Dear Wendy
Dear Wendy

“My Boyfriend is Going on a Pre-Planned Vacation with His Ex-Girlfriend”

I’ve been dating this guy for about six months. When we met, he let me know that he and his girlfriend of several years were on a break. We have had an amazing time together, with tons of laughter and shared interests and even a bunch of amazing weekend trips to ski or hang in the city. About eight weeks into this he let me know he had booked a trip to Asia for two weeks, planned a year ago, with a group of friends, including his ex.

Things got more serious with us leading up to that scheduled trip, and as the time got closer, he would tell me planned trip details while I expressed that I did not want to hear them. Eventually I realized I had strong feelings and that I could not continue this relationship knowing he would be traveling with his ex. I should also mention that, in addition to being on this trip, she was all over his social media and he admitted he still had feelings for her that were unresolved in spite of his falling for me.

We are both in our late 30s, but I’m not in a race to settle down and I am certainly not in a place where I am willing to settle. I told him I was done and that I felt that the whole situation was too much for me. He has since written me a letter expressing he is in love with me — yet still planning on heading on the trip. I am feeling a bit out of sorts here, not sure if I am blowing up something potentially amazing due to timing. Thoughts? — They Were On a Break

I think you did the right thing breaking up with a man who still has feelings for an ex he’s about to travel to another country with for two weeks. I would go a step further if I were you and tell him that you need him to completely leave you alone — no texts, emails, social media messages, phone calls, anything. You want a clean break because it was hard enough falling for someone who still has feelings for someone else and you don’t want to drag yourself through whatever trip he’s on — metaphorically speaking — with his confusion about where his heart is. Stand your ground, girl. A man who was truly in love with you would not risk what he had with you for a vacation. He’s playing you. He’s probably playing his ex, too, but that’s her problem. Let him go, and in the future don’t date someone who is “on break” from someone else. Any break-ups have to be clean, official, confirmed break-ups or you’re not putting your heart on the line, period. Since there’s enough risk in general for heartache whenever you date anyone, why add even more risk by dating someone who is still admittedly attached to someone else?

I met this amazing girl, a one-in-a-million sort; we got along from the word go and everything felt like it was falling into place perfectly. She was the first to say “I love you,” and after roughly three months together, as far as I was aware, we were still getting along like two peas in a pod.

I’ll admit I was a little insecure about certain things (her exes and some of her close guy friends), but I never stopped her from doing anything she wanted to do; it was just nice to have a little reassurance every now and then.

Her mom suffers from health issues, is wheelchair-bound, and is frequently in and out of hospitals. With stress over her mom’s health, over the fact she has had to move in with one of her friends as a boarder because she can’t afford to rent on her own, and over a legal thing going on with her brother that I won’t go into detail about, she has decided that a relationship with someone who she felt needed constant reassurance was just too much to deal with, so she ended up calling it quits with me.

She told me that she still loves me and cares for me, but that she just has so much going on right now that she feels overwhelmed. (She also always suffers from severe depression at the best of times.) All her friends love me, and one of her closest friends has even said that we’ll get back together but that it’s just going to take some time.

I still hang out with her friends when she’s not around, they’re really cool people, and the other day my ex called my mom up in tears telling her that she loves me but that she just can’t be with me right now and that she’s sorry for hurting me.

What do I make of all this? I know it’s an early relationship, but I’ve honestly never felt this strongly about anyone in my life. I’ll wait as long as it takes, but am I just setting myself up for disappointment? Will she actually come back? — Set Up for Disappointment?

Even if it’s not disappointment you’re setting yourself up for, it’s stress, turmoil, and a whole lotta drama. Look at all the drama after only three months! And if she “suffers from severe depression at the best of times,” she is not anywhere close to ready for a relationship, let alone a relationship with someone who sounds as emotionally… well, needy, as you do. Please, for your benefit as well as her benefit, shelve any idea of a romantic relationship with this girl. If you think you could be her friend with zero strings attached, fine, but I have doubts that that would be possible. Probably better to simply cut ties with her, wish her well, and move on. And that means stop hanging with her friends, too. She was honest with you when she said she doesn’t have the emotional reserve to tend to your needs or the demands of a relationship. Respect that and move on.

