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How do you know when you're ready to try friendship again?

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Bit of backstory: I dated a person who I'd been friends with for over five years prior to us dating. He broke it off because he "wasn't feeling it" -- a good reason. We hadn't been dating all that long or all that seriously... but I was falling in love. He wasn't a jerk about the breakup, he was honest. He said very clearly that he wanted to preserve the chance for a friendship in the future, and I explained that I needed time to myself before I would be able to be a friend again. We've been split up for almost two months now.


Since the split he has initiated communication through electronic means several times, usually with some kind of reason/excuse to talk to me... then when I respond to what he sent he mentions that he's missed me. I know he's going through a very tough time right now outside of romantic entanglements. I have felt badly that I had to take this time to heal, because I can't be there for him (and he's been there for me through a *lot* of crap). But I know it was unavoidable and necessary.


Where I'm at right now:


I know the breakup was for the best and that even attempting to get back together would be a Very Bad Idea.

While he's in no way a bad person, there were compatibility issues that I had been willing to overlook before... but now I see them much more clearly.

He's had extremely limited relationship experience, and more than a few things about the way this went down remind me of the relationship with my high school sweetheart -- he and I were on-again, off-again for many years and I sense a lot of the same type of dithering here. I need someone who got that crap out of their system a long time ago... who knows their heart and knows what they want.

I don't think about him daily, or even every other day -- only when my coworker who is his friend mentions him, for instance, or when I see comments he's made on FB... and of course, when he's contacted me.

Hearing his name isn't painful -- I don't feel the urge to cry or get angry when I do think about him,. I still feel a little sad and regretful.

I know his "I miss you" is him missing friendship and companionship, not the relationship.

I haven't had to fight the urge to contact him in well over three weeks -- he wasn't the person who came to mind first when I wanted to share good news with someone (getting hired on full time at my job and getting a raise at the same time) this week.

I know that even if we do re-establish a friendship, it will never be the same as it was.


For those who actually want to or have successfully re-established a friendship with an ex, what made you decide you were ready to make the attempt?

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I needed time to myself before I would be able to be a friend again. We've been split up for almost two months now.


I know the breakup was for the best and that even attempting to get back together would be a Very Bad Idea.

While he's in no way a bad person, there were compatibility issues that I had been willing to overlook before... but now I see them much more clearly.

Wow...I am in a similar situation, except that I am missing him a lot...as we work together, it will be after 2 months that I will now be able to see him(he is on an out-of-state assignment).

I also feel that u need the time to completely get out of this, but yea, the friendship will never be the same. Everytime you are together, you will have a little bit of that relationship feeling. At least I will have that...I am still thinking that how should I react once I see hime after two months, as the breakup took place just before he left

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Sorry, I am going to respond before reading your post, then go back and read it and see if my answer changes.


You know you are ready to be friends when you no longer care enough to ask if its too soon to be friends.


Ok after reading it my answer still hasnt changed. Just the fact that you are thinking over this as much as you are tells me you probably arent ready. If you are truly over the relationship aspect of it all, then just let it happen naturally. Either he will contact you and you can reciprocate or you will find yourself at some point in the future wanting to contact him for whatever reason without all these thoughts running through your head as to whether you should or shouldnt.

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You are ready to be friends with an ex at the stage where friends happens NATURALLY, and you happen to cross paths with ZERO expectations or hope to be with them, not because you feel like you need to seek each other out. And only if you wouldn't feel the slightest ounce of disappointment or hurt if they were dating someone new, and you could genuinely be happy for them. But why dig up a "friend" that has all of this baggage attached when there are many new friends out there waiting to be made where you don't have all that history?

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I read this post and then thought it over.  You are not ready to be friends, and I don't think he is either.Let me explain.


You claim that he was not feeling it while you were falling for him. While it wasn't that long, he probably a- found something that was easier or b- saw you as not pulling your weight c- got scared of his down feelings. He wanted to keep you around without getting into a relationship with someone he cares about.


Now you are analyzing and wondering what is going on. Was it because of your past or something else? Does he miss you because of the friendship or something else?


So you can do a few things. One... is Nc/Avoid which is not helping you heal. Two... is being in contact with him on a minimum level to be there IF you wish. Let him contact you but choose it wisely. You may find yourself wondering why he is in contact with you... is it because he is addicted/attached or he may actually have genuine feelings for you. Either way, this man you have feelings for will not be your friend for a while.... and don't see this as false hope but I do not believe that he is being genuine with his feelings with you as well. Play this out right and you will see what his true intentions are if you so desire.


Or you could just go full NC, pretend not to care and then months don't the road see him with some girl... and that won't bother you right? Point is, you're not ready if you are asking.

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To be fair the length of the post and the amount of overthought put into it is a prime indication you shouldn't be friends.


Typically you are friends when you run into eachother and go "hey how you been, ah yeah what are you up too these days?"

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I am friends with my Ex's but it only happened after a long period of NC.


My first boyfriend who I was with for 7 years..we were NC for about 8 months afterwhich we have suddenly become friends due to a whole network of mutual friends. I was the one who reached out to him through text greeting him a happy birthday. After that, we would communicate every once in a while but not in a manner to hang out or have a serious conversation.


The 2nd EX and I were together for about 8 months but have worked with him for a year prior to that..we were NC for 2 years. We are now very good friends confiding to each other, but for some reason the magic is just gone. Which makes it all the better because there are no more side thoughts of what if's and misconstruing kindness to him liking me.


From the sound of your email, I would say give yourself a little bit more time until all the negative feelings are gone. Forgive and try to move on, but believe me it is easier said than done. Do not focus on what might have been's because all the more you do that, the more deeper the regret becomes. Most of all, listen to everyone else here - NC and heal.

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Just remember that, because you want to be friends doesn't mean your ex does. I recently tried to be civil and such with my ex after a drunken mistake but things went downhill fast. If your ex cant let go of resentment breaking NC would be a waste of time.


I honestly believe exes can be friends after awhile and in the rare case they work out to be close friends but I'd rather let go and cut my loses than the potential fallout from breaking NC.

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