We do not have a date set. We got engaged in the end of April, so the open relationship happened before the engagement.
For our arrangement, each of us at this point has slept with one other person. Unfortunately one of the issues in communication I was speaking about was that I only found out he had actually slept with someone else a few days ago.
A little explanation on that. Before we opened up the relationship (officially) there was a woman that we both were spending time with together, and I would spend time with her one on one as well. It was the sort of "flexible monogamy", I suppose, that sometimes comes with a straight male and a bisexual female.
When we had the opening up discussion, I did specifically state that I would be comfortable with him sleeping with her on his own. The issue that arose however is that it happened in February, and I only found out a few days ago. It led to a long discussion and we've definitely solidified a lot of our boundaries and I explained a lot of issues I was having.
A lot of it stems from him not being overly expressive in his affection with me. I explained that I need him to be more affectionate in public AND in private if this is going to work, because I can't feel that other women are getting something I'm not.
I admit that some of it comes from my own very personal issues as well. I am a larger girl and he is a pretty darn attractive guy, so the likelihood of him finding a girl that he finds attractive that is also into him is much higher than my finding someone who I find attractive that also is interested in me. It is difficult for me when he starts expressing interest in someone who isn't my body type, because then it starts a thought process of what if she has everything I have personality-wise AND has a good body to boot. I will never be petite, as I've been overweight since I was four months old. I can get healthier for sure, but I'll never be "skinny".
Also, despite saying he wants to know and be aware of the guys I get involved with, he was not making sure I knew the girls. These last issues arose because of a particular girl that he hadn't slept with, but things were moving in that direction. Luckily we started improving those communication issues while things were moving with that girl, so we were able to stem that particular tide.
The other thing that makes things difficult for me right now is a fundamental difference in the things that each of is looking for in new partners. He is more interested in just trying something (someone) new. For me, I am past the point in my life where I am interested in having sex with random people. I'm much more interested in establishing a FWB arrangement. I need to feel comfortable with new partners. However, he would prefer that I stay away from our established friends group. Which makes things complicated.
During our recent (and ongoing) conversation though, he said that he would try to work through that issue and become more comfortable with my possibly getting involved with friends, and I would work through and try to become more comfortable with him possibly doing things with other women even if I might be in the vicinity.
We've agreed that both of us would be most comfortable if our new partners were already in established relationships themselves, as that presents less of a perceived threat to our own relationship, as those people would understand the meaning of an open relationship better than a random single person might.
I apologize for the length of this, but these are issues that we are currently in the process of working through, so they're a bit fresh in my mind.