My Boyfriend Doesn't Care About His Extreme Debt. Red Flag?

Q: For two years, I’ve been in a relationship with a kind, compassionate, understanding, selfless, and loyal man who always puts me first. However, I have a lot of concerns. He has very little savings and severe financial debt (and he’ll inherit more once his parents pass). He is a big procrastinator and we don’t have much in common. He’s an early bird, outdoorsy, athletic man and I’m a homebody night owl. I’ve spoken to him about his procrastination habits and lack of savings, but with very, very little progress made over a significant time period. We also have a large age gap — don’t worry, I’m 25 and he’s 40.

Since I am still young, I’ve been finding myself wondering what else could be out there and thinking about going on solo adventures. I find myself not getting as excited to hang out with him, as I feel very bored no matter what. I haven’t wanted to engage in intimacy as much.

I love him dearly and will always be grateful to this man who was the first ever to treat me with love and respect. I would feel absolutely terrible leaving him. I don’t want to hurt him or make a huge mistake. But I also don’t want to have regrets. What do I do?!

A: Because kindness feels so hard to find in today’s dating world, it feels so hard to part with. At least, that’s my suspicion based on how many letters I get that basically amount to, “This dude and I don’t work, but he’s nice. What do I do?”

The answer pretty much always is: Leave! Hit da bricks!

I don’t necessarily think you’ll be miserable if you stay. I just think that — after about seven months of sticky sadness — you’ll be a whole lot more fulfilled by moving on. What is your one single life on this earth for if not being happy? You don’t get another 20s. There isn’t a genie who shows up on your 47th birthday and asks if you want a redo. This is it.

His Finances: Red Flag?

To me, the money is a nonissue because — theoretically, at least — it can be solved. In most cases, people don’t inherit their parents’ debt. I am not an expert, obviously, but he should speak to his family about this. He could also get serious about saving, or work with a financial advisor to chip away at what he owes. Of course, he simply isn’t doing any of this.

I want to be clear: Financial issues aren’t a red flag on their own. Refusing to address them is.

Anyway, all of this is peanuts compared to the sentence, “I feel very bored no matter what.” I mean, come on!

Here’s The Bigger Problem

Good, steady love is undeniably mundane, like warm socks and a nice chair and bowl of oatmeal. And then seeing a really cool bird outside your window. It’s not confetti and glitter and roller coasters. (And it’s fine if you want those things — your 20s are a wonderful time for that.)

But the person you love isn’t meant to bore you. Certainly not two years in! Not for sustained periods of time! Maybe for a month or two when your baby is 4 months old and has sleep regression and colic. But not now!

After the initial “spark” (anxiety disguised as chemistry) burns off in a relationship and you’re left with the reality of a person, things get a little less thrilling. But you two don’t seem to have the foundation for a satisfying relationship. You have massive incompatibilities and valid complaints about him.

Imagine that someone gifts you a brand new limo. New car smell! No check engine light! The AC works! Free car! At first, it’s exciting, but eventually you realize you’re spending a fortune on gas and can’t actually park anywhere. It’s simply not the right car for you. And that’s OK.

I know you said not to worry, but the age gap does stand out, considering that you’re in your mid-20s. This guy has 15 more years of life experience. Fifteen years ago, you didn’t know long division, and yet, you’re the one trying to communicate practical concerns. Think about that.

Of course, there are ways to enjoy your current phase of life while dating an older man. You can go on a solo trip to Machu Picchu or direct a short film or find other 25-year-olds to go to bad dive bars with. In fact, if you do stay with this guy, I recommend that very strongly. (Or whatever your personal idea of a good time is.)

A good relationship, however, is not something you fantasize about escaping from.

My Two Cents

I know you don’t want to hurt him, but leaving will do just that. I wish I could tell you otherwise, but that is the cost of loving people. That’s the crappy agreement we enter into when we date someone — that at least one person will get hurt, whether it ends in a breakup, divorce, or death. But until we figure out a better way, or until an asteroid kills us all simultaneously, that’s what we’ve got. Plus, sticking it out is not a cheat code for preventing his pain. You do not want to damn him to a life with someone whose heart isn’t it.

As for if you’ll regret it? If the relationship isn’t working for you now, that’s enough reason to end things. Don’t try to guess what Future You might want — if Current You isn’t happy, that’s all you need to know.

Regret does not usually look like, “I did the scary thing that my heart wanted, but I wish I’d played it safe.” I certainly haven’t ever had a conversation like that with an elderly loved one. Have you?

I think you know what you need to do, and I think you’re sad about it, which is fair. It is unbelievably heartbreaking to not be right for a wonderful person. But look at your own words. You write about him as if it’s a foregone conclusion that he’ll be part of your past: “I … will always be grateful to this man who was the first ever to treat me with any kind of love and respect.”

Trust that you will make the right decision. On your 47th birthday, you’ll look back, smile, and thank yourself for being brave enough to take the leap.

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