#1312: Did I make the wrong decision? And–why can’t I listen to everyone telling me I made the right decision?

Hi Captain Awkward,

I stumbled upon your site due to Ask A Manager. Your archives are very helpful, but I’m hoping you can talk to me about my situation. I’m really not sure if I’m dealing with a Darth Vader relationship.

I am so, so sorry for how long this is.

I’m 28 (she/her) and my now ex boyfriend (he/him) is 41. I’ll call him Han.

Early 2019 I went through an incredibly hard divorce, and my therapist helped me figure out what was missing from my marriage. Han and I became quick, close friends. Han and I were part of a hobby group that hung out a lot, and that’s what got me through my divorce.

I started dating and fooling around with Han before the divorce was official. We have so much in common. You’ve probably heard all the cliches, but with Han, I felt like I was on fire in a way that I never felt in my marriage. We love the same things, have the same hobbies, and when times are good, they are really really good. Politics, religion, absolutely-no-kids, we agree on it all. He inspires me in ways that only poets can write about.

And I started finding out about his financial issues. You see, he quit his job years ago (in his 30s, I think) to get a second degree that didn’t pan out. And then his mom passed away, and he had to deplete his retirement and savings. And then he inherited her house, but sold it and just lived off the inheritance. Thought he could go back and get that second degree, didn’t. All this time he was doing Lyft to make ends meet, and hasn’t filed a tax return in years.

I understood some of his issues while we first were together, but I was so high on post-divorce love and bedroom stuff I hadn’t gotten with my ex-husband. I didn’t want to break up with my intellectual and romantic match because of money. That’s silly, right?

But ride-sharing died during COVID, and Han decided to go to another college program. Spent the rest of his mom’s inheritance and then some on it. Couldn’t afford rent. Didn’t get unemployment for whatever reason. Tried delivering food until his car died. He didn’t ask for it, but I loaned him money, and my car. I suggested he take a break from college to save money. I sent him remote job applications. I told him to ask his friends for help. He said I was nagging. I’ve spent countless nights crying to my friends (who said dump him) and to Reddit advice forums (that said be patient, with a smattering of dump him), while simultaneously hiding all these problems from my parents. Then his dad died. Then his dog died. COVID brought such a perfect storm onto his life, and since he helped me through my divorce, I wanted to be strong for him and show him I was worth committing to.

But…when there are issues I want to talk about, he doesn’t communicate well. I remember once he told me he loved me, but didn’t think he could ever fall “in love” again. He got defensive about finances. We talked about moving in together for a while (we spent all our time together due to COVID anyway). October move-in became early November. Then he said he’d move a bunch of his stuff over Thanksgiving. He didn’t. He said he was focusing on school. Gave other small excuses. Talks of future commitments like marriage and a house were, “I’m thinking about it,” or, “I’m getting used to the idea.” But maybe I should’ve just accepted he could never afford a future with me.

He finally got evicted in December, and I paid for movers to move him to my place. I finally told my parents everything. They drove thousands of miles to visit me for Christmas, and my dad insisted Han stay with a friend because he “didn’t want to see the man that emotionally abused my daughter.” Was this really emotional abuse?

Over Christmas, my parents convinced me to move home all the way across the country. While at his friend’s house, he found a temp job, and when he came home told me, “If we can get through this, we can get through anything.” I thought, if Han could find a job and settle his finances, he could come with me cross-country, right?

But I couldn’t stop crying. Each day since Christmas, I’ve cried myself to sleep. Han felt conflicted about moving. I couldn’t look past all I had helped him through.

Last week, after crying to my mom, my dad grabbed the phone and said, “You can break up with him, you know.” I asked my friends, and they agreed I needed to dump the guy. So I did. I don’t want to cry each day anymore.

And yet, I miss him. I feel like I’m making a mistake and losing the love of my life. If I could’ve just hung on and helped him through COVID, maybe we could’ve really been forever.

I’m getting on my parents’ and friends’ nerves because I’ve spent the last week crying to them that I want to take Han back. I finally saw my therapist again yesterday, and he thinks leaving Han and moving across the country to live with my parents sounds great for my own healing.

But love should be able to conquer all right? Financial issues, COVID, disapproving parents? What do I do? Do I text Han and ask him to take me back? And if not, how the hell do I listen to everyone begging me to leave him and move home?


Will you try something for me? Imagine that “Han” is out of the picture for the time being because he got a once-in-a-lifetime chance to study space rocks on the International Space Station, all expenses paid. In this story, Han actually broke up with you before he got into the spaceship for his new gig because he didn’t want you waiting around for him, and it was very sad, but Han is fine. Han is doing what Han needs to do for Han. He’ll be back on Earth in two years, maybe three, and nobody made any promises. I want to temporarily remove him from your decision matrix and your field of vision, and look at what’s left.

