If you’ve been in an on and off relationship that has seen more than one round of the breaking up and making up cycle that so many relationships seem to fall into, it can be hard to know how to proceed in that relationship and how to actually progress and make things better in a way that allows you to to embrace the good parts of your relationship while leaving the bad parts behind. But, if you have had an on again/off again relationship with your current honey and one or both of you is seriously considering taking your relationship to the next level and getting engaged, then there are definitely some things that you should carefully think over before actually taking the dive into betrothal and eventual marriage. So, what are the most particularly important things to keep in mind for on/off couples that are edging their way towards engagement?

10Why Hasn’t It Worked Before

No one has a perfect relationship and everyone encounters issues at some point, but what you need to ask yourself is if the problems that you have are problems that can be overcome or if they’re fundamental incompatibilities between you both. If you’ve broken up before then there are clearly some issues that need to be resolved between you both, and if you’re serious about getting serious then you need to take a long and detailed look at exactly what made your relationship fail before and ask yourselves if those failures are legitimate relationship conflicts that can’t be fixed or solvable problems.

9Have Your Relationship Problems Actually Been Solved

All relationships have problems, and if you’ve been on and off with a partner then there are reasons that you kept on separating from one another but there are also reasons why you kept coming back together.

Obviously you have something good together if it continually brings you back, but if you want to get serious and have a legitimate life long partnership then the problems that split you up in the first place have to actually be resolved. Love only gets you so far, and if you want to get engaged then you need to get through your problem solving first.

8Do Your Life Goals Line Up

Taking both of your individual life goals into account and how those goals can blend together is something that every single couple needs to seriously think about before they decide to get engaged, but this is an especially important consideration to take into account if you’ve broken up before. It needs some extra attention in this circumstance simply because it’s clear that your trajectories in life have conflicted enough before that you actually got to the point of breaking off the relationship, and if you want to get as serious as a relationship can get then you need to make sure you’ve gotten on the same page here.

7Do You Want A Wedding Or A Marriage

The wedding industrial complex has become a complete monster of our society, so it’s unfortunately very common that people want to get married simply for the sake of having their wedding and showing all of their friends and family that they’ve essentially leveled up in life. And so much thought and preparation can go into a wedding that the people getting married can sometimes lose sight of the fact that they’re actually going to be married after all is said and done, and sometimes that means a couple is woefully unprepared for married life.

If you want to get engaged to your on and off, you need to think about whether or not you’re truly prepared for marriage.

6Are You Getting Engaged To “Fix” The Relationship

You would think that after a nearly 100% failure rate for pretty much the entire history of relationships people would stop trying to take their relationships to a higher and more intense level in an attempt to fix the relationship, but it’s pretty much a guarantee in life that at some point you might want to intensify an already failing relationship in order to try to make things better.

And on the surface it might feel like you’re really ready to take things to an engagement level, but you need to reflect on the relationship and really ask yourself if you’re doing it because you think it might make a bad situation better.

5Are You Sure

If you’ve been in a relationship that has broken up before then that certainly doesn’t mean that it’s going to break up again, and you can separate and come back together and wind up staying in a happy and healthy relationship for the rest of your lives. However, the reality of the situation is that at some point your relationship had deteriorated to the point that one or both of you decided that you needed to break up. And you both got back together because you ultimately wanted to make things work, but you need to consider whether or not you want the engagement because you truly want it or if it’s just because you want things to work.

4Is The Engagement Controlled By Outside Circumstance

Obviously if you’re considering marrying your partner you should consider how your lives are going to mesh together and what kind of progress you both want to be/feel like you should be making, but you also need to think about whether or not your engagement is being completely driven by those things. People can experience a lot of pressure from their families, friends, and co-workers to advance their relationships for a lot of reasons, and the pressure to settle down and start a family themselves can really affect people. So you need to seriously ask yourself if you want to get engaged simply because your relationship “should” be progressing that way.

3Have You Stayed In The Relationship By Default

Sometimes on and off relationships are on and off because the people involved just have trouble communicating with one another or getting on the same page, but other on and off relationships are on and off because the partners in the relationship are just uncomfortable with the idea of moving on.

It’s actually pretty common for people to stay in relationships longer than they should just because they’re comfortable with staying the same, but there is a big difference between prolonging a relationship because of comfort level and actually advancing a relationship to the point of engagement because of comfort level.

2What Makes Things Different Now

If you’ve had an on again/off again relationship with your partner then it’s safe to say that there are at least very strong feelings there that neither of you can, or wants to, deny. But as you’ve probably learned by now, just having very strong feelings for someone is no guarantee that your relationship will last in the long term, and if any relationship that has broken up in the past is going to last now then something has to have changed from the last time that it broke up. So if you’ve gotten back together without making any serious changes, then you really need to work on that before getting engaged.

1Are We Both Ready

To be honest it can be incredibly difficult to know if you’re really ready to marry your partner, even when your relationship has been stable and consistent. Marriage is, or at least should be, the most stable state you can ever have in any relationship, so if you don’t have a solid foundation of stability already then it’s very possible that you’re simply not ready to be married yet. Obviously if you really want to be together forever then that’s a good starting point for marriage, but if you think that your feelings about that could change again then it is a decidedly bad starting point for marriage.


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