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Where To Draw The Line In This Friendship?

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I think it all comes down to it being none of my business and I should just stay out of it. However, I am having a hard time doing that. This is a long story as there is a lot of background to it.


A few years ago, I dated this guy for about six months. Being young and foolish, he was also going through a divorce and I know in hindsight it was just not a wise decision on my part. Needless to say, he wasn't ready, it was a rollercoaster and we had a bad falling out. About a month later, after his divorce was final, he met a girl and proposed to her about seven months later.


Well, back in January--3-ish years into their relationship--she called off the wedding. He and I had been in touch now and then during their relationship, because I had forgiven him and moved on. After they broke up, he kind of turned to me for support. I concluded that while he was not a good boyfriend, I did appreciate his friendship and we hang out a couple of times a month. He confided in me the other day that he considers me one of his best friends, which I thought was nice and I was glad we had reached that point over the last few years. Now here is the problem, and where I feel like a horrible, judgmental friend:


I noticed via tumblr and facebook that he and this girl, who is 18 (12 years younger than him and only just about to graduate high school) have been flirting with each other in a not too innocent way. Since he had once told me that he knows he moves too fast with girls (and he really does) and wanted to learn to slow down, I advised him to take plenty of time for himself to get over his ex. I asked him about this girl when I started suspecting something and he said they were only flirting and he appreciated my concern, but her page and his keep consisting of love quotes, poems and conversations between them that are spelling it out blatantly as so much more. I am not an idiot.


I want to be his friend. But I am finding myself unable to deal with the fact that he is dating, or trying to date, a girl so much younger than him when he is not ready--he told me he was not ready for dating only a few days ago and is a self-proclaimed cynic when it comes to love right now, yet he is attempting something with her. He is going to break her heart and I am just kind of having to sit back and watch him do it. I don't know this girl, but I guess I am seeing myself from a few years ago and know him well enough to know that it will happen.


I don't know what advice can be given. I guess it comes down to whether or not I should say something, or perhaps step back as his friend and let him live his life, even though he has a history (there is more I could say) of being destructive when he is down. Sorry for the heavy read.

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I think since you already expressed your concerns, you just have to let him live his life, as hard as that is.


Yeah...I figured as much. Do you think I am worrying for no reason or does this seem like a valid concern? Not that it matters since I need to stay out of it, I just am trying to figure out if I am overreacting. I know without every minute detail it may be hard to gauge, but just judging by what I already wrote. Thanks.

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Yup. You see the train coming. The train IS coming. It is totally going to squish that girl... but really? It's none of your business. It is his business (he knows he is not ready/will squish her). It is her business (she needs to learn from her own mistakes). Trying to get into their business will only make them hate you.


At this point, I think that all you can do is roll your eyes and be thankful that you know better and that he is just a friend. Unfortunately, part of being a friend is watching people make mistakes (you can warn them once and only once) and to simply be there when they fall. Anything else is controlling. You don't want to be that person.


You've voiced your opinion. Your job is done.

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