“My Boyfriend is Going on Vacation with His Ex!”

My boyfriend and I have been dating for almost six months and he has an ex with whom he shares a son who is almost 13. We plan on getting married, but we have a few things to work on…like boundaries with his ex.

They have been apart for ten years, but he still invites her on his family vacations and they planned a family vacation to the Bahamas this May. My boyfriend’s whole family is going — it is a 25-year anniversary party for his sister and brother-in-law. He did invite me to go, but I’m not able to. I have never met the ex. She calls constantly (not about the child), she posts messages and pictures on his Facebook, and she texts sometimes at 2-3 AM. My boyfriend does not see a problem with any of this. He tells me that he is not attracted to her and they are just friends.

They were planning on sharing a cabin together on the ship with their son and I said, no, he needed to get his own room.

I don’t think she should be going on family vacations with him and his family. She spends holidays with his family and travels to see my boyfriend’s sisters and brothers that are out of state.

I told my boyfriend that if he doesn’t tell her that she is uninvited on the cruise to the Bahamas, we are over. I think this is a deal-breaker. And I told him that he needs to set boundaries with her. He says he wants to talk to a counselor first before he makes any decisions on this. He also thinks that she may become vindictive and try to take him back to court for more child support. It sounds like he is scared of her.

We fight about this daily and need some advice. Please let me know what your thoughts are. Am I being totally ridiculous? I am also jealous she spends time with his family and I don’t. I think the family needs to set boundaries, top, when we get married…if we get married. — A Few Things to Work Out

Why on earth are you discussing marriage with a man you’ve been dating a handful of months and with whom you argue on a daily basis?! This is not anywhere close to the point you should be at in a relationship for marriage to be an appropriate next step… or even an appropriate topic of conversation. When people say they have a “few things to work on” before getting married, they might mean figuring out what kind of wedding they want or whether both parties agree on what house to live in; they don’t usually mean that “there’s another woman in the picture who calls all hours of the day and night, shares rooms with my boyfriend when they go on vacation together, and spends holidays with my future in-laws.”

Obviously, this goes well beyond having a few things to figure out. This is more like: Your guy really isn’t available to you in the way you want him to be. He’s still involved with another woman, whether he’s attracted to her or not. His life is very much intertwined with hers and you… well, maybe you’re the woman he has sex with, but you aren’t the woman he’s made, or is interested in making, a life with. You have A LOT to figure out before you even contemplate being serious with him, let alone marry him. And the truth is, the unorthodox arrangement your boyfriend has with his ex may simply work for them and they aren’t interested in changing it. I think your boyfriend’s hesitation to “set boundaries,” as you say, is a pretty strong indication of that and that you were right to set a deal-breaker for yourself. Now you need to be strong and hold to it and actually MOA if/when your deal is broken.

A few months ago, I started dating a really great guy. We were polar opposites, but I still found a way to “click” with no effort. I was the happiest I had been in a very long time; we had a great time together and we seldom fought.

About three weeks ago, he told me that he couldn’t be in a relationship because he had “a lot of personal things to figure out before he could love someone.” It was hard on me because it came out of left field. However, we decided to remain friends (as we had only been together a short while), and we still talked almost every day. When we did communicate, he was usually the one reaching out first. Recently, he has been reaching out more, and we just spent an entire day together jumping from one activity to the next (batting cages to drinks to dinner to driving around admiring beautiful homes). He made several comments about “doing this again,” and the entire day I felt like there was still something there between us. He’s also not the type of guy to play games or string me along. It didn’t seem like things were any different than when we were dating. I’m not sure if I can be misreading things. I have never stayed friends with an ex before; therefore, I don’t know if he’s just being friendly, versus pursuing me.

I just don’t know if I should say something to him or just see what happens? — Polar Opposites

The “personal things [he needs] to figure out before he [can] love someone” signify whether he’s ready to rule out sleeping with and dating multiple women. He realized you were getting close to being, or already at a point that you might like to be, exclusive and committed and he was not. Rather than “string you along,” he told you a half-truth — that he has things he has to figure out before he can be in a relationship. The rest of the truth is that now that he knows you aren’t expecting a commitment from him, he’s happy to keep dating you and maybe even being intimate if you’ll go there with him, but he’s also doing that with other women, too. If you’re cool with that, carry on. If you’re not, MOA.


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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. LW 1. I think you need to really think how you will fit into this family before making commitments. I know so many couples that are rethinking divorce and co-parenting. While the all hours texts might be something I would discuss. I know 4 divorced couples who do yearly vacations with the kids and sometimes new spouses. It is a way to show the kids that they are still a family even if the dynamics have changed. I know people that share holidays and birthdays and it is rarely easy. They do it because they both love their children.

