Should I stay or should I go? 10 meaningful questions to ask yourself

Should I stay, or should I go? Do I actually want to spend the next 2-5 years with that person? What about 30 years? Are they going to support my growth? And about change, what if we grow apart? 

It can be so confusing, especially while looking for “the one,” but casual dating makes no exception, really. 

I remember that whenever I met someone new and attractive, I had to figure or so much while also trying to look charming and bright and balancing my other relationships if I had some.

What a mess! 

I finally sorted this out by using the best life advice I ever got. It comes from Neil Gaiman in his famous “make good art” address. This commencement speech is intended for artists, but there is some insight into life that is GOLD. Trust me, I’ve been sending it to EVERYONE for the past six years.

The idea is to picture where you want to be as a mountain. And whenever you have a big decision to make, you can ask you if it brings you closer or further away from the mountain.

I’ll drop the full speech at the end of the post but stay with me for now 🙂

Relationship as an agreement

First and foremost, we have to discover your mountain (i.e., your dream relationship). Because any partnership is a contract you make with each other. Every party agrees to bring something and to get something in return. You give time to your boss in exchange for a salary. This is kind of the same.

We think a couple is a very specific kind of partnership implying a particular “couple contract” that is universal and should be respected by all world lovers. Still, not all lovers live together, have sex, get married, are exclusive, or have children. Not all couples decide to put the relationship before an exciting job opportunity. Some people put their family first and their romantic partner after. Some do it the other way around. 

So no, forming a romantic relationship is not something that “just happens naturally,” and for the sake of feeling safe and secure, you might want to get clear on what you want and make sure that you can get it.

You may not have the luxury to choose all of the contracts you enter (or quit!) in your life. You may not be able to choose your family, negotiate your rent, or successfully object to Facebook’s privacy policy.

But you probably can choose your relationships.

What do you want?

I know what society is telling you. You’ve seen the romcoms. Guy meets girl; they fall in love, almost lost each other due to some misunderstanding, and then after some grand gesture, they move in together, get married, and have two kids.

In some cases, the gender of the protagonists may vary, as does the number of kids.

With a patch that seems so straightforward, no wonder a lot of us don’t even bother to discuss as a couple what we want our future to be.

But as you probably know, there is a broader range of relationships than the ones deemed “relatable” and worthy of representation by a TV producer.

That’s why I would love for you to take a few moments to reflect on what *you* want, so you can then orient yourself towards your mountain.

You may not have an answer to all of the questions below, and that’s fine. But if you DO have a strong preference, make sure that you are honoring it as much as you can.

  • What do I want to get from a relationship? Think love, safety, support, someone to share Sunday brunch with. What really matters to you?
  • Is it important to me that the relationship lasts? How long? We have a strong tendency to measure relationships to their duration, and it might be a mistake. Of course, it’s nice when a good thing lasts, but the love, healing, support, personal growth, memories you get with someone won’t vanish once the relationship ends.
  • What is my definition of a happy relationship? What would be some key indicators that we are happy together?
  • How do I feel about children, cohabiting, getting married? Think about the significant relationship steps that you hope to live… or would prefer to avoid.
  • How significant should sexual intimacy be?
  • What is my definition of fidelity? You can be faithful to all sorts of vows and agreements. Make sure you enter one that works for you and that you do it in good faith. 

So you have your mountain! Now you can always check if your journey is going in the right direction. It’s okay to take breaks and to enjoy the scenery, though. Remember that ide and relationships are a journey and that there is always something to learn.

But just to be safe, I wanted to give you some pointe for the relationship you are in.

Do you need to change the container of the relationship?

Maybe you two are perfect for each other but seeing yourself so much makes your “island” personality get anxious. Perhaps not knowing when your next date will be is making you feel anxious, and it is not for you to “go with the flow.”

A healthy conversation on the container right now will benefit you both, and it could avoid a lot of troubles down the road!

Are you getting your needs met?

Your lover/spouse is not in charge of your satisfaction in all areas of life; you are. But some relationship needs are really fundamentals and should be honored.

Think about safety, compassion, love. Does your partner make you feel safe? 

And if your partner is not meeting your needs, could you ask for some specifics action they might take to help you feel loved and secure? Like cooking for you once in a while or taking care of the kids so you feel very supported and you can hang out with your friends. Be as specific as possible and don’t think your partner can read your mind and guess what you want. It’s so much easier and empowering to just ask.

Is this good for you?

Think higher purpose. We don’t all have a clear-cut goal in life, but if you have one, it’s time to get very real with your priorities. Can you have your dream/goal and be in this relationship? If not, it’s time to get very real on what you want to prioritize today.

You can also ask yourself if you feel good at all. Obviously, relationships are work, and you won’t probably feel blissful all the time, but if it is aking you miserable on average, why are you keeping choosing this?

I hope you feel empowered to have meaningful conversations and to take your relationship to the next level, whatever that is for you.

Love you so much!


  1. Oh yes. Nice article. I send it to my friend. He might need this. Just sayin’

    1. awwww! I’m so happy I can be of service, thank you Marcy!

Leave a Comment

Your email address will not be published.