Hannah Orenstein advises the best time to break up with someone you love in Dating Decoded.

I Love My Boyfriend, But Is It Time To Break Up?

We're so happy together, but I worry I'll miss my chance to meet someone else.

Originally Published: 
Lindsay Hattrick/Elite Daily; Clique Images/Stocksy; Hannah Orenstein

Q: I’ve been with my boyfriend for almost four years. I love him and he is my very best friend. But I know he’s not the guy I should marry. There are small things about his outlook on life, his career choices, and his relationship with his parents that make me hesitant to ever have a family with him. My question is, when is the right time to break up? He’s equally as hesitant about our future (though not for the same reasons) but we are both so happy with each other we have yet to want to split. I’m worried that if we stay together for a few more years I will have missed out on meeting someone that might be my future husband, but at the same time, there’s no one I want to be with right now other than him. What should I do? — Jane

A: Hi Jane! You say that if you stay together for a few more years, you’ll potentially miss out on meeting your future husband. I hate to start by being such a bummer, but the thing is, we’re all missing out on incredible things all the time.

That guy you saw buying pasta at the grocery store last week? It’s totally possible that he shares your dream of visiting every national park, and also loves those TikToks featuring sea otters holding hands, and also gets embarrassingly hyped up about his Duolingo streak. Maybe Pasta Guy has the kind of emotional stability and thoughtfulness that will make you feel safe, and he knows how to work through an argument without getting defensive. Maybe he was even browsing for fusilli, which happens to be your favorite noodle shape, too. You two could have an absurdly happy life together.

But you know what? If you and Pasta Guy never see each other again, you’re not destined for a bleak life of loneliness. You’ll probably bump into someone equally as compatible when you’re renewing your driver’s license at the DMV. We all have infinite possibilities — some that we explore and some we don’t.

My point is that there’s no single “right” time to break up with your boyfriend. You won’t miss out on your perfect person by temporarily staying in this relationship — you’ll just meet a different perfect person later on. Maybe that’s OK. Or maybe it isn’t. It sounds like you’ve already spent some time exploring who you are and what you need from a partner. It’s also worth thinking through a few other questions.

If you stay together for the next few years, what circumstances would eventually prompt you to break up? How would it feel to be in this relationship if you know a breakup will happen down the road? If your current boyfriend isn’t quite the right fit, what kind of person would you want to date instead? Post-breakup, do you think you’d regret your choice to prolong the relationship if you wind up struggling to meet someone else? And not that you can control luck or timing, but when would you ideally want to get married? What do you want the next chapter of your life to look like and feel like? Do you want kids, and if so, does that impact your preferred timeline? (It’s impossible to predict what will happen in the future or how you’ll feel about things, but do your best to guess.)


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I think you should be honest with your boyfriend about your answers to these questions, and you should hear him out, too. You built this relationship together, and together, you can figure out where to go from here. Even if making a conscious decision to part ways is sad, it’d be worse if one of you felt led on or blindsided by a sudden split. If you care deeply about each other, neither of you should want to derail the other’s plans.

Do yourselves the favor of having this discussion at a time when you’re both free to talk, not running out the door or falling asleep. This conversation probably won’t be easy. You might tear up, get tongue-tied, or feel frustrated at times. It probably won’t just be one convo, but several. Once you’ve both openly communicated, though, the path forward might feel clearer.

Maybe you’ll keep dating but won’t move in together or foster a dog like you’ve been talking about. Maybe you’ll agree to stay together and check in with each other regularly to see if your feelings have evolved. Maybe you’ll realize you’re on two separate paths and decide to let go of the relationship. Maybe you’ll start to wonder if you’d be even happier single.

Also, I’m curious about your boyfriend’s take on all of this. You say he’s equally hesitant about the future for a different reason — why? It’s one thing if he’s worried about long-term compatibility, too. But if he’s less emotionally invested in this relationship, or less happy together than you are, that’s a sign to walk away. You deserve someone who lights up around you the same way you light up around them.

I don’t know you or your specific circumstances beyond what you’ve told me, so I don’t know what solution makes the most sense here. But I won’t lie — the fact that you’re asking this question at all makes me wonder if deep down, you already know it’s time to break up and you’re seeking external validation that this decision is right. You might be ready to move on from this relationship but feel like you can’t justify splitting up because you don’t have a “real reason.” But you know what? You don’t need any reason beyond being ready for something new. That’s a perfectly good reason on its own. If you know a breakup will happen eventually, kicking the can down the road doesn’t make it any less painful.

Four years is a long time to be with someone. It’s OK to evolve. It’s normal to feel nervous about stepping into the next chapter of your life. But eventually, you have to take the leap.

— Hannah

Dating, Decoded appears on Elite Daily every other Thursday. Have a question? Submit it here.

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