How to know when it's time to end things with your situationship

Six questions to ask yourself if things just don't feel right

Having been dumped on the street after a wedding, I understand just how tough a breakup can be. If you’re grappling with heartbreak, here's how to navigate moving on effectively.

I've also been on the flip side, ending relationships with boyfriends, situationships, and even Let’s Fucking Date contestants. While breakups can be devastating, breaking up with someone can sometimes be even more challenging. When you're the one initiating the split, you face a different set of anxieties and fears, like “Is this the right choice?” or “Am I making a mistake?” The thought of “starting over” can haunt you, making it easy to idealize the relationship and delay the inevitable.

What has always guided me is knowing the kind of relationship and partner I want and not settling for less. If you’re interested in learning more about that, check this out.

So, that leads us to the timeless question: “How do you truly know when it’s time to end things?”

I want to acknowledge that this question has very different answers depending on if you’re in a) a situationship or b) a relationship. So, I’ve broken it into two parts, starting with…

How to Know When It’s Time to End Things With Your Situationship

Let’s dive into those relationships that lack a clear label—yes, I’m talking about your situationship. We’ve all experienced that unsettling feeling that something’s off with the person you’re seeing.

Perhaps things aren’t progressing as you hoped, and you're tired of waiting for change. Or maybe you’re hesitant about taking the next steps. It’s like the uneasy feeling after an awkward job interview, where you’re left wondering if they see you as a good fit or if they want to move forward. Sometimes, it’s not that anything’s explicitly wrong; it’s just that it doesn’t feel quite right. You might be comfortable, but are you truly satisfied?

There’s a common myth that a situationship will naturally evolve into a full-fledged relationship—spoiler alert: it won’t. From my own dating experiences and those of my friends, I’ve seldom seen a situationship magically transform into a committed relationship. 

If you’re unsure whether you’re in a situationship, ask yourself these six questions:

1. Do you feel safe? 

A good friend of mine, Natasha Parker, once told me that to truly connect with someone, you need to feel safe. Reflect on whether you’re constantly editing yourself—your tastes, texts, or schedule—to fit someone else’s expectations. I can’t tell you how many times I would send a text message response hours later because I was afraid I would say the wrong thing… or how many times I was left alone and sad without plans because I would leave nights open in case the guy I was seeing texted. If this resonates, it’s time to let them go. It’s not about your anxious attachment style; it’s about finding a partner who helps you work through it.

2. Are they ready to commit?

If you’ve been dating for over three months without clarity on your relationship status, it's time for a conversation. If you’ve expressed your desire for something serious and they either decline or dodge the topic, consider it a sign to move on. If they explicitly state they're "just looking to have fun," thank them for their honesty and make it clear that you're seeking a committed relationship. 

Specifically, you can say something like this:

If they give you a hard time or try to gaslight you (like call you dramatic), you can say: “I respected your decision and now it's time for you to respect mine. 

BTW, if being transparent and protecting my time and energy is considered “dramatic” then I guess I’m the biggest fucking drama queen out there.

For my paid subscribers, below are four more critical questions to ask to get to the bottom of things, as well as an important lesson I learned from that time I dated an actor/Soulcycle instructor, lol

3. Does the relationship feel one-sided?