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Dear How to Do It,

“Jack,” a 36-year-old man, and I, a 29-year-old woman, have been dating for about six months and are very deeply in love. We’re both weird, introverted nerds who never dreamed we’d find someone we’re so into who’s so into us. He is actually my first ever serious relationship, and I’m his second. Jack is still close friends with his ex, “Robin,” whom he dated in college.

Let me be very clear, I am not jealous or afraid Jack will cheat with Robin. Not just because I trust him, but because Robin is not really able to have sex. Robin developed multiple chronic conditions in her mid-20s, which have left her severely disabled. She has very little mobility in any part of her body without terrible pain. She uses a walker/wheelchair and often needs help doing basic tasks. She rarely leaves her (wealthy) parents’ house. The exceptions are her vacations with Jack, which are typically once or twice a year and consist of cruises and trips to various Disney parks. Robin pays both of their ways in return for Jack caring for and assisting her throughout.

If we were also independently wealthy and didn’t have to take vacation days from work, I would be OK with this. But their next trip together is coming up, and I’m thinking about how I’m going to feel in the future if Jack continues to use up most or all of his vacation time going on trips with Robin, instead of me. I don’t want to push to go with them, for several reasons:

1. Robin is not someone I enjoy interacting with, and I’m sure she feels the same about me. She is very blunt and critical, I’m very sensitive, and we have zero common interests.

2. I don’t like cruises or theme parks, and the kind of vacations I would like, and Jack admits he would too—remote island getaways or walking through old European cities—would not be possible for Robin.

3. Having to accommodate Robin’s pace and schedule, and having so much of Jack's time taken up with her, would make the trip less fun for me, regardless of the destination.

4. I can’t afford to pay my way on so many lavish trips, I wouldn’t want Robin to, and I’d prefer Jack save his money for other things.

However, I feel horrible about wanting to ask him to dial these occasions back, because I know they are the highlight of Robin’s otherwise very depressing life. How and when can I begin to talk to Jack about this without sounding jealous, possessive, or like I’m planning our whole life together too early in our relationship?

—Only Jealous of His Vacation Days

Rich Juzwiak: I think that the letter writer has every right to voice concern or complaints about her boyfriend’s time being taken up so much, very specifically by somebody else. But at the same time, if Jack is 36, we’re talking about a potentially up to 15-year-long tradition versus the six-month relationship he has with the writer. It’s a tough thing, but Jack is showing who he is this early in the relationship. He’s showing that if you want to be with him, this is one of the stipulations. He’s sometimes going to travel with Robin. I think it’s going to be really, really hard to make an impact or to not feel like you’re infringing at this juncture by speaking up.

Jessica Stoya: I think it’s interesting that the first mention of jealousy is through this classic cinematic interpretation of the physical and lust. It’s followed by all of these physical reasons that Robin cannot act upon what is commonly considered sex. And then there’s the “I don’t want to sound jealous.” Many years ago, a woman who went by Her Dirty Little Heart on Tumblr wrote something for Feeld. It appears to have gotten lost, but it was about jealousy and how the feeling that we call jealousy can often point us to something we are missing. Does it become right to try to take what we want from someone else? No, but that emotion can be very important information that you’re missing something. In this case, a partner who makes time to be on vacation with you.

Rich: Yeah. It’s a real pickle because this is his lifestyle. And at the same time, our writer, I think, has very reasonable expectations of ways to spend time with her boyfriend. It’s her first boyfriend. This is a big deal for her. She never thought she’d have this. Now she has it, and she can’t go on vacation. Going on vacation isn’t necessary with a partner, but it’s pretty fundamental. That’s something couples do together, and this is making it impossible.

But, at the same time, he’s coming with a sign attached to him saying, “Unless things change, this is impossible.” So what do you do? I don’t think that there’s anything wrong with talking about this, but trying to change the situation, trying to really exert influence in there, is going to be tough. On top of it, he’s doing something kind. He’s taking somebody on vacation who our writer assumes has a miserable life. I don’t know if that’s actually true, but certainly these trips are a highlight. If you like going on cruises and going to Disney, when you go once or twice a year, that is a highlight. I can tell you that as somebody who loves Disney.

Jessica: I have so many things that I am not on board with assuming, including that Robin actually likes cruises and Disney, because, for instance, I dated someone many years ago who had a parent who could not move around the world without their wheelchair. Visiting New York City was a nightmare because it became a question of, “We’re going to this place. Where is the nearest subway station that actually has a functional elevator? Because if they have an elevator, great. Is it currently working right now today?” Or, “We’re going to take a taxi, but is it going to be a taxi that can accommodate the wheelchair? Also, are we going to be able to get one of those for the way back?” Just logistics hell.