My boyfriend has a card that his ex-wife gave him in the dresser by the bed. He also has, in the cabinet, a bottle of champagne from their wedding, and, in the drawer in the bathroom where his shavers are, a picture of him, her, and his parents. What does this mean? — The New Girlfriend

That he either is very lazy about de-cluttering or is still pretty sentimental and nostalgic about his ex-wife and their marriage. Unfortunately, I can’t tell you what the correct answer is here. The only one who can help you figure it out is your boyfriend, and it sounds like it’s time to have an uncomfortable conversation with him. Be sure to address your feelings about seeing these mementos of his past relationships so easily accessible in his home. His response to you will tell you a lot about where his heart is.


Follow along on Facebook, and Instagram.

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

15 comments… add one
  • moe March 9, 2018, 9:52 am

    #1: I think that it was a huge red flag when you started dating that he said he and his girlfriend were “on a break”. That was him telling you that he was expecting that they would get back together and that you were a temporary distraction.
    #3: I keep my erring from my marriage that ended 7 years ago on a shelf above my bed. I have never for one moment felt I wanted to be back with her or harbor secret feelings for her. It is just nice to keep some memories of my life around me. If someone’s entire house is a shrine to an old relationship, that might be bad, but I don’t think a few items necessarily means much.

    Reply Link
  • Avatar photo

    Skyblossom March 9, 2018, 9:58 am

    A picture in a drawer with shavers is a picture that has been dumped there from somewhere more important.

    Reply Link
  • SpaceySteph March 9, 2018, 11:18 am

    I think Wendy’s right that its good that you guys broke up because he’s obviously still hung up on his ex and admitted it to you directly, BUT I’m not sure that I think the vacation is that much of a red flag if it were happening without other signs. A trip to Asia is not a small thing. It takes a lot of planning and a lot of money, probably of the non-refundable kind. I mean they’ve been planning this thing for a year, that’s a huge investment to just cancel. Plus its a group thing with a bunch of his buddies, not like they’re going on a romantic vacation just the two of them.
    I still think breaking up was the right thing, because he told you he still has feelings for his ex and he thought they were “on a break” when you started dating which is even worse than just being the rebound girl. The vacation is just the cherry on top of a not-over-her sundae.

    Reply Link
    • Rangerchic March 9, 2018, 11:25 am

      I agree, especially about the trip. It’s not like it was a trip to Vegas or something where if you did cancel you’ll probably loose money but not nearly as much as a trip to Asia. Most trips are non-refundable anymore (unless you purchase the insurance maybe).

      Reply Link
    • csp March 9, 2018, 11:46 am

      Totally Agree. the trip is a cherry. The “On a Break” “Still have feelings” is the killer. Let him deal with that before working with you. You do not need to be strung along.

      Reply Link
  • Fyodor March 9, 2018, 11:31 am

    RE LW3, I don’t get the issue with the picture in the drawer. It’s in a drawer. And even the champagne-should he have poured it out? I could see not really knowing what to do with it in his situation. It’s not like people really declutter their wine racks.

    The card I…guest is something, but unless there is some pattern of inappropriate contact with her it seems like a thin reed to get upset about.

    Reply Link
  • Northern Star March 9, 2018, 11:33 am

    LW 1: You were a placeholder. Breaking it off once you found yourself wanting to be more than a placeholder was the right choice. Stand by it. If you want a committed, loving relationship, don’t date people who are still with other romantic partners.

    LW 2: Leave the girl alone for now. Work on yourself so you can be a confident, strong partner in future, whether that’s with her or someone else.

    LW 3: How do you know the champagne is from his wedding? He must have told you—and that would have been the perfect time to ask why he is hanging on to it. Next time you’re rummaging around in the cabinet looking for wine for dinner, bring it up.

    Reply Link
  • csp March 9, 2018, 11:51 am

    LW3 – I think these things are yellow flags, not red flags. I would note them but not worry too much about them. You didn’t give major information like how old you are, how long they were married, and how long he has been divorced. These all matter. But the thing is, when you are in a long term relationship like a marriage, there is a history there. That isn’t erased when you divorce. I could see keeping pictures and mementos because it is the story of my life. Honestly, I don’t think that is very many things at all considering he was married.

    Reply Link
    • SpaceySteph March 9, 2018, 11:59 am

      I only have one really serious ex and we were only together for 2 years but even we had experiences and trips that I don’t totally hate remembering. You don’t purge your life experiences just because you break up. I wonder what the picture is of. If its just a portrait or a wedding photo that might be a little odd (though not a big deal on its own) but if they’re in front of the Eiffel Tower or something, well then its not just a memory of his ex and her family, but of a cool trip they went on to a cool place.

