Virgo woman and Leo man's complicated story...

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virgoproblems
@virgoproblems
6 Years

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I have a huge back story and complicated history with a Leo man and would like some thoughts on our synastry and composite.

It is basically a roller coaster ride of emotions with this man, abrupt breaking up and getting back together, half-stalking each other and hurting each other, and yet, after all these years, I have found myself finally admitting to myself that I love this man. For some reason. It took me almost 15 years to do this, and I want to tell him, but fear is keeping me back.

Long story short, we grew up parallell with each other, same age and saw each other a lot during our teens, crushing hard on each other from a distance.

Things always got in between during those years, but I still remember the first time we locked eyes - it was a sort of "fated" feeling that I have only experienced once since.

Sort of like time slowing down. And trust me, I'm neither a real romantic or idealistic in that way - I'm a Virgo Sun, so practical and shy about love, but with a burning Scorp Moon and Venus...

When we reached our 20s and were both single, he pursued me aggressively (I rejected him the first time when were in school as I was dating somebody) and we ended up in a physical relationship with the best sex of our lives, and possibly the greatest passion for us both. I know for a fact (he told me) that none of have ever had a physical connection quite like it before, or since.

With this came terribly intense fighting and complex emotions as well, even though I tried so hard (I don't know why) to keep the relationship platonic. It was impossible, it would seem. There was jealosy, control issues and intense emotional reactions to everything he did, and I did.

I did some terrible things to him - I was withholding, scared, controlling and emotionally cold to him. He was aggressive, jealous, put all his feelings on display, so far as to saying we should be a couple for real, saying he didn't want to see anyone else and asking why I never wanted to date him "for real",

- to which I had no response and I avoided the issue for months as a consequence.

We both dated other people during this time - it ended when I started dating his best friend. I know that sounds horrible, I don't really understand what I was doing myself, except that I was so scared of the intensity of this relationship and how strong he was coming on to me that I would rather ruin it and get out than admitting I had feelings for him. That's how much this man has scared me.

He has still - yes, even though I dated his best friend and rejected him - tried to pursue me on and off for years - even when he has been in other relationships. Neither his feelings nor mine ever died out - the attraction is so strong that even friends I've been with who don't know our history together have pointed it out. People around us have been simultaneously against us and fascinated by our story.

We have been at a lot of mutual friends parties and places together through the years and he shamelessly will stare at me, always with a sort of aggressive but hurt look in his eyes.

I find myself constantly coming back to this relationship in my head, year after year. This has been going on for almost 15 years now, we are in our early 30s now.

He moved away a year ago so I don't ever see him anymore - yet he haunts me in my dreams even though I try to forget about him. There will be six months without me thinking about him at all, focusing on work or other guys - but it always comes back to this.

We have nothing in common as far as our tastes or interests go and we are certainly not similar as people either - yet the attraction is like NO OTHER, ever.

We started talking recently again - he is very suspicious and guarded towards me, which is understandable.

Do I pursue this for a fourth time? How do I talk to him about this - there is so much unfinished business here and I wish I could tell him how I feel but I'm still so scared, for some reason.

Me - Virgo Sun, Scorpio Moon, Virgo Mercury, Scorpio Venus and Cap Mars

Him - Leo Sun, Aries Moon, Cancer Mercury, Virgo Venus and Cap Mars.

Outer planets for us are the same as we are born close together.

Some of synastry, me being the first and him the second:

Mars trine Venus

Sun Conjunct Venus

Venus Conjunct Pluto

Jupiter Opposite Venus

Asc conjunct Mars

Asc conjunct Venus

Mars conjunct Mars

Sun square Uranus

Uranus square Venus

Venus square Sun (double whammy)

Venus sextile Neptune

Saturn trine Sun

Pluto square Sun

Sun trine Mars

Saturn trine Moon

Both our Moons in each others 2nd house, his sun, venus and merc in my 7th house,

my saturn in his 2nd house, my venus in his first house, my pluto in his first house and his pluto in my 8th.

