How to Navigate Key Relationship Milestones

This article is an excerpt from the Shortform book guide to "How to Not Die Alone" by Logan Ury. Shortform has the world's best summaries and analyses of books you should be reading.

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Are you the kind of person who prefers a relationship to develop organically? Or do you intentionally decide whether, when, and how to move to the next stage?

When it comes to moving to the next relationship milestone, there are two kinds of people: People who reactively “slide” into the next stage without giving it serious consideration and people who consciously “decide” to move into the next stage. In the long run, deciders tend to fare better.

In this article, you’ll learn how to decide well at turning points in the relationship: defining the relationship, cohabitating, and getting married.

How to Navigate Defining the Relationship

How can you ensure that you actively choose to define relationship milestones? Ury recommends that you first discuss your expectations for the relationship when you want to be exclusive. Exposing your feelings can be scary, but making your wishes clear will save you potential heartbreak long-term (if your desired partner doesn’t see you as long-term material). And even if your conversation doesn’t turn out the way you hoped, you’ll have more information to help guide you on your partner search—whether that means continuing to date this person or moving on to someone else.

(Shortform note: Other relationship experts have more specific recommendations for discussing relationship expectations. Prior to the conversation, remind yourself that it’s OK to pursue your desires, which can help ease your own fears. Then, select the right time to have the conversation; don’t initiate it because you’re frustrated that the other party hasn’t made their intentions clear. And no matter the outcome of the conversation—whether you choose to date each other or see other people—congratulate yourself for putting yourself out there.) 

How to Navigate Deciding to Cohabitate

How can you ensure that you actively choose to cohabitate? Ury recommends that you seriously evaluate whether you want to cohabitate. People who move in together pre-marriage are more likely to get divorced, which relationship researchers theorize is because cohabitation makes splitting up harder: When a breakup involves someone moving out, it’s easier to ignore the nagging feeling in the back of your mind that you’re with the wrong person and slide into marriage instead. 

To minimize the chances that cohabitating jeopardizes your relationship, Ury recommends that you discuss your expectations about the future with your partner to ensure that you’re in sync. Additionally, discuss any anxieties you may have about cohabitating, like a worry that you won’t get enough alone time, so that you can work through them and set up a plan to deal with them prior to moving in. 

How to Navigate Deciding to Marry

How can you ensure that you actively choose to get married? Ury recommends that you critically examine your needs and wants prior to getting married. Humans are subject to a consensus bias: We assume that other people want and believe in the same things we do. But this bias is dangerous. It can lead us to marry people without discussing important topics because we assume they agree with us—then later end up being unpleasantly surprised. For example, you might assume that your partner wants to stay home after you have kids, only to learn that they want you to stay home instead.

To avoid the marital dissatisfaction that can stem from the false-consensus effect, Ury recommends sharing both your history and your expectations with your partner. Once you’ve determined that your partner is someone who can support you and improve your life long-term, sit down with your partner to discuss three important topics. 

Dedicate one night to learning about each other’s history, like how your parents dealt with serious topics or important childhood events. Dedicate a second night to discussing how you are now: Talk about how you could improve the relationship and open up about your current financial situation. Finally, dedicate a third night to discussing your future expectations, like your long-term career goals and how you want to raise your children. Ury explains that it’s OK if your expectations don’t exactly align, as long as you can talk through and have a plan for dealing with them. 

How to Navigate Key Relationship Milestones

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Darya Sinusoid

Darya’s love for reading started with fantasy novels (The LOTR trilogy is still her all-time-favorite). Growing up, however, she found herself transitioning to non-fiction, psychological, and self-help books. She has a degree in Psychology and a deep passion for the subject. She likes reading research-informed books that distill the workings of the human brain/mind/consciousness and thinking of ways to apply the insights to her own life. Some of her favorites include Thinking, Fast and Slow, How We Decide, and The Wisdom of the Enneagram.

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