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How to Embrace Uncertainty in Dating and Relationships

anxiety dating relationships Aug 08, 2021

I finally arrive at work after an arduous, 75-minute commute. After taking off my winter coat, scarf, hat, and gloves, I refill my tea. Settling in at my desk, I pull out my laptop and log in to the network. First, I check my schedule and see that I have back-to-back meetings for most of the day — ugh. I see an email from my boss. He needs information for a quarterly business review. The email has a red exclamation point, marking it as urgent. I start to respond, but then I remember an even more pressing matter that needs to be addressed.

I open up my spreadsheet. Each row represents every day I have seen my boyfriend — ever. It goes back to before we were even dating, when we would meet for coffee after a yoga class. I saw my boyfriend last night, so I put an “X” in the column next to today’s date. We had sex, so the next cell gets three Xs. If we merely kissed, I would have entered two. One X means that we saw each other, but there was no physical interaction. Luckily, this doesn’t happen often. In the activity column, I select what we did from the dropdown. For example: dinner, a walk, a yoga class, etc. I created a dropdown so I could sort it all later — freeform text is not great for data analysis. However, there is a notes column where I can add any concerns I had about our interaction.

My therapist tells me that this tracking behavior is a sign of relationship OCD and not very healthy. She suggests I stop. While I tend to agree regarding the health of this habit, it seems like a shame to stop now — there is so much data; surely, it has some useful purpose. Now, I can calculate trends: Do we see each other more or less? Are we having sex more or less often? What days of the week do I see him most? I could create my own quarterly review for our relationship, tracking its health with a color-coded system. I could share it with my boyfriend so we could talk through strengths and opportunities. We could always be aware of the well-being of our relationship, at any given time. I think it’s genius. If I had more time, I would create a relationship analysis app.

That was my morning ritual for the first year of my relationship with my boyfriend. I was often wracked with anxiety, trying to figure out where things were headed and attempting to assure myself that the relationship was healthy. Ironically, I also realized that tracking each interaction was very unhealthy behavior. Despite the positive trends, my data showed me, I continued to feel anxious and uncertain about where we stood. I was looking for quantitative evidence that everything was going to be okay or, more specifically, that I would be okay. Of course, when it comes to relationships, there are no guarantees.

No one wants to be another’s life raft anchored to a mooring.

Let’s consider more data. We know that about half of all marriages in the West end in divorce. It almost seems suspect that any rational human would choose to get married, knowing it was a coin toss as to whether they would stay together or need to embark on a costly and mentally arduous legal process to divide assets and children. The odds just aren’t very good. Moreover, we don’t even know if the remaining 50% are happy. Yet, despite the data, many of us continue to get married or form long-term partnerships.

We have a primal desire to connect with others and be accepted. We are designed to pass our DNA to the next generation, so our species continues to survive. We are born to connect and procreate. That’s likely why we sometimes feel that we need a partner to survive — it’s in our biology. My spreadsheet was an attempt to confirm my likelihood of survival.

Luckily, our survival is no longer a threat and should not be a factor when considering or maintaining a relationship. In fact, going into a relationship with a life-or-death attitude is not an effective strategy for building a healthy, interdependent partnership, where both individuals have space to grow and evolve. It’s a recipe for codependency and resentment. No one wants to be another’s life raft anchored to a mooring.

Based on my behavior — and what I hear from others — it appears we could be overcomplicating our relationships. What if instead of approaching relationships as dire endeavors, we approached them with playfulness, grace, and curiosity? Rather than looking for evidence that it will be a success, or for red flags indicating that we should jump ship, we look instead to how we feel in the present moment? We could ask ourselves questions like:

  • Do I enjoy spending time with this person?
  • Do they make me want to be better?
  • Are we honest with each other?
  • Do we have each other’s best interests in mind?

Since we can’t predict the future, these questions would at least give us an indication of the quality of our relationship right now.

Past trends are not indicative of future performance.

Instead of treating our relationships like a game of Battleship, where we keep our agendas hidden as we wait for our partner to make one wrong move, we can act more like we’re playing Candy Land. We move forward with enthusiasm, even as we know there’s a chance we may have to go back to the start. We don’t know how the cards are shuffled. It’s not a huge surprise when we encounter detours — and yet, we still enjoy the game. There is an energy of playfulness.


Since my spreadsheet did not produce the calming effect I had hoped for, I eventually gave it up. I decided to take a different approach. Instead of relying on data to provide me with information on my relationship’s health, I looked inward. I asked myself how I felt when I was with my boyfriend. And rather than look to the data to determine his feelings toward me, I would (gasp!) ask him how he felt. I stopped relying on data and started relying on communication. Moreover, I began to understand that no matter what happened in the relationship, I would survive.