Our composite include Moon square Pluto (yikes), Moon trine Venus, Venus square Mars, Saturn conjunct Asc,

mars and saturn in first house, Moon in the 2nd house, NN in 5th house, Chiron in 7th house, Sun in the 8th house and Venus in 10th house.

Any thoughts? This is all so confusing, and consuming to me. Trust me - I have really tried to forget about this man but after 15 years, it is impossible and I am now considering giving myself completely to this relationship once and for all. Do we stand a chance?
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virgoproblems
@virgoproblems
6 Years

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Posted by alario

Aries moon and Scorpio moon is a disaster. This is textbook shit. As an Aries moon myself please leave him the fuck alone if you’re not 110% in at this point. He’s shown you for years and you’ve been hurting him the entire time.


Thanks for the honesty. As an Aries moon, it's all or nothing I guess? I'm sure about my emotions but I'm scared of taking action. I guess I should back off until I get that shit sorted out and also be prepared for rejection. I wouldn't blame him.
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virgoproblems
@virgoproblems
6 Years

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Posted by alario
Posted by virgoproblems
Posted by alario

Aries moon and Scorpio moon is a disaster. This is textbook shit. As an Aries moon myself please leave him the fuck alone if you’re not 110% in at this point. He’s shown you for years and you’ve been hurting him the entire time.

Thanks for the honesty. As an Aries moon, it's all or nothing I guess? I'm sure about my emotions but I'm scared of taking action. I guess I should back off until I get that shit sorted out and also be prepared for rejection. I wouldn't blame him.

From what you’ve said he’s been all in the entire time. If he’s pulling back now and you still want him you’ll have to be brave and put yourself out there. Aries moon doesn’t usually lie about where we’re at so it’s most likely he will tell you if there’s still a shot.
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The last time we tried this, four years ago, I took steps forward to sorting this out - we were supposed to meet up a week from that, he never called.... until TWO months later when he asked me out for a date, all of a sudden.

Those kind of things also kind of broke my trust to him, who unfortunately has a bad rep around women - he's been a bit of a man whore. I've had a hard time getting past that. I don't understand how someone could back out of meeting someone and then expect the other person to fully just be waiting months later for them? No explanation.
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Greylatern, The Laughing Heart
@Lostthoughts
6 Years1,000+ Posts

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Disclaimer: I stopped steading Astrology at composite charts. So I'll just stick with what I know. I also believe very few challenges can not be overcome, if your willing to put in the work and have a open mind on how.

The aspects you list in composite does support what you are saying. Pluto moon is manageable. I wish you posted pictures to get better detail sign and house matter. Chiron7th would mean you both have trouble agreeing on things and breaking them, not just one person. Wether you realise it or not you hurt him too.

It's something your going to have to let go of and start over. Chalk it up as a learning experience with each other.

Pictures as so much better then that format. I would also look at, lilth h13, Ceres, Juno, Vesta, Eros, and pyche and look for strong aspects. Those play a big part in relationships, when there is aspects.

Are you sure, like 100% you want this though?

The thing people don't understand is, sometimes you do work but not the way you want it to. Being that open minded...

That's tricky.

You guys have so much energy between you the challenge isn't your past, it is actually doing something with that energy instead of using it on each other were it doesn't work.

Your description of events and charts screams catalyst relationship to me. Designed to spur personal growth in order for it to work or just self development in general. Basically in the relationship you can not rely on the other person to fullfil all your needs and desires in life. What works works and what doesn't you need to put your heads together and compromise or find outside of the relationship. While still being very supportive and helping each other with their endeavors outside the relationship. A partnership.

The relationship and your feelings for each other can never be questioned. Insecurity and fear is death 100% . Being open without judgement isn't easy. Ride or die.

Your best bet is to put all your cards on the table. Tell him how you feel and why. Talk to each other and find out what went wrong. Don't argue about it. Instead just look at it like a exchange of information and hash it out. Expect a lot of things that happened between you two stem from emotional misunderstandings and ignorance. You were both young and stupid once. Forgiveness and understanding first then effort and commitment.
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virgoproblems
@virgoproblems
6 Years

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Posted by Lostthoughts

Disclaimer: I stopped steading Astrology at composite charts. So I'll just stick with what I know. I also believe very few challenges can not be overcome, if your willing to put in the work and have a open mind on how.

