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I'm a guy, 32, and I've known this girl for four years. I consider her my best friend. She'd been in a relationship the entire time I've known her, and I've never been "pining away" or hoping for an opportunity some day. I've just been enjoying our friendship, and in fact, over the last couple years, I had become buddies with the guy she was with. But, their relationship recently ended, and he has moved away out of state. And that's gotten me thinking, and I've realized that I actually really like this girl, and would like to potentially explore more.

 

But, I understand situations like this probably don't tend to actually work out, right? Obviously, if I pursued it at all, I'd want to give her sufficient time to move on. I just wonder if, given the situation, there's any way I could ever approach it without ruining the friendship? I don't want to lose her, and I don't want her to have the wrong idea and think I've had ulterior motives all along. Part of me feels terrible for having these feelings, and for "betraying her ex". But at the same time, I'm not so sure I can easily make them go away, and I'm worried that me always carrying a torch for her in the future will negatively affect the friendship, as well.

 

I just don't feel like I know what the right thing to do is, here. I don't want to lose what I have with her, but I don't want to spend the rest of our lives wondering what if.

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It has nothing to do with her being a friend, but that she just got out of a LTR. She is nowhere ready to date someone. You will only be a rebound.

 

How long were you going to wait before approaching this? When did she break up?

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I'm not sure why any man would put up with a woman who has a male friend who considers her his best friend. It's not a surprise to me that her relationship just ended. If you think this the type of woman you want in your life, I think you're already making the wrong move. She doesn't appear like she has a good head on her shoulders or knows how to create or stick to boundaries in a relationship.

 

I think your fear of "losing her" also comes from the fact that you've seen another man "lose her" and you're aware of your own intentions the entire time you've known her while she was in a relationship with someone else. Insecurities breed more insecurities. I'm sorry but I don't think this was good from the start. There's too much duplicity and selfishness, lack of boundaries and you are in danger of being a rebound.

 

The right thing to do, if you were thinking of the right thing at the start, would have been to distance yourself when you felt yourself develop more romantic feelings for her early on. You're in a sinking ship so if you feel you want to ask her out and can't help yourself, I don't think you can do any worse other than fear rejection. This would be your ego speaking. You'll get over it though. It was wrong from the start.

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Has she ever shown you any signs that she might have feelings beyond friendship for you? If not, if you really value this friendship, and if you care enough for this person, then don't do anything at all. She would certainly make it obvious, in some way, if she desired anything more than friendship from you.

 

Be thankful for the great friendship. Acting upon the "what if" could very easily destroy what you have with her. Just let your friendship continue to play out, and if anything comes of it, naturally, in the future, great. If not, that should be geat too, a close friend for life. You can't put a price on really good, close friends imo.

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How long were you going to wait before approaching this? When did she break up?

 

I don't really have a "plan" for approaching it. I'm mostly just trying to process these things, and figure it out, because I know it will probably be months, at minimum, before she is actually ready to move on. The break up happened less than a month ago. Like I said, I have no intent of immediately springing anything on her. I'm just trying to figure out now what makes the most sense for the future.

 

I'm not sure why any man would put up with a woman who has a male friend who considers her his best friend. It's not a surprise to me that her relationship just ended. If you think this the type of woman you want in your life, I think you're already making the wrong move. She doesn't appear like she has a good head on her shoulders or knows how to create or stick to boundaries in a relationship.

 

I mean, I understand why you see it that way, but the truth is, she's not THAT kind of person. She's not disloyal, she's not a cheater, she's not someone who strings guys along. And he was never the jealous or controlling type. Besides, I didn't have any malicious intent of undermining their relationship. She and I were good friends, he was okay with it, and he and I connected later on, too.

 

The thing is, I don't know, maybe subconsciously, there was a part of me deep down that was already attracted. But that was never something I really actually thought about these last few years. We've all been friends, and I've been totally happy with that. I never expected their situation to change. When it did change, it shocked me, and it made me start thinking about a lot of things differently.