    However, this would be very intense for a new person to enter into and I would think long and hard before committing. Because his ex wife and child are part of the package. I know if I didn’t have that kind of baggage, I wouldn’t do it.

    1. I’ll bet they don’t bunk together in the same ship’s cabin.

      1. Avatar photo Skyblossom says:

        Sharing a cabin would be too much for me. I think she should tell him it makes her very uncomfortable and see what he does without giving him an ultimatum. If he goes ahead and shares a cabin then the LW knows that they aren’t compatible and she moves on. If he decides to get his own cabin then they are fine.

        Dating is about seeing if you are a good fit and part of that is spending enough time together, by which I mean some years, to see if you match enough to have a happy marriage. If they fight daily they don’t appear to be a good fit.

        She needs to love him as he is or move on. She’s trying to change him into the man she wants him to be.

      2. SpaceySteph says:

        I agree that sharing a cabin is a bit much and it’s reasonable for her to express her discomfort and ask him to get his own room.
        But it’s often a lot more expensive on a cruise to get a separate cabin vs adding a third person to an existing cabin so they may have just been thinking economically, not like they want sexy times in a tiny room they are sharing with their son. (I just checked one cruise website for an example and it works out to $400 more to get a second room for a 4 night cruise!)

  2. My son’s father and I still take trips/vacations with our son. We have for 10+ years. I wouldn’t seriously date anyone who takes issue with it. It’s what we do. It’s our “family” time. It’s important to us. And there’s nothing inappropriate going on when it happens. We also text and call each other, often enough, that other people might think it’s odd…but I dare a significant other to tell me when and how often I can speak to my son’s father. I suppose, now that I’m thinking about it, that if it were JUST an ex, no kids involved, that might be different ??? I don’t know…..but as far as I’m concerned, my child and anything that concerns him, which would GREATLY include co-parenting, takes priority.

    1. The concern I would have with your situation is that you frame it as “our family time”. Your son’s husband is no longer your family. It is your son’s family time not yours.

      1. RedRoverRedRover says:

        A mother and father and son are a family. Sorry to break the news.

      2. dinoceros says:

        I think folks can determine on their own who is a part of their family. A person has a right to keep hanging with their ex if they want. People have a right to not want to date them, and I think that’s going to be a bigger hurdle for someone in that situation, but it’s their choice to be a family still.

      3. ele4phant says:

        The concern I would have with your situation is that you frame it as “our family time”. Your son’s husband is no longer your family. It is your son’s family time not yours.

        Nah man, I think you have a kid together, you are always family.

      4. SpaceySteph says:

        What ele4phant said!

        Whenever I see letters like this, all I can think is how lucky the kids are that their parents maintain a good co-parenting relationship and semblance of a nuclear family unit. Getting mom and dad on family vacations is awesome! LW can decide this set-up isn’t for her, but trying to break up this happy separated family is like the literal definition of homewrecker.

    2. carlos alberto says:

      totally agree with you

  3. for_cutie says:

    LW 1 & 2 MOA. Your boyfriends are not meeting your needs, and have both explicitly told you/showed you that they are not going to compromise on this. State plainly what you need and then walk away if you don’t get a clear answer AND follow through that meets your expectations, within a week.

  4. Avatar photo SavannahAnna says:

    Exactly! What for_cutie said. Especially LW1, you need to say what is a deal-breaker for you. Sounds like you’re there already, and your boyfriend doesn’t want things to change from what they are. He can say forthrightly how he thinks things should be, but he certainly doesn’t get to decide what YOUR deal-breakers are, come on! “He says he wants to talk to a counselor first before he makes any decisions on this.” Sounds like he has decided already, and this is not a negotiation where you deal away some of what is essential to you. Saying what you need in your life isn’t an ultimatum, and compromise isn’t splitting the baby in half!

  5. Skyblossom says:

    LW1 They have established their divorced relationship. You get to decide whether that relationship works for you but you don’t get to decide what their relationship looks like. You have no say in who his family invites on their vacation.

    My aunt and uncle divorced and kept getting together for Christmas every year and also sometimes other holidays like Thanksgiving. Their new partners were always invited. The holiday included everyone. My cousin now hosts an even larger holiday that includes her dad and his girlfriend, her mom’s husband and all of his kids and grandkids (her mom died ten years ago), her brother and his current girlfriend, her brother’s exwife and her boyfriend and their kids (the kids of her brother and his ex) and her own husband and their kids. It works for all of them.

