Do The Rules Of Dating Change As We Get Older?

The answer is YES, here’s why.

Last week. Over the phone. The topic of hard conversations (and how to have them) came up with a girlfriend. "How do you feel about asking the "big questions" when you're newly dating someone?" she asked. "Things like: do you want (more) kids; do you want to stay in this city, etc?" She continued, "For yeeaaarrrs I’ve been "playing it cool" so as not to seem eager, but I just don’t have the time to waste anymore."

"Yes. Without a doubt. Ask the questions," I said. "If you're into someone, why wait to find out if you're compatible? As we get older, the idea of "playing it cool" simply doesn’t work. At this point, we know what we want, what we don't want, what we're open to discussing, and what's a non-starter. Share it all. And not for nothing, but often leaning into the uncomfortable (with the right person) can actually make the relationship stronger.”

Jumping off the phone, I took it to Google: should you have hard conversations early in a new relationship? In big, bold letters, the internet returned the word YES. And then it continued: don't avoid the hard conversations; they often lead to a closer connection when you get to the other side. See, even Google agreed. Next time I'm going straight to ChatGPT.

Of course, none of this used to matter. At one time, marriage was practical, not romantic. Everything was preordained. You knew what was expected of you, how to behave, and where you'd live. The surface was calm. Everyone played a role.

But that's no longer the case (in most places). We now have all the freedoms, and with that comes an overwhelming amount of choices that have dramatically altered the relationship field. What was once defined by rules, duty, and obligation now occurs through conversation and open dialogue, making everything a collaboration (and sometimes even a negotiation).

So perhaps the real story here is that all stages of dating, marriage, life, and love are active understandings that call for constant conversation, negotiation, and flexibility. Think about it - you and your partner need to decide together about where to live; whether to have children, how many, and if this is the right time to have them; whose career is prioritized; what are we spending money on, and who pays for what; how to parent or step-parent, and organize custody schedules; what to eat (sushi or Italian, I mean, there are no other options) and do we go out or stay in. A growing chorus of objectives that ultimately make up life's nuts and bolts. And, as we get older, many things are either hard-set, like career, location, kids’ schools and custody arrangements, or need to be decided from the onset, like having kids or being vegan (idk, you fill in the blank). If you're newly dating - especially in the early days when everything is fun and easy, the sex is amazing (if we're being totally honest), and you want to seem impossibly effortless, it can be awkward to raise such topics. But some things can't wait.

A few days later, I had coffee in LA with another friend. She recently started dating a guy with a teenage daughter. After not-so-many dates, she opened the "to baby or not to baby?" conversation with him to avoid going all in if he's not interested in having another child (or children). Fair. Time is precious.

In my relationship, we had the same conversation after a few dates. In our case, though, neither of us wanted more kids, given that we already have three near-teens between us. But, had we not been on the same page, it certainly would have been better to know that sooner rather than later. And since then, we've had many more "foundational" discussions (as we've grown together and chart our course), that we often "check in" on to make sure we still see it the same way.

And yet, another girlfriend, who has been married for 20 years, asserted that it's never too soon to have the hard conversations, whether you are 22 or 52. Speaking from the experience of her own multi-decade marriage, she believes that even in your 20s, you need to be (and remain) in lockstep with your partner on the big stuff; otherwise, you end up years down the road with disparate views on family and married life.

Hearing her say that made me wonder: even if you are aligned on a path, nothing is a given, and life rarely executes to plan (as they say, best-laid plans). Therefore, how do you account for a partner changing their mind? Or allow for life's many curve balls or the complicated reality of dating a divorcée? For example, you might "plan" to have two kids, but time only allows for one, or your partner decides they really don't want another, or you might "plan" to live here and end up there, or this career becomes that, and so on. And while there's so much beauty in the unexpected broken plan that takes you off course and onto a path you could never have imagined, it also requires a significant repatterning of ideas. I think about this all the time. In my former life, I was set on becoming a mom of two, but as life would have it, I'm a mom of one remarkable human with two other wonderful children in my life and endless incredible experiences that I otherwise may not have had, had my life gone according to "plan." Therefore, being open to the unknown or a shift in the plan could lead to something extraordinary that you can’t even imagine. That said, where's the middle ground between following a plan and allowing for possibility?

I recently read an interview with Esther Perel, in which she says love is a verb (this goes for relationships too), an action, a practice, a dynamic bond. She says, "It's an active engagement with all kinds of feelings—positive ones and primitive ones and loathsome ones. But it's a very active verb. And it's often surprising how it can kind of ebb and flow. It's like the moon. We think it's disappeared, and suddenly it shows up again. It's not a permanent state of enthusiasm. I'm thirty-five years in a relationship, and I practice. I have two boys—I practice. It's not just romantic love."

So at the end of the day, every couple needs to have convos that are important to them, be it veganism, kids, money, schedules, residence, (fill in the blank), with ease. Remember, the conversations are not about the relationship; the conversation is the relationship. I'm constantly reminded of this; in fact, I was reminded of it this morning. What gets talked about, and how it gets talked about, determines what will happen — whether a partnership will flourish or fail, regardless of the stage of the relationship.