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Has she ever shown you any signs that she might have feelings beyond friendship for you? If not, if you really value this friendship, and if you care enough for this person, then don't do anything at all. She would certainly make it obvious, in some way, if she desired anything more than friendship from you.

 

Be thankful for the great friendship. Acting upon the "what if" could very easily destroy what you have with her. Just let your friendship continue to play out, and if anything comes of it, naturally, in the future, great. If not, that should be geat too, a close friend for life. You can't put a price on really good, close friends imo.

 

I'm not sure. I mean, I'm not very perceptive of "signals" in general, so I wouldn't even know what to look for. I also don't necessarily feel like she would've been "giving me signals" while she was in a relationship. She's not a disloyal person.

 

Certainly, the plan for now is to just stay the course and play it by ear. I just don't know that my feelings will fade as easily as I'd hope that they would, and I'm worried that will also lead to problems later on.

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No one can say for sure what will happen or what she is or has been thinking.

 

This isn't a movie where one day you are eating pizza hanging out and look into each others eyes and just fall into a deep romantic kiss.

 

Chances are she will eventually meet a new guy and get into a serious relationship and possibly get married and your friendship will change to an acquaintance or it will just fade away. Most guys will not be cool with a guy that has feelings their gf hanging around as a bestie. So that means you will be on the outs either way so you might as well take a swing at it.

 

Give her some time to heal and after a while ask her when she thinks she will try dating again. She may ask you why you want to know so you better have an answer ready.

 

Be a friend and when the time comes be brave and talk to her about how you feel. It won't kill you if she isn't interested in a relationship with you and if the friendship ends it ends which is probably best because things have changed and cannot go back to the way they were.

 

In the meantime you need to figure out exactly why your feelings changed. What has been going on in your life? What has changed after all these years where she is someone you want to be with romantically?

 

Make sure you know yourself BEFORE you do anything.

 

Lost

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I don't really have a "plan" for approaching it. I'm mostly just trying to process these things, and figure it out, because I know it will probably be months, at minimum, before she is actually ready to move on. The break up happened less than a month ago. Like I said, I have no intent of immediately springing anything on her. I'm just trying to figure out now what makes the most sense for the future.

 

 

 

I mean, I understand why you see it that way, but the truth is, she's not THAT kind of person. She's not disloyal, she's not a cheater, she's not someone who strings guys along. And he was never the jealous or controlling type. Besides, I didn't have any malicious intent of undermining their relationship. She and I were good friends, he was okay with it, and he and I connected later on, too.

 

The thing is, I don't know, maybe subconsciously, there was a part of me deep down that was already attracted. But that was never something I really actually thought about these last few years. We've all been friends, and I've been totally happy with that. I never expected their situation to change. When it did change, it shocked me, and it made me start thinking about a lot of things differently.

 

She was with this guy for 4 years, I think you are looking at about a year before she has processed things. I could be wrong.

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My advice is to leave it alone for now and let the dust settle. If the both of you should grow closer, it'll happen organically. If she wants to kindle a romance with you now so soon after her break up, you should remain cautious and don't jump into anything with her. You don't really know someone in a relationship unless you're dating them so there are aspects about her you just don't know about yet. I think the worst disservice we often do to ourselves in dating is assuming that we know someone before we actually do.

 

Keep a cool head and remain a good friend - nothing else at this time.

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Yeah. Like I said, I have no intention of ever trying to approach it if she's not had time to properly move on. It's not that I'm wanting to act right now. I'm just trying to figure all of this out in the meantime, because I didn't expect to find myself feeling this way.

 

And I'm worried about how this will affect the future. I'm worried I'm going to feel bad when she starts dating and ends up with someone else. I'm worried that, try as I might to contain it, I'll skip and say something stupid.

 

I do worry about the fact that it's probably unlikely she'll be able to find another guy that's cool with her having a guy friend. But, she seems to have an attachment to me and I also don't get the sense she'd so easily drop me. Not that I'd want her to ever be in the position of having to make that choice because of me.

