I've been poly my entire adult life, though stumbled through it for a long while without much idea of what I was doing and developed some healthy relationships over the years (along with quite a few very messy awful ones during the first ten years) through sheer luck before really begining to develop good skills. I did messy nonmonogamy as a teen with one brief try at monogamy that made it very clear it wasn't for me, and then as an adult have only engaged in relationships where I was clear I was poly from the getgo. I practiced poly in ways that weren't in tune with my values when I was younger because a lot of the reading I found at the time emphasized rule based hierarchy, and while I grew away from that over the years and did some reading about RA, I have only in recent years really delved back into actually looking at where the poly literature has gotten to in the past decade or two.

I have three relationships, of 15 years, 13 years and 6 years in length and they've coexisted without any large poly related conflict for that time, so I haven't really come into situations that forced me to do a lot of growth in that way. My partner of 15 years, we'll call it Cypress, is pretty poly saturated at one, and my partner of 13 years, we'll call them Oak, has other partners and has managed their own relationships in a pretty relaxed and carefree way that's not really led us to introspect much about how we do things. Our particular dynamic is not super enmeshed, and doesn't really have any structure outside of discussing new risks before sex when we see each other.

That brings me to my partner of 6 years, I'll call him Briar. Briar had not had any experience with poly before me, or really much of any relationship experience at all. We took our relationship slowly, I was hesitant dating someone without poly experience, but we had a very strong connection from the start and it felt worth trying. Three years into our relationship we went from long distance to living in the same city and sharing space between our homes frequently. A year later we moved with a group we were building an intentional community with to community land, and have been living together the last two year in our community. Cypress also lives with us and has lived with me for 14 years, though in a pretty unenmeshed way. Briar and I are very enmeshed, we spend a majority of our time together, sleep together about half of the week, and while we don't share finances, kids, or are legally married, those are all on the table for the future.

Recently Briar has been interested in pursuing other relationships, previously he's had a few crushes but with incompatibilities there that prevented pursuing them from even being an option, so this is the first real time he's felt other relationships were something he actively wanted to start. We've been having a lot of conversations around this because despite having been in a poly dynamics for the last 6 years, he feels like he doesn't really have an understanding of how to go about actually having multiple relationships. The way mine work aren't a great blueprint for that. Cypress is incredibly independent and doesn't really have any strong relational needs or expectations, it gets along with just about everyone and it and Briar adore each other, but it relates to others almost like a cat in that it doesn't mind folk existing in its space but is equally comfortable just being alone and not interacting for days. Oak is more a comet dynamic for me, we see each other a few times a year, and we don't really have any structure in our relationship, the relationship has adapted over time through periods of living together or not, talking often or talking rarely, etc, with both of us pretty much just riding through whatever evolves at that time.

What Briar is looking for is more how to balance actively dating and getting close to and developing more intention based relationships with other people while also nurturing our current pretty enmeshed relationship, and I've honestly not had to practice those kind of skills in a long time. He wants to do the kind of work that folks usually do when first opening up to kind of learn poly from the ground up, and I'm excited and enthusiastic to do that with him because this has highlighted a lot of missing skills on my part as well because it's been a very long time since I've been in a relationship that created any real challenges or conflicts or new big things. We've begun reading Polysecure and listening to some podcasts, I've also read some other articles like the most often missed step, and have shared those with him to read when he has time.

I think the question I'm coming to upon this journey is, when do you know you're done doing the work and ready to dive in to other dynamics? Obviously we're already poly, there is nothing holding him back aside from feeling like he needs more knowledge before he's comfortable moving forward. I guess what are the basics you would want to know and have thought through and read and discussed in this kind of situation? It's a huge lack of oversight clearly that we didn't do this work early on, but I don't know that he was thinking through the possibility of dating other people because his life was already pretty busy, and I kinda stopped at the point where we'd talked through what kind of relationship I could offer and what my other dynamics were like, and a bit of my philosophies around why I was drawn to poly and RA. I think he's a bit caught between wanting to read and learn and process all he can first but not knowing when you have done that enough to move forward, and wanting to just learn by doing but not wanting to involve another person and their emotions in that while potentially stumbling into a lot of pitfalls. So any advice on how to know when you know enough? And also any pointers on key things to read or listen to beforehand as part of this process for him and for us?