How Do I Know When It’s Time to Move On From A Relationship? — RUBY ANSWERS

Dear Ruby,

I feel like I am so lost. I recently started seeing a guy, who I really enjoy spending time with and I don’t want to “date” anyone else. But it’s complicated. He plans to move out of state in a couple months and we have yet to really define our relationship. I’m terrified of losing him, but at the same time I don’t know if I should keep seeing him. He has a lot personal issues he needs to work on and everyone tells me he’s not worth my time. But the thing is I don’t mind his issues and who knows maybe I can help him figure them out. I don’t truly know what he wants but I want to spend as much time with him as possible before he leaves.

How do I determine when it’s time to move on?


Dear How,

You: “I feel like I am so lost.”

Me: I’m so sorry. I can relate very intimately to the feeling of confusion and astray-ness that this relationship has caused you to experience. It sounds like you’ve found yourself at a crippling crossroads, where both paths lead to equally lovely and challenging outcomes. You’re not alone in your plight to navigate the stormy seas of relationship ambiguity.


You: I’m seeing a guy who I enjoy spending time with so much, that I don’t really want to “date” anyone else.

Me: How lovely. Regardless of the impending circumstances to come, it’s special and wonderful you enjoy spending time with this boy. I think, too often, we find ourselves scared to just enjoy life, for fear that the good things will not or cannot last. We’re always so worried about what’s just around the river bend, that we fail to run the hidden pine trails of the forest. My darling, when things are tumultuous and unsteady, it’s so very easy to get lost in the heaviness of life’s choices. 

But truthfully, there is so much goodness in our lives exactly as they are right now. And I say this because, while the rest of your question feels heavy and stormy to me, this one little sentence feels bright, joyful, and filled with light. You enjoy spending time with this boy. That’s a wonderful bright spot. Don’t overlook it. I might even encourage you to list the other bright spots in your life–right now. Make a list. I’ll share with you some of the things on mine:

  1. I live a few minutes from the most beautiful mountains, I believe, in the world.
  2. Chocolate milk (preferably Fairlife, but I’m not picky).
  3. I’m reading a really good book.
  4. I have so many hilarious friends.
  5. There are many people I love.
  6. The Office.
  7. My room is clean. I love being in my room when it’s clean.
  8. I love the shoes I’m wearing today.
  9. I can’t wait for lunch.
  10. The tree outside my house is blossoming.

What’s on your list? We’ll return to it later.


You: “But it’s complicated.”

Me: Of course it is. I don’t mean to be invalidating, but: of course it is.


You: My relationship with a boy I like spending time with is 1) undefined, and 2) plagued with the rather difficult reality that he’s moving away.

Me: I’m not trying to unnecessarily simplify a complicated situation, but that’s exactly what I’m trying to do. Why is your relationship undefined? Is it because you haven’t yet discussed your feelings for each other? Is it because you haven’t yet shared with this boy that you enjoy spending time with him and don’t want to “date” anyone else? I’d guess that’s what you mean by “undefined.”

I have a dear friend who has been seeing a boy for a few weeks. And by “seeing,” I mean dating. I mean, they have been technically seeing each other, but yeah. Okay, you get the point. Also, they met on Mutual. (Just a quick shoutout in an attempt to help relieve us of the pertinent stigma that exists around online dating. Nbd.) ANYWAY. She’s been kind of torn up inside, because she’s really starting to maybe-kinda-but really fall for this guy. I mean, she’s kind of like you–really enjoys spending time with him, doesn’t want to “date” anyone else, etc. And while it’s been clear to her that he’s also interested, he hasn’t yet made any moves to initiate the tender, relationship-y things that we all appreciate experiencing. There’s been no hand-holding-in-public, or soft-touching-of-her-face, or tender-kisses-goodnight type stuff. And it’s been driving her a little bit crazy. She’s a very emotionally intelligent person who has no qualms in discussing difficult “relationship things,” but she’s been struggling with navigating the “right time” to bring it all up–to define it all.