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I have had a ton of male friends, and we both have zero interests in each other sexually. I have only ever once dated a friend, once. And we're married with two kids and two dogs and a house and are happily married even with bumps along the way.

 

Life is too short. If you think she's vibing, then ask her on a real date. Like with activities (boating, hiking, zoo, museum (if open), anything different from hanging around your pads) and dinner and flowers. You've been friends, so if you want to get out of the zone, you must romance!

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Without over complicating things or ruining the friendship, I'd say at some point down the road, if the moment feels right, simply ask her if she had ever considered you and her in a romantic way or would she ever consider that. See what she says. Don't pour out any kind of feelings, confessions, etc. Just a simple question and the answer will tell you what you want to know without risking your friendship if that answer happens to be no. Keep it very light like that and it won't create awkwardness or tensions.

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Regardless of the fact you don't want things to change, you're being unrealistic. Even with same sex friendships, there's a possibility they will change whether for better or worse because of personal changes and priorities. Male/female close friendships have different dynamics--very different, and at a higher risk of fading or ending. I know I'd never have dated my now husband if he'd said he had a female best friend. It's just something I'm not comfortable with. There's a smaller pool of people out there okay with this, so the both of you would have to find partners fine with this, so what's the possibility of that happening?

 

And basically, how will you bond with a new gf when you're pouring your emotional time and energy into a female best friend you hoped for more from? It also raises ethical questions. If a new dating prospect asks, "Do you have a crush on your bestie?" What will you say?

 

Have I known people who were friends, dated others, and then eventually married each other? Yes, I knew of one couple who did and had a son, four at the time I knew them, so their relationship had been successful for quite a while. I lost touch because it was just a co-worker.

 

My suggestion? Don't think of her as your best friend, because labeling something like that that's bound to not last will psychologically upset you even more when it wanes. Sure, still be friends but expand your world and hang out with other guy friends more often. When enough time has passed, yes, I'd have a conversation with her, saying that you two get along so well, that you've been wondering if you two should give dating a go. She will give you the feedback you need. If it's a no, sure, it will be awkward for a while but it will pass. But again, if it's a no, you're going to have to stop spending so much time with her and begin to think of her as just one of the guys. If she questions why you're distancing yourself, be honest and let her know that going on as you have been, being besties and spending tons of time together, is not going to be conducive to you being able to get attached to a romantic partner. If she truly cares, she will take your best interest to heart and comply. If she only cares about an ego boost and her own needs, she will ignore your wishes, and you'll have to be stronger and move on, setting your boundaries. Good luck and keep us updated!

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Without over complicating things or ruining the friendship, I'd say at some point down the road, if the moment feels right, simply ask her if she had ever considered you and her in a romantic way or would she ever consider that. See what she says. Don't pour out any kind of feelings, confessions, etc. Just a simple question and the answer will tell you what you want to know without risking your friendship if that answer happens to be no. Keep it very light like that and it won't create awkwardness or tensions.

 

^ I think this is great advice!

 

If you want to know, just ask her and be simple about it. I wouldn't wait too long. Not everyone needs tons of "recovery time" after a break up. I think there are times when people may have emotionally been out of their previous relationship for a while. But everyone is different, there's no right or wrong. But IMO, if you wait too long she may have another bf.

 

I see no reason you can't ask her soon and casually. If the answer is no, then you don't have to worry about a time frame. If the answer is yes then she will have it in mind for whenever she is ready to date- be it a month or more.

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^ I think this is great advice!

 

If you want to know, just ask her and be simple about it. I wouldn't wait too long. Not everyone needs tons of "recovery time" after a break up. I think there are times when people may have emotionally been out of their previous relationship for a while. But everyone is different, there's no right or wrong. But IMO, if you wait too long she may have another bf.

 

I see no reason you can't ask her soon and casually. If the answer is no, then you don't have to worry about a time frame. If the answer is yes then she will have it in mind for whenever she is ready to date- be it a month or more.