The aspects you list in composite does support what you are saying. Pluto moon is manageable. I wish you posted pictures to get better detail sign and house matter. Chiron7th would mean you both have trouble agreeing on things and breaking them, not just one person. Wether you realise it or not you hurt him too.

It's something your going to have to let go of and start over. Chalk it up as a learning experience with each other.

Pictures as so much better then that format. I would also look at, lilth h13, Ceres, Juno, Vesta, Eros, and pyche and look for strong aspects. Those play a big part in relationships, when there is aspects.

Are you sure, like 100% you want this though?

The thing people don't understand is, sometimes you do work but not the way you want it to. Being that open minded...

That's tricky.

You guys have so much energy between you the challenge isn't your past, it is actually doing something with that energy instead of using it on each other were it doesn't work.

Your description of events and charts screams catalyst relationship to me. Designed to spur personal growth in order for it to work or just self development in general. Basically in the relationship you can not rely on the other person to fullfil all your needs and desires in life. What works works and what doesn't you need to put your heads together and compromise or find outside of the relationship. While still being very supportive and helping each other with their endeavors outside the relationship. A partnership.

The relationship and your feelings for each other can never be questioned. Insecurity and fear is death 100% . Being open without judgement isn't easy. Ride or die.

Your best bet is to put all your cards on the table. Tell him how you feel and why. Talk to each other and find out what went wrong. Don't argue about it. Instead just look at it like a exchange of information and hash it out. Expect a lot of things that happened between you two stem from emotional misunderstandings and ignorance. You were both young and stupid once. Forgiveness and understanding first then effort and commitment.

Thank you! I think we're both on the same page here, and I came to terms with a lot of stupid stuff I did back then, and most of the stupid things I did in relationships was with this guy for some reason. It was an eye-opener for me to re-read old messages and see things from a different perspective years later. I take on a LOT of responsibility for what happened between us, I fully admit to liking being the one in control, playing mind games and enjoying making him jealous, because I definitely did that on purpose. I liked how he reacted so strongly and possessively; though I'm not sure he liked it. He is used to taking a more player-type role with girls and not be that emotionally invested.

The last time we dated, he was very insecure with me, very shy and basically so nervous he couldn't be still around me. Nothing like the confident, cocky 20-year old the first time we were dating.

I don't know a lot about Chiron or Chiron in the 7th, what do you mean trouble agreeing on things? Both very stubborn in our ways? Because we do lead very different lives and always have. I feel like we both have become slightly more neutral about it with age, though.

Do you mean that relationships in general can't be denied, or this one in particular? I always felt like the air literally becomes thick as soon as we're in the same room together. I remember sometimes when we were at the same events with the same people - not on purpose, mind you - and I remember having to LEAVE the room if he was in it because it would literally get that intense, even without talking to each other. That, and he would always, shamelessly, stare me out.

I can definitely get pictures of our charts.

I do know we have positive Juno aspects, like Juno conjunct Saturn and Juno trine Sun.
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Nameless Nemean
@Chuckcem
14 Years5,000+ Posts

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As complicated as this may seem, it's fairly simple. This is not a healthy situation, not even in the slightest. Leos do not trust people who are not open, regardless of our own disposition. If you can not be honest with the Leo, there is no hope of this ever working. Also think about it, as many times as you have rejected the Leo in the past, why should he suddenly take you seriously now?

To be honest, there seems to be so much bad history between you, that I couldn't in good conscience recommend that you pursue this. I'm sure the Leo was no angel, but dating his best friend out of what appears to be spite, points to something toxic. If you can't be honest with yourself about your own motivations (both past and present), then I strongly recommend you do not pursue a Leo.

Lastly as you have already stated, you have nothing in common. That is a clear sign that the two of you are not designed for one another. Sure there may be physical chemistry and history, but good sex does not make a healthy, worthwhile relationship. It was just good sex, time to let it go.
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virgoproblems
@virgoproblems
6 Years

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Posted by Chuckcem

As complicated as this may seem, it's fairly simple. This is not a healthy situation, not even in the slightest. Leos do not trust people who are not open, regardless of our own disposition. If you can not be honest with the Leo, there is no hope of this ever working. Also think about it, as many times as you have rejected the Leo in the past, why should he suddenly take you seriously now?