Please also imagine that COVID-19 is over and you can go anywhere, live anywhere, do anything you want. With those parameters:

Where do you need to be?

Where do you want to be?

Is it with your family? Is it in the city that you’d be leaving, the home that you have now? Is it somewhere in between, or somewhere else entirely? 

If an envelope were to turn up in your mailbox with an invitation to your dream career, your dream house, your dream life, the way it did for our version of Dream-Han, what’s written in the card? What are all the daydreams you have that don’t star Han in them?

I ask because I see these three anchors surrounding you:

One is your life with your ex, and all the ways that life was shaped by your ex, by making decisions as a “we.” You’ve broken free of that one, but you can still feel its weight behind you.

One is your parents. “Leave him, come back to us!” 

One is Han, and Han’s series of disasters, and also the way he smiles and how good he smells and makes you feel, and the way he’ll be desperate for your help one minute but call it ‘nagging’ the next, the way he avoids addressing problems until they multiply, the way love can feel more exciting when it’s a maybe.

Imagine you are a little boat. The three anchors make three points on a triangle, and you’re searching for your safe harbor within its outline. I don’t know what it looks like from inside the triangle except from what you’ve told me, but from out here I can see the whole damn ocean. So I can’t help wondering, if Han’s anchor went floating up, up, and away all of a sudden, where would you need to go?

Looking more closely at some of your anchors, I’m noticing more patterns.

Your parents want to rescue you. You don’t have to date only men that your parents approve of, and you don’t have to move back in with them in order to break up with him. They are trying to save you from pain, and prevent you from making a mistake, and they might be completely right about Han and about what you should do about him, but the reason it doesn’t feel better right now is that you miss a person who made you feel good and also because it doesn’t feel like your decision yet. I know that cry well, the one that says well, dammit, if I’m going to make a mistake, let me at least make my own mistakes and nobody else’s. Additionally, your parents might be right about Han in end, but they might be wrong that the right place for you is where they can keep a close eye on you. You’re chafing at their advice the way Han chafed at your helpful employment listings, and that’s not surprising, almost nobody is like “thank you for being so right about me” even when it’s true.

On some level, you credit Han from rescuing you from your failed marriage and you want to rescue Han right back. You don’t have to un-fuck Han’s money situation or manage the career of a 41-year-old man from the ripe old age of 28. You don’t owe him that, and you especially don’t owe it if he doesn’t want rescuing. The gift, or loan, or whatever it was that got him through the falling dominoes of grief and disaster until he could get that temp job can be a beautiful thing you did, like the way he got you through a hard time, and nobody has to marry anybody for it to still be a kindness. You didn’t get him into this mess and you did your best to help him. You’re a good egg, I think, and you tried your best with all of it.

I suspect that Han does not want to marry you, deep down. He definitely doesn’t want to marry you now, like this, because he feels like he has to, because he feels like he owes it to you, because he feels like there’s nothing else left for him to do. He does not want to move away from everyone else he knows to be dependent on you, and to grind away under the gimlet eyes and gritted teeth of in-laws who hate his guts and don’t think he’ll ever be good enough for their daughter. 

Even if your parents didn’t hate him, truly, I suspect Han is good at committing to exactly two things: 1) owning a dog, RIP to a Good Buddy 2) keeping his options wiiiiiiiide open.

If you need a few more “breaking up was a good decision” data points for your pro/con list:

Don’t marry a man who calls it “nagging” when there’s shit that needs doing and a woman reminds him about it. Struggling financially doesn’t mean a person has to accept all offers of help with a cheerful smile, but if Han didn’t want your help, he could have set a boundary: “I know you want to help, but don’t send me job listings please, it makes me more stressed out.” It’s not his fault the economy tanked but it’s not your fault, either! 

I don’t know how to answer the question about abuse. Your dad has heard all the stories, and I haven’t. I’m not getting the sense that Han is a con artist or a leech, if he were, he’d have been wanting to move in with you as soon as possible instead of dragging his feet until he ran out of options. The read I’m getting is less about anger or control and more about shame. This is a person who hates himself for needing help. Shame can be dangerous, and if you and Han had stayed closely involved, I suspect that the more powerless Han felt in other aspects of his life, the more he might try to reclaim a sense of control at your expense, responding to the things you do to make his life easier with prickly, noncommittal reminders that Han doesn’t do anything Han doesn’t want to do until Han is good and ready. Somebody doesn’t have to be abusive to be incapable of making you happy, and love does not conquer all. 

Don’t marry anybody who has you making “pro” and “con” lists and reeling from asking all and sundry for advice about whether you should be with him at all.  And don’t marry someone who makes you cry all the time! 