 

Yeah, as far as time goes, that's something I wonder about, because I kinda get the sense she's been unhappy for a while now. Around this time last year, they were having some problems, and she had told me then she was thinking about ending things with him. But then they seemed fine after and she never told me anything more about their relationship issues or anything, so I just assumed they'd worked everything out.

 

She has been kinda distant with me this whole last year, and it feels like this last year has been more of me hanging with him than with her. But, now that he's gone, she seems excited to get back on track with me, and she seems upbeat just from the texts we've occasionally been exchanging. I haven't actually seen her in a little over a month, so we've not actually talked, but she's either pretty happy or she's putting on that face for me, though I don't know why she would, as she's always been pretty transparent about how she's feeling.

 

Either way, if there's an opportunity, I certainly don't want to miss it, but I also don't want to "pounce", and I wouldn't want to come at her about it if she's not actually there yet. At the same time, I'm pretty sure she doesn't want to waste too much time in life, as she seems to really want marriage and kids in the next few years. So, I really don't know what her time frame will end up being for recovery.

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Nice guys don't pounce, but they also don't get the girl (I mean, don't wait - the longer you do, the more you overthink. The more you overthink, the most anxious you get. The more anxious you get, the more you don't do anything about it). I would take her out to a meal, and ask her point blank, "why is it that we've never dated?" Let her answer. If she says, "well, I don't know," or "you never seemed interested," then ask her out then and there. Now if she says, "because we make better friends," then jump ship & bail on asking her out. But if the that last time, makes you heart feel super deflated, I think you need time to decompress on how you feel, because you deserve someone who wants you back.

 

And if she says, "I never thought of you that way before" then you can say, "how about now?"

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Nice guys don't pounce, but they also don't get the girl (I mean, don't wait - the longer you do, the more you overthink. The more you overthink, the most anxious you get. The more anxious you get, the more you don't do anything about it). I would take her out to a meal, and ask her point blank, "why is it that we've never dated?" Let her answer. If she says, "well, I don't know," or "you never seemed interested," then ask her out then and there. Now if she says, "because we make better friends," then jump ship & bail on asking her out. But if the that last time, makes you heart feel super deflated, I think you need time to decompress on how you feel, because you deserve someone who wants you back.

 

And if she says, "I never thought of you that way before" then you can say, "how about now?"

 

Heh, sure. Though the reason we never dated is because she's always been with her ex since I met her. In any case, I guess there are low pressure ways to float the idea, so if I ever feel so inclined, hopefully I can use one of those instead of fumbling into something stupid.

 

The timing is still going to be tricky to me. I don't know how I'll ever know when it's appropriate.

 

The other thing I still think about is, well, her ex. I wonder if my friendly relationship with him will make her feel less inclined to consider me. Granted, he's out of state now. Still, there's a part of me that feels guilty, especially because before he left, he told me I was the first "new" friend he had made in the last several years. He expressed an interest in staying in touch, and I was open to it. I haven't really heard anything from him since the last time I actually saw him a few weeks ago before he moved, though. We're still all friends on social media, though. I dunno. It's like... I'd feel bad trying to get with "his" girl, but at the same time, he's not in the picture anymore, and if she and I were both interested, I don't necessarily think we should hold back just because of what her ex might think. But then, I wonder if that's just me looking for justification for being a bad person. Sigh. I dunno.

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The situation can work. I was the one interested in someone else only to have my heart broken. She was the good friend who supported me through it all who had feelings for me. She let me work through my feelings first, just being a great friend. And one day I realized my feelings for her. And it happened a lot quicker then you would think.

 

I think you are handling things well. Be a friend to her and just enjoy being around each other and doing things together. You don't need a plan, trust your gut. When the moment is right, you'll feel it. When you tell her, be honest. Just don't wait to long.

 

I also wouldn't feel bad about the ex. You can't control who you are attracted to, and you are not doing it to intentionally hurt him. If they are not together, you should be able to pursue what will make you happy. And he can be sure that you will treat her well.

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The situation can work. I was the one interested in someone else only to have my heart broken. She was the good friend who supported me through it all who had feelings for me. She let me work through my feelings first, just being a great friend. And one day I realized my feelings for her. And it happened a lot quicker then you would think.

