Yeah, John and I get along ok. Like I said, they've been involved in our lives for a while now, so I've already been around him enough to like him. He actually came over for Christmas dinner because Jane was out of town visiting family, which was weird, but not uncomfortable. Wifey & Jane have been trying to get us to hang out and be friends for like a year, but our schedules have never really matched up well.
He seems perfectly fine with whatever Jane wants to do. They have fairly separated lives, and their own other partners, and make a big deal about their autonomy, which I suppose is what works for them, so I don't think he's "allowed" to give much of an opinion on the matter. I know Jane doesn't tell him what she thinks of his other partners (they make a big deal about their communication skills, too, which I find amusing at times). I think he's urged caution because of the risk factors, and been otherwise supportive.
I have encouraged Wifey to proceed at times when she's considered retracting her offer of intimacy because communication with Jane has been difficult. We're both scared. I work on communicating with Wifey a lot about all this, and we've talked about what we're each ok with . . . Wifey just wants to kiss and hold hands at this point, and doesn't know if she'll ever want more than that. I've actually initiated discussion with Wifey about how I'd feel about various possible levels of intimacy between them, and I still have lines I'm not comfortable with them crossing.
What are appropriate levels of involvement? Assuming this thing with Jane becomes a relationship, how much can I ask Wifey about it? Jane and John seem to have a "hands off" policy where they don't really talk about it except as it impacts each other (scheduling), but I'm not sure that's healthy either. Do I have any right to be uncomfortable about what Wifey & Jane may do together? Again, remember, decade of monogamy starting from zero sexual experience.
I worry that I'm making myself too involved in this, but I know that if I don't keep pace with it, insist on talking with them both about it from time to time, maybe frequently with Wifey, I'll start to worry, or fear, or feel lonely and disconnected from this beautiful new experience Wifey is getting to have. I need to feel connected to or a part of her sexual experiences in at least a small way, and though I've been a part of this process so far, I know I won't be later on, and I'm not sure yet how to feel about that. If I feel too disconnected from this part of her life, I worry that I might start to feel disconnected from her, or get jealous or resentful. I'm already envious, just of their level of friendship. I miss having friendships of my own (I haven't had those in a while, as we're still working to recover from some heinous financial shit, my best friend of 20 years died a couple years ago, and we've only been in our new town for three years), I miss spending time with (non-Wifey) individuals who make me happy just by their presence, who care about me and worry for me. And yes, I'm envious of the rest (whatever that is, whatever that grows into becoming), too. It sounds absolutely delightful for them, nervousness aside, if they proceed.