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My WW had kept in contact with a old boyfriend throughout our 20 year marriage via facebook, email, text, phone and occasionally in person (along with a group of other men). Turns out she has major boundry issues, go figure I found out in Jan2014 that 4 years ago they had "drunken sex". Long story short she said after that incident along with several others (work and friends of friends) that I had no idea about she "realized how messed up she was" and made changes in herself and committed her self to our marriage. I found this stuff out initially through a facebook post and then TT for several months. We are working on recovery and she sent a NC letter to one individual and showed me all correspondence.She also agreed to show me any other attempts at correspondence from anyone in her past that have violated boundaries including this x boyfriend. She is being transparent and I have access to her phone and other media.She says she felt very guilty for the infidelity with him 4 years ago and kept him at arms length but she did say he would send a text or call a few times a year leading up to my discovery. She never told him or anyone else outright to never contact her again.She said she will show me any text she gets from him when it happens along with her response that will include a NC request.The last time they had contact was x-mass 2013 and she said he just asked via text how she was doing and she responded "really good" and has not heard from him since. My question is this: Should I ask her to send him a no contact letter now or should I let sleeping dogs lay and wait for him to contact her (he will someday) and have her request the NC then?

Part of me wants to give her an opportunity to show she is committed down the road when it happens. Part of me wants her to do it now but I also feel like she will then be initiating contact with him unprovoked. What should I do?

I would say that you jointly send the NC letter. Just nip this right in the bud while it's in front of you. She writes it but you approve it. Put the OM right on notice that there will be NO further contact of any type whatsoever. Just make sure that YOU are not "blamed" for the NC. She should take full responsibility for her bad decisions and cut him out of her life because she is fully committed to you.

What Skan said but I would add. The last thing you want is to be working on R and at some point when you are feeling good he tries to contact her and it all comes crashing down on you all over again. It's best to get all the messy stuff dealt with ASAP.

There is nothing reactive in reconciling; it needs to be proactive. Have her write and send the NC letter now, don't wait.

Thanks to all three of you for your time and advice. I just brought it up to her and we discussed a few things that have been obstructing my/our recovery. She is not the greatest communicator at times but she is working at changing and I could tell by the way things went that she is making efforts to navigate this in a productive way. After just putting my problem on the table she suggested that she can write a NC and we will look at it together before we send it so we can just be done with this part of things. One more step forward. I'll sit back and wait a few days and see what she comes up with. Thanks again to all of you it was a big help