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How to Have a Milestone Conversation: Creating Safety

Updated: Sep 27, 2019

by Kristal DeSantis, LMFT

Did you know that if you live together with a partner before you get married, you are more likely to get divorced? Sounds surprising right? You might think that living together before marriage is an excellent way to determine if you and a potential life partner are compatible. When you live together with someone, you find out a lot about who they are and what they are like in their private moments. Living with someone is like getting a "behind the scenes" look at who they are. You would think it is a pretty good sneak preview of what your life would be like together. So why do the statistics and research say otherwise?

Well, in the same way that a ball rolled down a hill gets faster and faster, when a couple starts dating, their "relationship momentum" gathers speed as well. When a couple is in the beginning stages of dating there are lots of "milestone moments." These are moments that mark the journey towards commitment. These moments push the relationship along; they give it more speed. Examples of these milestone moments might start with: "Wanna hang out?" and progress to "I really like you," I want you to meet my friends," to eventually "I love you."

"Let's move in together'' is another significant milestone moment in a couple. However, as a relationship naturally gathers speed, sometimes the relationship ball rolls a little faster than the couple can keep up. There are times when moving in together happens before a couple is genuinely ready. Often the "let's move in together" conversation never actually happens. But the moving in does. Once a couple moves in together, the desire to have more Milestone Conversations tends to slack a bit. "What else is there to say? We're already living together! We'll figure the rest out as we go along." The trend can then start to drift more towards stagnating comfortability in a relationship rather than intentional stability. That is where the statistics show that couples who are living together aren't necessarily on the same page about their relationship. They've just "slid into commitment" without having the Milestone Conversation to ensure that they want to be that committed.

There is a quote which says,

“Avoiding difficult conversations is trading short-term comfort for long-term dysfunction”.

And this is absolutely the truth. Milestone moments are great opportunities to have Milestone Conversations. This helps to ensure that partners are ready to take the next step and are on the same page about moving the relationship forward. The better you get at intentionally communicating before taking big relational steps, the better off your relationship will be in the long run. However, these conversations often come with high stakes. It is totally understandable that it can be hard to approach them. How can you ensure that you get through it successfully?

We’ve gathered some tips for you around creating a Safe environment to ensure you and your partner are set up for success. Follow these four steps and start having these Milestone Conversations!

1) Set the Scene: Environmental Safety

Timing and atmosphere are crucial. Make an appointment to have this conversation. Don't just spring it on your partner at the end of a hectic workday or when you are out in a chaotic place. The environment will play a role in how successfully this conversation goes. Pick a time when you and your partner are both in a good headspace with plenty of emotional bandwidth available. Find a setting that is peaceful, quiet, and non-triggering. It has been said that the scariest words in the English language are "we need to talk." When you pick a date to talk with your partner, let them know that you have something important to say. But, if you can also reassure them that significant doesn't mean scary, so much the better.

2) Know Thyself: Body Safety

Do you know what your body does when you are anxious? Can you recognize when you are getting upset? Do you know your markers of getting activated into "fight or flight" mode? Or, maybe you're a "flop and freeze" kind of person in a stressful situation. Who knows? Hopefully, you do! Everyone has a "window of tolerance" for stressful events, and sometimes a deeply emotional conversation can be a bit stressful. Pay attention to how your body is responding to the conversation so you can ask for a break or a hug when you need it. When you know your window of tolerance, and your partner knows theirs, you can work together to ensure both people stay present and connected through the conversation.

3) "I feel": Emotional Safety

When having a Milestone Conversation, speak from your feelings and emotions, not "shoulds." It isn't always easy to have a conversation discussing a milestone in your relationship. It can be even harder to speak from your honest emotions. Sometimes it can be more comfortable to speak in "shoulds." I.e., "Well, I think we should move in together since we're wasting money on rent."

However, this is doing both you and your partner a disservice because "shoulds" take your power away and gives it to an imaginary relationship rule book. Its YOUR relationship. Own it! Say it! "I feel like taking the next step in our relationship. I want us to move in together. What are your thoughts and feelings about that?" Vulnerable sure, but also honest and empowered. Emotion and feelings bring people closer together and creates connection in a shared experience. “Shoulds” can take the conversation into debate territory, which is not connective at all.

4) Boundaries and Needs: Relational Safety

What are your needs moving forward? What are your limits? Do you have any deal breakers around this issue? If you do, can you articulate them to yourself and your partner? Often when these big "booster moments" happen in a relationship, people are moving at different speeds, and that's ok! You are two separate individuals; it makes sense if you are not exactly on the same page at all times.

Having a Milestone Conversation allows each partner to let the other know where they are in the process of commitment. Are you just now thinking about it? "Traveling abroad together? I honestly never considered it until now." Maybe you're on the fence. "Hmm, I would like to date you exclusively, but there are a few things I'd like to discuss first." Or, perhaps it's all systems go: "Moving in together?! Yes, please!" Checking in with yourself and your partner about boundaries and needs is also a good way to ensure that when you take the next step in the relationship, it is an informed step forward.

Creating a safe environment, knowing your body cues, coming from an emotionally honest place, and knowing your boundaries are crucial elements to a successful outcome to a high-stakes conversation. Following these four steps to create safety in conversation will help ensure that the scene is set for both partners to be honest, open, and take intentional steps together towards a STRONG, long-lasting relationship.

Stay tuned for part 2 of Safety in Conversation: Getting on the Same Page


If you and your partner are struggling with having Milestone Conversations on your own, we are here to help! Sometimes beginning with a trained therapist who can help guide you through these steps can give you the confidence to do it on your own. Check out our team and book a free 15 minute consult with one of our therapists. It's never to late to learn new relationship and communication skills and start having those conversations!

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