her hands down, I put my hands down…

  6. TheRascal says:

    Can someone please define “transitional relationship” for me? I don’t know what that means.

    1. Avatar photo Addie Pray says:

      All my relationships until now have been transitional in a sense.

      1. TheRascal says:

        Seems like all relationships that end could be “transitional” post-mortem, true, but what does it mean for one to enter a new relationship thinking, “well, this is just a transitional relationship.” What does it mean in that context?!

      2. Avatar photo JenjaRose says:

        It means that she is absolutely terrified of the risk of “failure” and heartbreak involved in a real relationship, so she’s not even going to make the effort or emotional investment, thus dooming every relationship from the beginning.

        Some folks, eh? ¯\_(ツ)_/¯

      3. Avatar photo Addie Pray says:

        beats me.

  7. bostonpupgal says:

    So I agree with everything Wendy said, but I just have to add…this guy cheated on his serious girlfriend with you for basically their entire relationship. Now that the poor woman has wised up and finally split you can admit your part in it, but you feel absolutely no remorse. Wow…that is just disgusting all around. I’d be having second thoughts about keeping a man in my life who would betray someone like that if I were you, too. It sounds like you two deserve each other tho, so I say go for it and try for a relationship.

  8. snow.angel says:

    I totally understand not wanting to move too fast or get too invested in a rebound relationship right away after a divorce, but I think your relationship with this guy is way past all of those concerns. I mean, it’s been three whole years! I think if after three years, you still have such a strong connection and attraction to someone you can safely move them out of the rebound category and start to see them as someone you are genuinely compatible with. I can’t even imagine how scary it must be to try to commit to someone again after a divorce, but it sounds like this guy is a great match for you and it’s time for you to go all in and see where it goes. While all the planning, timelines, etc. are probably great for helping ease your nervousness about having a serious relationship with this guy, the fact is even if you do everything “right” by these imaginary standards you’ve created, the relationship could still end for any number of reasons. Or, you guys will be incredibly happy and spend the rest of your lives together. You’ll never know unless you give a relationship with him a real chance, but I agree with Wendy that you need to communicate with him about it very soon so that you don’t lose him.

  9. Avatar photo JenjaRose says:

    Sooooo, LW, you’re just gonna ignore the fact that this guy is a cheater? :-/

    If you two actually get together for real, can you trust him while you’re out of state? Or even when you are in the same state, like he was with his STEADY GIRLFRIEND of apparently THREE YEARS that he was CHEATING on with YOU? Are we just ignoring this? There’s no way that I, personally, could trust someone who is a proven cheat. He turned you into the “other woman” and you went along with it as though it were all you deserved as a recently divorced woman. Why would he keep sleeping with and basically dating you while he is in a steady relationship with someone else? If you were so special to each other, why wouldn’t he just be with you and only you? If he loved you and wanted you and, clearly, could have you, why was he with someone else all that time? This whole thing is stupid.

    End this silly game one way or the other. There are absolutely no rulebooks or timetables about relationships. You don’t need to wait a specific amount of time or date a specific amount of people before you are allowed to be with the person you love and be happy, for crying out loud! Lay all your cards on the table. If he doesn’t want to be with you and only you, then you should cut him out of your life and open yourself up to someone who give you all the love and commitment that a real, healthy relationship requires (and don’t treat it half-heartedly as “temporary” or “transitional” just because you think that’s required of a divorced woman for some ridiculous reason!) If he does want to be with you, enjoy it and demand (and give) real commitment. No more of this wishy-washy bullcrap. Work out the long-distance issue (and have a conversation with him about what fidelity means to you!) Be 100% in or 100% out.

  10. You want him then date him. You don’t want him then date someone else. Just don’t expect him to come running when you decide you did want him after all. He may have cheated on the ex girlfriend with you but he may meet and fall for a girl he would drop you for in a hot minute. It’s about risk and opportunity costs…and reward. And you need to lose the stupid rules you have in your head about what happens when and with whom for how long. That’s not how life works and you could miss out on something great because it didn’t fit in with your self imposed timeline.

  11. Yeah I get not wanting to jump in too fast…but you ALREADY DID THAT. You jumped into a relationship with him the same day as you decided to get divorced. So that excuse is kind of null and void isn’t it?
    Look, in my opinion you’re putting this guy on this massive pedestal. It feels so awesome and great because you got out of what sounds like not the best marriage and he was there. And if you’ve spent long enough in a relationship where you’re truly not happy, the next relationship with ANYONE who is even remotely a decent human being is going to look and feel awesome. So you’re thinking “he’s so great and so perfect!” because of that. Yet at the same time, you’re ignoring the “oh, he cheated on his girlfriend with me and isn’t making any effort to be with me so maybe this isn’t the best of ideas”.
    If you haven’t gotten together with him yet after 3 YEARS quite frankly I doubt you will EVER get together.

    1. RedroverRedrover says:

      Sounds like she’s super attached to his family. Maybe that’s one of the main attractions. She says how they were basically her support group as she was going through her divorce. She should just stop sleeping with the guy, become friends, and keep hanging out with the family, if that’s what she really wants. They’ve been “friends” long enough that they don’t have to be in a relationship for her to love his family.

  12. Eh, I don’t think she should shoulder blame for the cheating. I don’t recommend cheating… But I’m guilty of it. It happened, and I do feel bad. But my ex was nuts and I’m in love. It’s his problem, not hers. As for actual advice, wees. Either go for it, or stop playing with him.

  13. Avatar photo possumgirl says:

    DO IT, DO IT, DO IT! GO GET HIM. If you love him this much, TRY. Otherwise no matter who you date, you will always wonder about him. If it doesn’t work out, you will at least know that it wasn’t right and will find happiness with someone else you blend with. If it DOES work out, you will have the man you love intensely and completely.

    Maybe I’m projecting because I had a similar experience. I’m so glad that I made the decision make the leap with my bf. We’ve been going strong (legitimately) for two years. I have never known love, happiness and true connectedness like I do now. It’s amazing.


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