I still wondered whether fickle, subjective, messy human emotions could be a better guide than quantitative metrics, but I quickly realized that they are a better indicator of how things are right now, in this present moment. On charts that map stock market performance, there is often a disclaimer at the bottom that reads: “Past trends are not indicative of future performance.” The same is valid for relationships. Once I deleted the spreadsheet that enabled me to look at past trends so I could attempt to predict the future, I started to enjoy the relationship as it was right now. Even though I can’t say with certainty what the future holds, I have faith everything will be fine — one way or the other. I’ve developed grace.

Our expectations become limitations.

Sometimes we get tunnel vision and become laser-focused on a particular outcome. Unfortunately, we don’t know whether a specific outcome will bring us happiness or not. (Remember: 50% of marriages end in divorce, and I’m pretty sure that wasn’t the couples’ intent.) It reminds me of the quote from Kurt Vonnegut: “The truth is, we know so little about life, we don’t really know what the good news is and what the bad news is.” If we take a broader perspective, we see there are more options available to us. Our expectations become limitations. Instead of focusing on a singular outcome, we can become open-minded and curious to see how a relationship will evolve. If it doesn’t work out, we can assume there’s something even better planned for us.

I try to remember that now. Sometimes I become hyperfocused on when my boyfriend and I will move in together. There are a few things that need to happen first — like building an addition on the house and ensuring my kids are on board. (You know, small things.) I can sometimes feel like this is the one thing standing in the way of me and eternal happiness. Though, really, I have no idea how living together will affect my happiness. Maybe it won’t be as fun as I imagine. Now, rather than force it, I try to enjoy the present and remain open and curious to all possible outcomes.

When I’m not looking for key indicators by which to evaluate my relationship, I’m happy and content. My relationship feels secure and supportive. I don’t try to force situations or passively remain silent, expecting my partner to read my mind. I can communicate my needs and desires and give my partner the space to figure out if, and how, to fulfill them. I don’t need to direct him. Without a detailed plan, there is room in our relationship for surprises, spontaneity, and growth.

Your survival is not predicated on the success of your relationship.

Now, you might be saying to yourself, “Sure, that sounds great and all — but how do I let go of my need to predict and control? My mind is a strategic battlefield.” Trust me, I hear you. Here’s what worked for me:


Create a relationship gratitude journal or note pleasant dating experiences. If you’re in a relationship, start a gratitude journal about all of the things going well in your relationship. Focus on the positive and what you have rather than what you are lacking. You will start to appreciate all the great things about your partner and might even realize that you don’t actually lack anything.

If you’re dating, start to note pleasant experiences. Even if it is not a match made in heaven, you had an interaction with another human being. What did you learn from the encounter?


Our minds shape our reality. We need to be able to observe our thoughts without fusing with them. We need to be able to catch ourselves when we obsess over “what if” scenarios and redirect our focus to the present moment. The best way to do this is through a consistent meditation practice. Even five to 15 minutes a day can help you realize that you are not your thoughts, and you have power over where you focus your attention. Where attention goes, energy flows. Be thoughtful about where you put your focus.

Get vulnerable

We try so hard to make sure that we won’t get hurt or disappointed. But of course, there will be times when we do. Only, if we don’t communicate our needs and feelings with others, not only will we experience hurt and disappointment, we will also feel remorse that we didn’t express our truth. Remember, we all have insecurities, fears, and a desire to be liked. When we get vulnerable and share our needs with others, we create an intimate connection. Even if our feelings aren’t reciprocated in the way we hoped, we still retain power because we were honest. There is power in our vulnerability when we choose to reveal it.

Change course

If you’ve communicated your needs and they still haven’t been addressed, you have two options. You can fulfill your own needs, or you can change course. This is not about sticking with a relationship that is not fulfilling. It’s about accepting it as it is and making decisions based on how you feel in the present. I sometimes hear people say, “We’ve been together for five years. I don’t want to give up now.” I’ll respond with another stock market example (I was in financial services for a good part of my adult life): You sell — not hold — your underperforming stocks. Be willing to wish others “Godspeed” on their journey and to continue on your own.

Take a deep breath. Remember, your survival is not predicated on the success of your relationship. It’s not your responsibility to predict and control it. Save yourself the effort and watch as it divinely unfolds with playfulness, grace, and curiosity.


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