After they left, I did not speak to Jack for several years until he got in contact with me and we met for drinks and became friendly again. At this point he was no longer with his girlfriend. This was around the time Jack set me up with my now-husband, and everything was fine for a while.
The big change in my relationship with Jack happened when he lied about being single so I would help him hook up with a friend of mine. Thinking that he was single, my friend went out on a date with him and they ended up sleeping together. A few days later, he calls me and tells me his plan worked exactly how he wanted it to: that he had, in fact, recently gotten back together with his girlfriend but told me they were still broken up so I would communicate that to my friend and she would sleep with him. On top of this, he told me that Don knew he hadn’t broken up with his girlfriend and didn’t say anything to me. He was actually boasting about this to me. After this incident, I decided that I did not want Jack in my life at all.
This created an 8-year rift with my husband as he still wanted to be friends with Jack, and I didn’t want to ever hear his name again. The times Don has hung out with Jack since the incident have not gone well. I feel like Don has the weaker personality and he picks up Jack’s characteristics, and I can see the influence Jack has on him – drinking to the point of puking everywhere, gambling, and poor decision-making, in general. Jack even tried to hook my husband up with another girl and sent him nude photos of said girl. He has tried to break us up and cause conflict in our relationship. He even said he would try to sleep with our daughter when she turned 18 (who the fuck says that about a baby?!).
For these reasons and many more, I think my husband should give up his relationship completely with Jack and should not communicate with him at all. I feel betrayed by my husband when I eventually find out he has been communicating with Jack. He says he understands my feelings, but then he continues to secretly communicate and/or get together with Jack, and I find out and we have the same argument over and over. This is basically the only thing we argue over.
So, Dear Wendy, am I being too controlling or am I justified in my desire for Jack to not be part of our life in any way, shape, or form? — Not a Jack Fan
This has been going on for eight years? Then, it’s not likely to change. Whether you understand it or not, Don gets something out of his friendship with Jack that he doesn’t get elsewhere. Maybe in his communication with Jack and, I’m assuming, the limited in-person interactions they have, he enjoys nostalgia for his college days. Maybe he feels young again for a few hours. Maybe he simply appreciates getting a peek into a completely different life. Maybe it renews his gratitude for the life he pursued — the more stable one, with a wife and kid and moral responsibilities. And maybe, for all the bad Jack has clearly exhibited, underneath it all, there are some redeeming qualities that Don still enjoys. After all, you were once Jack’s friend; you must have seen something in him that you liked. Whatever it was that once drew you to him is likely what draws Don to him, and the things that have turned you off have not been as big a turn-off for Don to cut ties with his friend. Obviously.
You say Jack has a negative influence on Don, to the point that Don drinks ’til he pukes, and gambles, and makes bad decisions. How often is this happening? Once or twice a year? If so, I’d let it go. Tell Don he’s free to hang out with his friend, but if he ever drives while drunk or gambles away a lot of money or gets himself into “trouble” (however you define that, and you should be clear with Don about what that means to you), he will have to answer to you. But if he’s out with Jack on a more frequent basis and Jack’s influence is truly affecting your life — in more than your simply being annoyed by Don’s questionable choice in friends and what you perceive as his lack of loyalty to you — then you have justification to ask, and even demand, that he stop communication with Jack or there will be consequences. And if he doesn’t — or you can’t trust that he has — the consequences of that should include marriage counseling to work through this rift, find common ground, and address the issues this friendship has created in your relationship.
Finally, if Don decides to continue his friendship with Jack in limited fashion (in-person hang-outs once or twice a year), you have every right to demand that you and your daughter never be exposed to him. Your daughter should never know Jack personally,and, if she knows about him at all, you can tell her he’s a friend of her father’s who is not a friend of yours because he doesn’t respect you or women in general. If she asks why her father would be friends with a man like that, you’ll have to tell her to have her dad explain that one.
If you have a relationship/dating question I can help answer, you can send me your letters at firstname.lastname@example.org.