To be honest, there seems to be so much bad history between you, that I couldn't in good conscience recommend that you pursue this. I'm sure the Leo was no angel, but dating his best friend out of what appears to be spite, points to something toxic. If you can't be honest with yourself about your own motivations (both past and present), then I strongly recommend you do not pursue a Leo.

Lastly as you have already stated, you have nothing in common. That is a clear sign that the two of you are not designed for one another. Sure there may be physical chemistry and history, but good sex does not make a healthy, worthwhile relationship. It was just good sex, time to let it go.


Oh, it wasn't out of spite - I did happen to actually really like his friend, but in part, you're right. I mean - you don't date somebody's best friend if you have true feelings towards them, it's just wrong. It's fucking terrible actually. I would never, ever forgive somebody for that and I sure as hell would never date them again after that.

I don't know what went through my head at that time - except I was very immature, and I told myself time and time again that Leo wasn't serious about me anyway. That it was just physical so he wouldn't care who I was with anyway.

I'm trying to be as honest as I can - that there IS something more beyond the physical between us. That's the point I want to make to him and also, for the first time, once and for all, take accountability for what I did to him and for the first time acknowledge my feelings for him.

I mean, the rest is up to him, I really don't expect that much, I wouldn't blame him if he couldn't trust me. But I really need to see if we CAN make it work as adults - or if it's still toxic, like you say, because it damn sure was toxic back then.

People change, though. I know for sure I did.
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virgoproblems
@virgoproblems
6 Years

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Posted by SeaLion

Sounds like you have a very Plutonic relationship. Those are the worst and hardest to get over. I've been there with a Libra and a Pisces. The Libra spanned over a decade and I still know him but have been avoiding him since I met the the Pisces which was almost 5 years ago. I dont talk to either now and I feel better about it.


I think we only have Pluto square Sun and Venus Conjunct Pluto in synastry, but it's always felt HEAVILY plutonic to me as well. Like inescapable, really.

We don't talk either but I still dream about him and then it's, you know, ruined for the next couple of months where I will be constantly revisiting feelings and memories about him. I don't do this with any other ex, so it's nothing to do with as a person really. I don't know why it keeps happening - I'm fairly certain that, before he moved away, it was the same for him.
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SeaLion
@SeaLion
7 Years1,000+ Posts

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Posted by virgoproblems
Posted by SeaLion

Sounds like you have a very Plutonic relationship. Those are the worst and hardest to get over. I've been there with a Libra and a Pisces. The Libra spanned over a decade and I still know him but have been avoiding him since I met the the Pisces which was almost 5 years ago. I dont talk to either now and I feel better about it.

I think we only have Pluto square Sun and Venus Conjunct Pluto in synastry, but it's always felt HEAVILY plutonic to me as well. Like inescapable, really.

We don't talk either but I still dream about him and then it's, you know, ruined for the next couple of months where I will be constantly revisiting feelings and memories about him. I don't do this with any other ex, so it's nothing to do with as a person really. I don't know why it keeps happening - I'm fairly certain that, before he moved away, it was the same for him.
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Text book plutonic
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taurus sun/rising cap moon aries mercury/venus pisces mars
@notreally
6 Years500+ Posts

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I would have to put myself out there and go for it if he was still interested. You will always be disappointed with yourself if you don't. You've already said that he is a fuckboi so perhaps this is just a chemistry attraction that you've both made sound like something else. But don't fool yourself anymore. Call his bluff. You will soon find out if it's real or not. Sometimes you have to take a chance to get to the truth.
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virgoproblems
@virgoproblems
6 Years

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Posted by notreally

I would have to put myself out there and go for it if he was still interested. You will always be disappointed with yourself if you don't. You've already said that he is a fuckboi so perhaps this is just a chemistry attraction that you've both made sound like something else. But don't fool yourself anymore. Call his bluff. You will soon find out if it's real or not. Sometimes you have to take a chance to get to the truth.