I truly, truly, truly don’t think that “financially stable, maximally useful to capitalism” and “good person/good partner” are synonyms, credit scores are made-up numbers that have no moral value. Shit happens. You know what didn’t work out for me financially in my 30s? ACADEMIA, where the Venn Diagram of “You are great at this!” and “Here is a living wage!” are two entirely separate circles that do not touch. There was a month in 2011 when I moved out of a bad relationship situation with less than $300 in the bank and had to stitch a whole existence together from the kindness of friends and readers of this website. What gives me pause is not so much Han’s series of sunk costs and truly awful twists of fate as it is the emotional messiness and fog around it. I don’t think you and Han were fully ready or willing to have the kind of clear-eyed “how are we going to money?” conversations that people planning a to share either a household or a lifelong joint venture sanctioned by the state need to have. First, because a man who doesn’t do his taxes might not be able to have that kind of conversation with a piece of overpriced software where you occasionally type in numbers and click little boxes,* never mind a wife, and also because that’s the nature of big decisions made in crisis, whether or not the crisis was unavoidable or was anyone’s fault. High stakes and heightened emotions mean that conversations that should be pretty boring math problems are all about fear, shame, and wishful thinking instead.

(*I currently have to solve a thorny tax glitch from last year that involves my five nemeses: paperwork, re-doing paperwork, the mail, sustained attention to something scary and annoying, and phone calls to the U.S. Government, so honestly, no shame here.  It will get fixed, in my favor, it will just feel like there’s a rock in my shoe the whole time I’m fixing it and also like invisible, disapproving people are mad at me every minute, every day. In Han’s case, to talk about finances with a partner who will be affected by the decisions he makes, he’d have to at least be transparent about what’s happening, and realistic about what he plans to do about it, in a way that also takes your well-being into account, and in a way that attempts some long-term planning instead of lurching from crisis to crisis. Seems like Han’s not quite there, emotionally or functionally, and if he’s foggy about money, legally converting your money into “our money” can seriously, seriously wreck your life.)

If a Future-Han showed up two years from now with a secure housing situation, a competent therapist, even the bare bones of a record-keeping system, and a much stronger sense of what he wants to be when he grows up, he would be a different prospect than the grief-shocked Han-In-Crisis you’ve got now. Not making any big decisions while he is drowning in debt and shame and grief is possibly a kindness he’s doing the both of you.

Don’t plan your life around anybody who isn’t choosing you. “I don’t think I’ll ever fall in love again” and “I’m getting used to the idea” don’t spell “You are the love of my life, let’s fucking do this.” Nor does “If we can get through this, we can get through anything.” HE HAS TO SAY THE WORDS. Do not build a habit of guessing them. Han isn’t the love of your life until or unless he asks you if he can be so and tells you that you are his, at which time you can see how you feel about that. You asked him to follow you home. He didn’t. He knows where to find you if he changes his mind. There were a lot of extenuating circumstances, but he chose to do it this way just as much if not more than you did.

To be clear, I don’t think men are supposed to propose to women, like “surprise, I finally love you enough, thanks for waiting,” but I do think that 41 is old enough to know for yourself if you are the marrying kind and I do think the partner who has been all “oh babe let’s not put any labels or expectations on it” during a relationship is the one who bears responsibility for spelling things out if and when that changes, vs. the other partner “nagging” them about it. Being an emotional cell-phone commercial guy (“Now? Howabout now? Do you love me now?”) is no way to live your life.

The age difference matters, here. Look, we all have our biases. CaptainAwkward.com is never going to be the website where you see the words “You’re 28, he’s 41, cool, yes, definitely sort out all his difficult shit for him over his objections, you can 100% mold him into the man you know he can be, I’m sure it will all work out in the end and you’ll be very happy” minus the deep skepticism and sarcasm. I’ve never smoked anything in my entire life, but I think we could all hear the weary no-filter cigarette drag somewhere in the middle of that sentence. This is not my first time at the Much-Older-Dude-In-Neverending-Crisis-Much-More-Compelling-Than-Anything-In-My-Life-That-Could-Use-Attention rodeo, and you asked me, so me is what you get.

If I’m wrong? Send me a postcard from your honeymoon, I will sincerely be overjoyed on your behalf.

In the meantime, this is probably going to smart for a while, as you get some old-fashioned, shitty, ugly-crying grieving done and regroup for whatever’s next. Han’s going to do the same, and maybe you’ll meet in the middle someday, when it’s more of a romance and less of a rescue operation. If that happens? You won’t need advice or pro and con lists. You won’t need to chase anybody down or force any big decisions. He’ll come to you, and he’ll come correct, in a way that’s easy to say yes to, in a way that makes sense and fits in with the happy life you’ve built in the meantime, or he won’t.

Until that day, you’ve got a whole beautiful life to live, so it’s completely up to you if you’d rather spend the time waiting for him or living for you. I’d strongly encourage you to not text him for at least six months, and to put any and all agreements about money in writing, no exceptions. 

One thought on “#1312: Did I make the wrong decision? And–why can’t I listen to everyone telling me I made the right decision?

Comments are closed.