Relationships are hard.
How do you know when it’s time to let go? When to try again? Especially when you’re young and growing, changing, figuring things out constantly.
Regardless, getting back with an ex often incites a lot of judgement and can cause the people involved to isolate themselves. Sometimes though, both being apart and being together feels wrong.

Advice for friends
If you are the friend of someone dealing with an on and off relationship, my first recommendation is that even if you have to emotionally detach, try and listen to them when they need it.
Give them the hard truth but try to show compassion too. If they lose all avenues to vent, it will pull them closer to the person. The risk of them losing themselves completely becomes significantly higher. At the end of the day, people will do things in their own time.
You also will not know the complete ins and outs of the relationship. It is natural for people to turn to others to vent: understand that you probably heard the worst aspects of the relationship, in the most negative possible version of events.
There are many reasons your relationship might be stopping and starting:
- Incompatibility: You have great chemistry but you can’t stop arguing over big issues. You keep telling yourself things will be different this time so you try again.
- Not knowing what you want: So you think you love this person but there are things making you unsure so you end it. Maybe you are wondering if there is someone out there better for you. Then, after a while, you miss them so you call them back in hope that things will be different this time. You are still unsure and the cycle continues.
- Toxicity: Maybe you don’t want this person but you also don’t want anyone else to have them so you keep them on a string. Maybe you can’t seem to let this person go so you cling on too tight and lose your respect in the process.
- Life challenges: It could be physical distance, it could be that you want to focus on other things: making friends, career or some familial issues which put temporary emotional strain on the relationship. When these are overcome, you are ready to go back.
- A combination of several.
My advice:
The first step is to identify the reason things keep ending. If it’s toxicity then you need to give yourself an intervention. There is no good reason to return.
The others are more complex... They ask the question:
What is the difference between giving someone another chance and disrespecting yourself?
Only you hold the answer to this.
Romantic relationships are deeply personal. Nobody else - not your closest friends, not your siblings, not your parents, and not theirs - nobody else knows them in the way that you do (as they shouldn’t). So only you can decide if they deserve another chance. Or if they are right for you. They can provide insight which shouldn't be ignored but ultimately, it is up to you.
My general advice is to be kind but honest to yourself. If you have gotten back together and broken up in a short space of time, realistically will giving them a third chance reap any different results? If the answer is a solid yes, go for it.
However, I would say that this seems unlikely. In which case, it’s time to let go.
I think in the majority of cases two chances is respectable but a third one is signing yourself up to the circus.
Now, what if a lot of time has passed since the last on and off situation occurred?
I think to shed the baggage of an intense relationship it takes years to have grown enough as people for the dynamic to have the potential for real change. The bottom line is that there will be resentments if you had tried and failed to make it work. It is essential to let them go, to let go of the resentments too. If you have truly grown and moved on, you should be hesitant to give each other another chance. It didn’t work before so why now?

A chance meeting likely reaps a higher probability of it being a successful re-connection than if one of you is orchestrating it. Someone orchestrating it implies that they are still clinging onto the past in some capacity.
Regardless, now you need to evaluate. Did you harbour a good friendship whilst you were in the relationship? Did you fundamentally get along? Is there a chance that your past issues will crop up again? Have you released yourself from any past resentments? Had you both really let go of each other? Will it truly be a clean slate?
If your answers to these questions are positive, why not give them a chance? If you’re both considering it, there must be a reason. Maybe it was a case of poor timing in the first instance. However, take it slow. Gradually rebuild and be wary. If there is any evidence of old habits resurfacing, be prepared to let go again and quickly. Once you are certain you have a fresh start without old bad habits or resentments creeping in, let yourself be happy.
Conclusion
Matters of the heart are complex. Sometimes you need to go through things for yourself; give too many chances, go back one too many times. There is no judgement if you don’t follow this advice. Every case is truly unique. At the very least it’s a life lesson learned.
I will say, if things feel wrong, they probably are. It is cliche but focus on yourself, your worth and what you really need out of a relationship. Be honest with yourself about when it’s time to stop and let go.
If you find yourself in a constant string of on and off again relationships, please ask yourself why? Do the self work to fix it. You will either attract bad people or lose good people through the continuation of this.
The bottom line is, if someone isn’t sure about you, if you aren’t sure about a person, you must let them go. You cannot keep going back.
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