Hmmmmm...a little bit of 2X4 time, TFC! Brace yourself.

I don’t think that you haven’t brought up your boundaries with him yet is germane to the question of why you aren’t enforcing them, TFC. You knew about the boundary when you were presented with the issue of him being around that “friend." When he brought it up, you had the opportunity to broach the subject of inappropriate friends in a calm non-accusatory discussion. If he disclosed the fact he would be interacting with her, he was effectively asking you whether it would be all right or not and he didn’t get the response you had a great opening to present.

Lady, please watch for opportunities that come at you out of the blue to bring commonsense boundaries up...for both of you. There’s no requirement to lay all the boundaries out on a table in front of him all at one time. Actually, that’s probably counterproductive. POJA him. Heck, you might even be proactive. Ask him what boundaries he thinks he will need in place. You’ll need to phrase it differently, of course, unless he’s read SAA.

Okay, nothing’s been lost except for a few days worth of time that is meaningless when viewed in context. The neat thing about human emotional interaction is the trolley always comes around again. There are always second chances.

How about bringing this subject up in another conversation, saying you fooled yourself when the subject came up before, but you’ve had a lot of time to think about it and you’ve realized it’s not a good thing for either one of you to have a friend who isn’t a friend of the marriage. Pick your time, place, and atmosphere and try to get a POJA with him. Use the example you used in your last post if you want to.

Better yet, if you have an example of a male friend in your life (past or present...based on an actual event or a potential one) who you might should drop (or have already dropped) for the same reason, make that a part of the discussion. (Or use the example of a girlfriend/sister/coworker/whoever whose experience would contribute to what you're trying to get across. Heck, ask your IC for an example.) Something like that would be a very powerful anecdote he could not help but understand.

Homework assignment <grin>: Read or re-read Not "Just Friends" by Shirley P. Glass, Ph.D. That book is a lengthy discussion of inappropriate friends.

Half full observation: Evidently, he's being very open -- tending toward transparency -- because you apparently knew beforehand he would be seeing/talking to her.