Knowing When It’s Time to Break Up


There were years between the time I knew it wasn’t right and when I finally walked away. And I learned a lot from the experience. Today, I’m going to talk about knowing when it was time to call it quits and when I finally had the strength to move on.

One of my readers recently asked when I knew it was time to end the relationship I was in for most of my 20s and how I coped with starting over after being with someone for such a long time. Let me preface this post by saying that I am obviously not a dating expert and that not every piece of advice I have to offer or what I went through will apply to everyone. I wanted to share what I went through, learned, and what worked for me.

With each relationship, I’ve pretty much known when it’s been time to call it quits, but even then, it’s not always easy to walk away. Letting go, even when you know it’s not right, can be extremely difficult.

My almost decade-long relationship should have ended about 3 months in, but I didn’t think I was strong enough to break up with him. I can’t remember the exact moment that I knew, but I did. And it wasn’t right.  At the end of the day, if the person you’re dating is treating you in a way you wouldn’t want someone you care about to be treated you need to end it.Any signs of verbal abuse or a lack of emotional support are reasons to say goodbye. That’s not to say your person shouldn’t be there to bring you back to planet earth when you throw a completely insane idea out there, but no matter what, he (or she–let’s just apply that everywhere) should always be kind.

Then there’s how you’re treated when things get difficult. It’s easy to have a great time when things are good, but when life gets hard, do things fall apart? Because if you’re going to commit long-term to this person, you’re going to go through the best and worst times of your life with them. And how someone treats you when things are bad matters just as much (if not more) as how they treat you when things are good.

I finally had my aha moment on July 3rd, 2012 when he called to say he needed space. Keep in mind we were 2,000 miles apart with him in LA and me in Chicago, and hadn’t seen each other since Christmas. I told him to take his space forever and we never spoke again. It was one of those Kate Winslet as Iris Simpkins “square peg round hole gumption moments”.


Going months without seeing him made it easier to walk away. We were over long before it ended, and the gradual break-up process plus independence I gained in Chicago made “coping” that much easier. 24 hours later, I was on a boat on lake Michigan (the only reason I remember the date we stopped speaking) celebrating the country’s freedom along with my own.

I know it’s not always that easy. Trust me.

For some reason, the guys that strung me along until for a month or two were always the hardest to shake. And I made excuses for some real idiots. Like the guy I dated for a few months who I found out had a secret soon to be ex wife, baby, and girlfriend. I didn’t know about any of them and ended it the day I found out. If you’re pining and unhappy most of the time, that’s probably a sign it’s not working. No one is too busy to text. If a guy wants to see you, he’s going to see you. And if you’re being canceled on on a semi-regular basis, there’s probably someone else. Or multiple someones. I never had to wonder if I was going to hear from Conor. Ever. 

I’m not sure what kind of advice I can offer when it comes to moving on since my long-term relationship ended long before it was over, so I suppose I’m not much help there.Ultimately, if you’re not happy and are constantly second-guessing your relationship or waiting for things to change, save yourself some time and move on.

Victoria Smith of SF Girl by Bay said it best when asked what advice she had for her 23-year-old self.

Break up with that idiot. He won’t be worth it.

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  • YES YES YES. My ex and I should have broken up months before we did. The last straw was when I wanted to look at schools out of San Diego and he said he wouldn’t visit or move. EXCUSE ME?! So I booked a trip to Chicago (when I saw you) and New York. We broke up a few days after I bought my ticket. Never looked back.

  • This is great! I clicked on this story after reading your article about dating in your 30s. While I’m only 24, I think your advice is true for people of all ages. I wish I wouldn’t have dated that guy my sophomore year of college and would have spent more time with my friends. I wish I wouldn’t have been pining over that guy that never saw me as more than a friend my senior year of college. Most recently, I had to end things with a guy after about 8 months of “dating” when he told me real, committed relationships weren’t for people our age, only people who are looking to get married (what?!?). I immediately realized how delusional I had been, always making excuses for him when he decided to cancel last minute or just blow me off completely and blaming it on myself. This newer guy I’ve been dating now for about 6 months is like being in a completely different world – I never have to worry about whether I’ll hear from him or not and he’s interested in spending time with me and my friends. While I know I still am young and have a lot to learn about relationships, having those shitty relationships really made me a stronger person and helped me learn who I wanted to be as a young adult.


    1. Hi Taylor! First of all, we ALL have a lot to learn. And the fact that you’re young means that you are ahead of the game! You are already so far ahead of where I was 24 which was TEN years ago. Your new guy sounds like a good one! Wishing you two the best 🙂

  • Love this post Danielle. I went through something similar as well. Dated the guy since I was 15, marry him when I was 25, and divorced him when I was 28. Moved to Chicago (at 26) from Venezuela and even though we tried to work things out for a while, we knew it was time to let go. I spent a year without seeing anyone and recently started dating again. You can read part of my crazy story here hahaha
    Love how you write! I enjoy reading your blog very much Danielle!
    Have a great day and thanks for sharing!