 

I think you are handling things well. Be a friend to her and just enjoy being around each other and doing things together. You don't need a plan, trust your gut. When the moment is right, you'll feel it. When you tell her, be honest. Just don't wait to long.

 

I also wouldn't feel bad about the ex. You can't control who you are attracted to, and you are not doing it to intentionally hurt him. If they are not together, you should be able to pursue what will make you happy. And he can be sure that you will treat her well.

 

Yeah? I mean, what counts as "waiting too long"? I really have no idea what a reasonable amount of time for her to move on and be open to new possibilities would look like.

 

Sorry to hear that. It doesn't seem like buzzing around in the friend zone is going to help.

 

In fact the more you do this the more it places you into a platonic place. You've become a male-girlfreind .

 

What actually constitutes a "friend zone", though? I've always felt like there was maybe enough "distance" between us that it's not typically felt like I'm a "male girlfriend", but I really don't know, as I'm not familiar with what that dynamic is usually like, and how not to be that.

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Wish I could you a specific time for "too long" but it varies. Some people talk a long time to get over someone. Some people can move on quickly. Like most relationship things, it kind of all depends on the people involved. My philosophy is to just go with your heart. When you feel it's right, go for it. There's never a perfect time and it's a risk whenever you say it. You know her best, so you'll know it. When you can't hold it back anymore, when you see her smiling in a certain way .... tell her.

 

I'll probably be different then most advice you'll hear, so feel free to do what you think works best for you. I've never bought into the "friend zone." I think it's more a justification guys (and some girls) use to explain that there simply wasn't that level of mutual attraction or that the timing wasn't right, etc. It's not like your boxed into this corner where you can never escape from. Friends can become more, and relationships can end and become good friends. In fact, the foundation of a good relationship is a solid friendship. If things don't work out, it won't be because you were too much of a friend and that caused you to be stuck from becoming more. It's just that it was not meant to be. Which would suck, I know. But it won't be something to beat yourself up over.

 

Bottom line, just be you. She already likes who you are. Don't overthink it. Just go for what you want.

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I actually disagree that because she had a male best friend that she's dodgy or trying to cheat or whatever. I think men and women can actually just be friends if they don't have feelings for each other. One of my best friends is actually male and there was nothing actually there, just friendship. However my best male friend is bisexual but mainly only into guys. That may have something to do with it. It is possible for people to have opposite gender friends though and it doesn't make it sleazy. I actually think it's nice to have opposite gender friends because you can get a different perspective on life from a different gender.

 

The good news OP is that being your best friend, you obviously do have a very strong connection with this girl. However it's hard to know whether she did so well just being friends with you because she friend zoned you and only sees you as that. How long has she been single? Personally I'd go for it but only if she's had at least a couple of months to move on. I mean she was in a four year relationship. She's not going to be over it overnight, she needs time. But clearly you do like this girl for real and it's not just infatuation because you know her really well. You are really close to her and obviously truly like her for who she is and this is the real deal for you. I would say give her enough time and then tell her how you feel. She might reject you but if you never try you will definitely fail at getting her. If you try at least you have some chance.

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I'll probably be different then most advice you'll hear, so feel free to do what you think works best for you. I've never bought into the "friend zone." I think it's more a justification guys (and some girls) use to explain that there simply wasn't that level of mutual attraction or that the timing wasn't right, etc. It's not like your boxed into this corner where you can never escape from. Friends can become more, and relationships can end and become good friends. In fact, the foundation of a good relationship is a solid friendship. If things don't work out, it won't be because you were too much of a friend and that caused you to be stuck from becoming more. It's just that it was not meant to be. Which would suck, I know. But it won't be something to beat yourself up over.

 

Yeah, I've never fully bought into the idea of a "friend zone", but I also understand it can be difficult to change how you view someone. Especially in this situation, she's viewed me as a friend for so long, she saw me develop a friendly relationship with her ex... I'm not sure whether she'll be able to reconcile that, you know?