    If that type of arrangement doesn’t work for you that is fine. You can and should walk away but don’t try to force his family to change. They will all resent you and it will become obvious that you aren’t a good fit for their family.

  6. In fact, LW1, he implied you are there for sex. Why would you try to set boundaries? You don’t really exist as a partner for him. Just go away of him.

  7. Northern Star says:

    LW #1, you’ve already identified your deal breaker. Is it reasonable? To me, yes. But the unreasonable thing is to expect your boyfriend and his whole family to change. They’re not going to. Or if they do, they’ll be resentful of you for shutting down their cozy relationship with the ex.

    MOA. Very few women will want to get involved with someone who bunks with his ex on vacation. But if he finds someone to tolerate it, hey, cool for him. Meanwhile, you can find a man who has healthy boundaries with his ex.

  8. LW1, it’s frankly absurd to think you can waltz into someone’s life and after six months, demand that they and their family change their relationships with people they’ve known for years before you came along.

    It’s even more ridiculous when the person you’re talking about is the mother of his child.

    You have every right to look at his closeness with his ex and say “hm, I don’t think this is going to work for me.” I’d be drawing a line at sharing a cabin, too, probably. But to demand that she be un-invited from a big family vacation? I’m sorry, but that’s just hilarious.

    If you don’t like the way he and his family are with his ex, by all means, break up with him. That’s absolutely your right.

  9. dinoceros says:

    I don’t think you’re wrong for being uncomfortable. I probably would be too. But I wouldn’t willingly get into a relationship with someone who has this sort of set-up with his ex, no matter how much it’s based on long-standing familial relationships or a desire to create normalcy for a child. Just not for me.

    But you don’t really get to dictate that he stop and change. And if this is such a big part of his life, it’s very unlikely he’s going to suddenly end it because you give him an ultimatum. (Him deciding on his own that he wanted to spend less time with his ex because of your relationship would have much more meaning.)

    Sounds like you two have very different ideas of how you want to live your lives. Might be best to find someone who doesn’t have the same sort of ties to their ex.

  10. Six months IS too early to get so serious. BUT I personally would not like this situation either. Too close for comfort to me!
    The “I think he is scared of her” is a giant red flag. I would rethink whether or not I wanted to be with a guy who was letting his ex push him around like that. If he wanted the situation the way it is, that is his prerogative, but to be forced into it by some psycho ex is different. The ex should NOT be calling all the time when it isn’t about the son. That is just weird.
    My husband has an ex wife he has a now grown son with. (I also have an ex husband and a grown child the same age. We would NEVER “co parent” like that) She attempted to have a similar situation with my husband and he wasn’t interested. When family asked why, he said he thought that was creepy and if he wanted to hang out with her, he wouldn’t have divorced her. They eventually started feeling like she was helicoptering and crowding her son. She tried for years. Did all sorts of annoying things, but he just completely ignored her unless it was something about his son. She called all the time. He would let her go to voicemail and then check the voicemail to see if it was about the son or not. She would even answer his son’s cell phone every time he tried to call him. (He has had his own cell phone since he was seven or eight) Interfered with their visits. She would come along every time he came up for a visit and stay at his mother’s. (while the boy visited us.) Irked him to no end, but she lives in another state, so she could only crowd him so much. The son is an adult now and the son (and his girlfriend) still live with her. She still answers his phone.
    She never dated again. Not in 13 years!
    I wonder does the boyfriend ever get to see his son one on one or does she tag along? They should have one on one time. No, this situation would be too much for me. I would MOA.
    She is probably not the only girlfriend or potential fiancé the ex has chased off.

  11. If the situation is not for you then don’t stay. I think the idea of keeping a family vacation is sweet and beneficial to the kid. I would side eye the room sharing but she is the mother of their grandson/nephew/cousin. . . She’s family. If they don’t mind her along then someone on the scene for 6 months has no business minding either. You were invited. It’s not their fault you can’t go.
    You cannot sign on to how he coparents and you are talking Marriage? He’s not for you. Find someone without kids or with the distant relationship with their ex that you seem to want. Don’t damage their family or his relationship with his kid because you have issues.

    1. Skyblossom says:

      There is no better way to make sure the entire extended family hates her than trying to tell them who their family is and who they can take on their vacation.

  12. Blended families are always gonna bring up these prickly issues. My cousin (male) recently had a baby shower for him and his wife thrown by his mom, and my uncles current wife was not invited. My mom thought it was in bad taste….I kinda felt for my cousin who lives far away from his mom, who maybe wanted to spend time with just her.

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