I used to think there wasn’t a “right time,” but I also used to think Donald Trump would never win a presidential election (nobody panic–that’s not a political statement; it’s simply a statement of fact). But there is a right time to carve out some definitions, and the right time is: when you feel like you need it. If you’re unable to rationally work through the insecurities of relationship ambiguity that naturally collect like tumbleweeds on the side of a desert highway, and find yourself wanting some definition, then you should ask for some definition. The biggest mistake we make in relationships is not advocating for the things we need or want. There’s simply nothing wrong with having a conversation about where you stand. I’m not honestly sure why our culture seems to feel any differently. Sometimes we feel like we’re “crazy” or “needy” for wanting to feel secure and safe in our platonic and romantic relationships. I don’t get it. Getting our needs met is the only way we’ll ever learn to be in healthy, successful relationships. Getting our needs met means our relationship road trip is using a GPS as a guide to destination Secure Love National Monument, rather than a manipulation map that’s guiding you to Awful Miseryville, population: you. Getting your needs met by talking and addressing them is how you avoid weird game-playing and the inevitable heartache that the weird game-playing yields.

You’re clearly not content with the obscurity in your relationship, so you need to un-obscurify it. I’m sorry to say, but this isn’t easy. It isn’t comfortable. It isn’t fun. But if your relationship is going to have any shot at success, you simply must do it. Tell this boy who you enjoy spending time with that you enjoy spending time with him. Tell him you don’t want to date anyone else. Be honest. Ask him how he feels about you, and if he happens to feel the same way (and I imagine there’s a good chance that he does), then move forward from there. If he doesn’t, your decision has already been made for you! It isn’t easy, my dear, but it is simple.


You: “I’m terrified of losing him but at the same time I don’t know if I should keep seeing him.”

Me: This is the part that isn’t easy or simple. Because, after moving through all the previous steps, you’re still probably going to find yourself sitting on the I Don’t Know rock right in the middle of the What Do I Do river. I’m sorry you’re stranded there. The simple reality is, hundreds of thousands of millions of us find ourselves stuck on that rock, in that river all the time. One riverbank represents moving forward with the relationship, and the other represents ending it. It would be great if one side of the river was lush, green, and breathtakingly beautiful, while the other side was just covered in garbage, or dog poop, or green beans (I don’t really like green beans). But more often than not, both riverbanks look pretty similar. They’re beautiful and green, with like, maybe one pile of dog poop (and also, there’s a can of green beans that you have to eat before you can keep walking).

So, first, (and only you can truly know), do both sides of the riverbank look about the same? If they don’t, then you have your answer. It might not be the answer you want, but it’s the correct one nonetheless. If both banks do look just about the same, then, woof (see; I knew there was a dog around). All I can say is, this isn’t going to be easy. It isn’t going to be simple.


You: “He has a lot personal issues,

Me: “Don’t,


You: he needs to work on.”

Me: we all.”


You: “Everyone tells me he’s not worth my time.”

Me: Everyone tells you that? Who constitutes everyone? Your family? Your close friends? Co-workers? Yourself? Have these people shared why they believe he’s not worth your time? Have you asked them? Do they have what seem to be legitimate reasons, not just reasons based in lack of awareness or understanding? Do you know for certain everyone feels this way, or are your own notions based in unrevealed assumptions? Once again, I would encourage you to engage in some foundational conversations with everyone and learn, perhaps, why they feel the ways they do.

Also, be grateful for everyone. I once dated a boy for almost a year; I knew it wasn’t going to work just a few months into our courtship, but because I loved him, I justified it for reasons that seems so foggy and unfounded when I now recall them. I did a very good job of fooling the everyone in my life, and most of my friends and family were confused and shocked when our relationship ended and I revealed how destructive and toxic it had truly been. But in that relationship, everyone was me. I knew in the depths of my soul it wasn’t right, but I stayed perched on that rock in that river, refusing to admit it.

My point is, whoever everyone is, if they have clearly and reasonably articulated reasons for believing what they do, and if those reasons feel right, if they sound right—they’re probably right.


You: “But the thing is, I don’t mind his issues.”

Me: “Issues.” We all have ‘em. I don’t know what this boy’s are, but you seem to. So, you get to make a choice about them. Your letter seems to imply whatever they are, they’re not dealbreakers for you right now. I’d invite you to ponder and reflect on whether they could ever be dealbreakers to you. I’d also invite you to honestly answer this question: Am I fine with these issues because I really like this person, or am I fine with them because I’m truly fine with them? I understand that our feelings for someone will shade everything with lenses of rose and gold; that’s the really cool thing about love–we love people despite and in spite of their “issues.” But seeing as you’re not committed to this person for time and all eternity, the opposite in fact, you have some room to make decisions. As John Mayer would say, “Give your heart, then change your mind; you’re allowed to do it.”