      Reply Link
      • TheRascal March 9, 2018, 1:33 pm

        “You don’t purge your life experiences just because you break up.”

        I totally agree!

        For me, I was on the insecure end of the stick when my husband and I starting dating. My ex had cheated on me and so I was SO WARY of trusting someone new. But with a lot of self-reflection and therapy, I worked on my own insecurities.

        This all leads to the following: when my husband I first started dating — like waaaaaay in the beginning — he had Facebook albums of trips he and his ex had taken. I asked him about it, uncomfortable with the idea that he was “holding onto” these pictures and convinced that he was secretly pining away for his ex. He said to me, “But I had an awesome time on that trip. Why would I want to erase something that happened? We broke up for a lot of reasons but it doesn’t mean that the past just disappears.”

        He also has albums of a bazillion other things on his facebook and literally never deletes a pic. His trip albums had nothing to do with his feelings for his ex and my discomfort was a symptom of the deep insecurities that I needed to work through.

  • Avatar photo

    Skyblossom March 9, 2018, 12:30 pm

    Dating someone who is on a break means you are dating someone who is hoping or expecting to get back together with their ex.

    If they bought tickets before he met you they were both locked into the trip or he has to pay for the trip but not go. I wouldn’t skip the trip for a six month girlfriend. If they bought the tickets after you met him then it is much more of a red flag. I see the trip more as a cautionary tale about planning too far in the future with a boyfriend/girlfriend. At least they didn’t buy a house together, just a trip. Sometimes I think that when people feel a relationship slipping away they try to force it to last by doing things like locking in a trip a year in advance. That way they will have to stay together but those types of tactics don’t work.

    Reply Link
  • dinoceros March 9, 2018, 1:23 pm

    LW1:I’m a little confused. You said they were on a break, but never said they broke up. If they never broke up, then she’s not his ex, she’s his girlfriend (maybe I’m wrong, I know nothing about breaks — I think they’re dumb). It’s risky enough dating someone who recently went through a breakup, but to date someone who is simply on a break is an incredibly bad idea. Clearly there is something there — feelings, drama, whatever — related to why they are on a break, not a breakup. Sounds like he’s trying to keep you on the line in case things don’t work out with his “ex.”

    LW2: When someone says they don’t want to be with you, believe them. Just because you want her to take you back and you want her friends to be right doesn’t give you the right to assume THAT is reality instead of what she actually told you. Please stop hanging out with her friends. It’d be one thing if you’d been together for years and they were equally your friends, but as “cool” as they are, it’s just making it harder for you BOTH to move on.

    LW3: Have you asked him?

    Reply Link
  • anonymousse March 9, 2018, 1:35 pm

    LW1: you should have never started seeing him, a man on a “break.” He was not broken up with her, they were on a break.
    You were the side chick in this scenario, I’m sorry to say. The things he’s saying to soften the blow-he blow that you must have known was coming-are sweet nothings that he knows you need to hear.
    Don’t date men who are still in relationships or hung up on their exes. And block him completely.

    Reply Link
  • brise March 9, 2018, 3:32 pm

    LW1: I would ignore this letter. Don’t answer. You won’t engage in an exchange with a man who is playing both cards at the same time, keeping both options open. Who knows about his ex: maybe he needs to go through this trip to move on and get over her, may be he wants to try again with hers, may be he will remain up in the air. Anyway, you can’t embrace a relationship with a man who can’t make up his mind. If I learnt one lesson about men, it is: don’t be too kind. Be tough. Let him go on this trip, and ignore him. Refuse any relationship with a guy if it is not fully with you. Set the bar higher than this mess.
    LW2: if she calls your mother because she feels guilty to leave you, just give up. And forget about this “reassurance” request. You diminish yourself in a woman’s eyes if you try to control her exes and guy friends. Disengage on the contrary, don’t act jealous. But this ship has sunk anyway, it is over.
    LW3: it is everybody’s right to keep memories about one’s past.

    Reply Link
  • baccalieu March 11, 2018, 4:53 pm

    LW3: What does it mean? It probably means that you’ve been through every drawer and cabinet in his home, even though you’ve been together such a short time that you still call yourself “the new girlfriend”. Either that or you’ve grilled him extensively on what keepsakes he has from his marriage. Either way it doesn’t seem like he is the one in the relationship that the other party needs to worry about.

    Reply Link

Leave a Comment