 

More than rejection, the thing I fear the most is how much this might jeopardize our friendship if her answer is no. I mean, I can do my best to approach it in the least "pressure-y" way possible, but if she sees me so much as "just a friend", it might be so jarring for her no matter what that she can't continue being friends. I'm also very concerned that me trying to have this discussion at all will raise a lot of questions. I don't want her to think our entire friendship was a lie all these years and that I was just waiting around hoping her relationship would fail so that I could try to get in her pants. I don't want her to feel like I ever had ulterior motives for being her friend. But that seems like a tricky thing to dodge, here. I dunno.

 

The good news OP is that being your best friend, you obviously do have a very strong connection with this girl. However it's hard to know whether she did so well just being friends with you because she friend zoned you and only sees you as that. How long has she been single? Personally I'd go for it but only if she's had at least a couple of months to move on. I mean she was in a four year relationship. She's not going to be over it overnight, she needs time. But clearly you do like this girl for real and it's not just infatuation because you know her really well. You are really close to her and obviously truly like her for who she is and this is the real deal for you. I would say give her enough time and then tell her how you feel. She might reject you but if you never try you will definitely fail at getting her. If you try at least you have some chance.

 

Yeah, the break up is only a few weeks old right now (and actually, he only finished moving out of her place and moving out of state a week ago). So, I wouldn't pursue anything until she seemed to be in a good place. It just feels hard to read. If she's been unhappy for a while, then maybe she'll be ready to move on sooner. If her "biological clock" is driving her, she might not want to waste too much time mourning a relationship that went nowhere. I don't know the answer to these things, and I don't necessarily know how to discern said things from her. I mean, she seems upbeat and cheerful in our little text chats, and she seems excited to see me next week for the first time in over a month, but I don't know if she's just putting on a happy face, or if she's genuinely feeling like a weight has been lifted off her shoulders. I dunno. And I'd hate to miss that window of opportunity.

 

What are your thoughts on the relation between me, her, and her ex? I wonder how willing she'd be to reconcile the idea of considering me as an option, knowing that I had a friendly relationship with him for the last couple of years. I mean, he's out of the picture for both of us now, but we're all still friends on social media and stuff, and there's a very loose sense of being "in touch" in a "we still occasionally react to memes from each other on Facebook" kind of way. I don't know that we'll remain in touch beyond that sort of thing, but still.

 

I still haven't figured out if pursuing her will ever be "okay", given the friendship I had with both of them, even though I considered her more my friend than him.

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Sonic, you're dealing with the same problem friends everywhere have dealt with. And sadly, there are no easy answers. Every person reacts differently. Only thing I know for sure is that nothing happens unless you try. So you have to decide if the risk is worth the potential reward. Yes, plenty could go wrong. Plenty could also go right. If you don't try, you keep the friendship, but you'll never know what would have happened. And in my experience, the never knowing is the worse part.

 

That you're worried about all these things shows that you're a good guy at heat. No matter how she feels about you romantically, I'm sure she sees that you are a good guy and won't think anything negative or that you were trying to get close to her all this time.

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Yeah. I dunno, I just wish I could read her better so that I could more easily figure out whether or not I'd be making a horrible mistake to take the chance. I know she has some kind of "attachment" to me, but I just can't figure out to what extent that attachment is.

 

In any case, something I've been realizing now, too, is that it's probably going to be a while before she's had enough time to move on. And while I'm doing my best not to dwell on my current struggle, it's very difficult to get it out of my mind. I've been trying hard to distract myself with work and hobbies, and whatnot, but it's hard to get it out of my mind.

 

And because it'll probably take, I dunno, 6 months, 8 months, a year, who knows, for her to move on, that's a long time to be stewing over these thoughts and feelings. Don't get me wrong, I'm not "impatient", and I'm not wanting to make something happen RIGHT NOW, and I certainly respect and value her enough to want her to move on. I just don't know how I'm going to not drive myself insane with these thoughts for the next 6-12 months.

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