You: “Maybe I can help him figure them out.”

Me: Maybe. But maybe not. And here’s the thing I want to make expressly and explicitly clear: you can’t change anyone but yourself. You just can’t. Read it again. Read it over and over and over. Read it now, read it tomorrow, read it in 10 years, because that’s how many times we all need this reminder.

I think we all know it to be true. We get, in theory, that we can’t change people. And yet, so many of us are engaged in unhappy relationships–platonic, familial, and romantic alike–because of unmet expectations. “I wish my boyfriend  just spoke his mind more,” or “If only my mom was nicer to my friends, I could have a better relationship with her.” The list goes on and on and on. And sure, our influences or presences or interactions with people can inspire change. But true change must come from within. Always. No one makes permanent, sustainable change simply because someone else wants them to, you and me and this boy included. That’s just not how it works.

So, if you decide you want to date this boy, you’ve done just that: decided to date this boy. This boy in all his glory and joy, lightness and darkness, definition and oblivion and, yes, his issues, whatever they may be. Don’t EVER enter a relationship with any semblance of thought about how once a person changes, things will be perfect, good, happy–whatever. You get to pick the person you date/befriend/marry, and in doing so, you are both consciously and unconsciously agreeing to accept them for who they are. Anything less than that is a disservice to them, and a disservice to you. Everyone–woman, man, child, grandmother, drug addict, hobo and his dog, teenager, politician, teacher, student, realtor, mother, prisoner, etc.–deserves to be loved for exactly who they are without condition, without yearning, period.

Maybe you can “help him figure them out.” But if that’s your expectation, I can assure you your relationship will not be long-lasting, and if it is, it will not be happy. So many of us enter into relationships with other people hoping they will save us from the hurt and pain and trial we each have to endure. But no one can save you from those things. Not even Jesus Christ, initially. He performed an eternal atonement precisely so that you could experience those things. It’s part of our life on Earth. It’s just exactly what we signed up for. And the best people I know in this life are the ones who don’t need other people to save them, because they’ve figured out how to save themselves.


You: “I don’t truly know what he wants but I want to spend as much time with him as possible before he leaves.”

Me: It sounds like there’s a lot you don’t know about what you want, but, you do seem to know this, so, I’ll make this final point:

None of us know exactly what we’re doing. Most of us don’t even know anything close to exactly. Life is a place where we’ve been given the opportunity to make choices, make mistakes, and then learn from them both. I don’t know what you’ll decide to do, my dear. But the point of all of this is, you do get to decide. And that’s pretty cool.

If you read these words and find that they’ve helped you decide which side of the riverbank you’d like to end up on, that’s really wonderful. If you read these words and find that you feel more paralyzed on that rock than ever before, know that it’s okay. And also know this: very rarely do we step off the rock and are flushed down the river and over the edge of no return, but so often, we’re afraid that that’s exactly what’s going to happen.  If you make a choice and it turns out to be the wrong one, there are a million things, people, places that will help you get back on your feet and onto the other side of the river. The only thing that’s the end of the world is, well, the actual end of the world. I’d invite you to return to the list you made earlier, and realize that no matter what happens, there are so many good things in your life.

Eternity isn’t a straight line. It’s a point A and a point B and with lots of windy, scribbly, noodle-y lines in between. It’s lots of rocks and lots of riverbanks.


You: “How do I determine when it’s time to move on?”

Me: The largest river in the world is the Amazon. It’s NINE miles wide at some points. I sure hope I never get stuck on a rock in the middle of it, or have to pick which side of it to cross over toward. I hope you don’t either. But if you do, just know that there are well over one thousand smaller rivers that feed right back into it, so, if you follow any one of them, you’ll end up at the bottom, safe and sound, just exactly where you belong.




Author profile

Are you searching for an answer to a particularly difficult, embarrassing, or confusing question? Perhaps you're unsure about a tumultuous relationship in your life or feel overwhelmed by concerns you have about God, friends, family, or even yourself. Maybe you're feeling hopelessly lost, or, gratefully found. Ruby wants to hear from you! Submit your anonymous questions and letters in the 'Ask Ruby' box, located on the right side of the page, and read previous Q&As by clicking on the Ruby Answers tab.

You Might Also Like