I can absolutely see a world where Robin’s like, “I don’t even like cruises or Disney parks, but I don’t get to go to Europe because it’s not very accessible.” Truly, most of Europe is not accessible. But whether Robin actually enjoys the cruises and Disney parks is a question for me. Whether her life is entirely miserable outside of these trips with Jack is also a question because it’s really easy to overly empathize in a tragic fantasy way with various marginalized people.

Rich: At a certain point, it becomes projection.

Jessica: Yes. So one thing that I think would be really useful for the writer for herself, and especially to keep in mind as she’s broaching any kind of conversations with Jack, is that she doesn’t actually know a lot of things that might feel really reasonable and empathetic to fill in.

Rich: For sure. But what she does know is that her boyfriend is willingly doing this. This is part of who he is, and part of the early stages of a relationship is determining compatibility. You learn more about people the more time you spend with them, and that gives you the tools to say, yes, this will work or this will not work.

It could come down to whether you’re going to accept this or not be in the relationship, and then what’s the trade-off? It doesn’t seem to me, given the gushing first paragraph that we got, that it’s going to be worth abandoning this relationship because of this. Maybe this is a situation where you say, “Well, as of now, given our time off allotment, we don’t go on vacation together. Maybe we work toward getting more vacation time.” But this might be a concession to make, and it might be one worth making because again, your boyfriend is, from what we can tell, given the description, doing a nice thing for somebody. He’s helping his disabled friend, with whom he has a past, and who he clearly cares about, have an enjoyable time. She needs assistance according to the letter, and he’s providing that.

If he’s willingly going to Disney—and I am willing to believe that they both love it, just because I love it, so this is my Disney adult fantasy—but it’s at least plausible that he’s enjoying some part of this trip. It also sounds like a fair amount of work. It’s really hard to tell somebody, “Stop doing that nice thing for somebody.” Now you’re going to get his heart involved in it and make him torn.

So I would say tread lightly when broaching this conversation. You could ask, “Do you think we’ll ever go on vacation together? Just given the logistics here, how do you see that actually happening?” Maybe he has a hypothesis or a plan in his head. Maybe he’ll say, “Oh yeah, we’re getting more serious. This Robin thing isn’t sustainable. Instead of going on vacation with her twice in one year, I’ll go on one with her and one with you.” Just get him thinking about it, but be prepared to accept the answer you don’t want to hear or to have to make hard decisions about this relationship that you hold so dear.

Jessica: First relationships, especially when people are doing that in their late 20s, can feel like this is the only person in the world that you’re ever going to feel this way about. There can be a lot of internal pressure. So I’m a little worried that our letter writer might be trying to game out a future while missing a lot of variables. You don’t know what’s going on with Robin. You don’t know what’s going on between Robin and Jack. You don’t know where Jack is going to put his priorities.

She might also be able to think about Robin a little differently, for example, “Oh, Robin’s very blunt and critical, partially because that’s how she’s wired and partially because living in a world that is structurally not built for you makes people a little more sharp and short.” So our writer might be able to say, “You know what? I’m just going to put everything through a Robin has good reason to be sharp filter.” This might be able to help her grow beyond her sensitivity and meet in the middle. Also, you don’t have zero common interests. You both care about and respect Jack.

Rich: Great point.

Jessica: So there’s a world and remote island getaway, and most old European cities, that are very much not set up for wheelchairs, but there is a whole internet full of people who have gone through Europe in wheelchairs. I was in Switzerland, and one of the people in the group was in a wheelchair. He got around perfectly fine. He made it work. He knew what he needed. So there’s also a world where Robin’s like, “Yeah, actually really tired of Disney, and if both of you are willing to help me with the accommodations that I know I need and any surprise accommodations, we can all go together.” All that to say, there are lots of ways to make this work if everyone involved wants to. So, try not to dig into the position that this absolutely will not work at all without first discussing it with anyone.

Rich: Exactly. I think the bigger picture, to circle back to your point about jealousy, is that Robin is an important person in this person’s life. It’s just not wise to come in and start asking that they make other decisions—not after six months and not with something that isn’t immediately problematic and toxic. So there is a certain amount of respecting your partner’s life that he’s already built that I think needs to be front and center whenever you bring this up. And it’s OK to talk about this stuff.

Your partner is so into you and obviously an extremely compassionate person, so I can’t imagine it going poorly. I think that you’ll be able to make some headway, or at least gain clarity, reassurance, or a nice prediction for the future about how things may shake out. But just don’t expect to delete Robin from the picture with one conversation. I don’t think that you should, in fact, try to do that at all.

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