He most definitely has been a fuckboy - but also, interestingly, capable of longer relationships. I don't know what went down or why they ended - but he is very close to all three ex girlfriends still so he can't have been that much of a cheater, or at least there seems to be little or no ill will between any of them.

I know for a fact he is looking to settle down and get married. He made some huge transformations in his life and attitude during the past two years. We haven't really spoken that much so I can't be certain if anything has changed between us though - I just know for a fact it's more than just sex and it's always been more. There's something else blocking but it's hard to pinpoint what it is. It's been 15 years off and on and I am definitely not the type of person who lingers around past lovers - when I'm done, I'm done. Except with this one.

We have pretty excellent synastry but he has some worrying aspects of his own in his natal chart, like Venus square Uranus, Moon square mars and Venus square Chiron.. I guess a lot of that points to fear of intimacy - but way back when we were just fuck buddies he would constantly be asking ME for more intimacy and I was actually the one with the problem - stuff I have sorted out since then.

I guess I'm just asking - how do you work with these bothersome aspects? My view of him is of someone who believes themselves to be a lot stronger than he is, obsessed with what kind of image he has outwardly, he really wanted to be a fuckboy but in fact is terrified of being alone, with low self esteem and body issues - and I think he's always dreamed of some ideal mate stronger than he is to hang on to... Just my observations after 15 years on and off with him..
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virgoproblems
@virgoproblems
6 Years

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Posted by LostinmyMind11

Damn we may know the same leo 😂....I'm kidding.

Just tell him what you're telling us here....do you really wanna go another 15 yrs of what ifs? Leo's are great but I think it takes a lot of time for some of them to evolve due to their big ass egos lol.


Yeah and add an Aries Moon that I think has been out of control for a bit as well, haha. He's a good person, the side of him I saw when we were dating is a side other people don't seem to see - I'm hoping that's what he is evolving towards.

I'm still scared though, and that's a problem - I really need to decide on this. Not sure what's still scaring me - I'm also obviously capable of long term relationships.
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LIMM
@LostinmyMind11
14 Years10,000+ Posts

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Posted by virgoproblems
Posted by LostinmyMind11

Damn we may know the same leo 😂....I'm kidding.

Just tell him what you're telling us here....do you really wanna go another 15 yrs of what ifs? Leo's are great but I think it takes a lot of time for some of them to evolve due to their big ass egos lol.

Yeah and add an Aries Moon that I think has been out of control for a bit as well, haha. He's a good person, the side of him I saw when we were dating is a side other people don't seem to see - I'm hoping that's what he is evolving towards.

I'm still scared though, and that's a problem - I really need to decide on this. Not sure what's still scaring me - I'm also obviously capable of long term relationships.
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The Leo I know has a Aqua moon which is also a Hades moon...so he has that opposite and darkness that resides in him but like you...I see the good in him. He's fucked me over and played games with me so many times in the short amount of time I've known him but for some reason...I cant even be mad at him and I'm probably the only person that accepts him for him that's why he keeps coming back. But I'm done with us trying to be anything more than friends and I'm glad I put myself out there with him (I've done things for him that I've never done for other people, I've never had the urge to get married either but I could see myself marrying him...I won't but I could see it)....cause now I can move on from being all googly eyed with him (it was a plutonic deal where I was Pluto and we have sun/moon conjunction) and I'm free from the obsession.

Take the leap...life is too short to wonder and if anything it may help in finally moving on from him if it doesn't go as planned. Just don't go in it trying to fix him...you know us Virgals like a good fixer upper lol.
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taurus sun/rising cap moon aries mercury/venus pisces mars
@notreally
6 Years500+ Posts

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Posted by virgoproblems
Posted by notreally

I would have to put myself out there and go for it if he was still interested. You will always be disappointed with yourself if you don't. You've already said that he is a fuckboi so perhaps this is just a chemistry attraction that you've both made sound like something else. But don't fool yourself anymore. Call his bluff. You will soon find out if it's real or not. Sometimes you have to take a chance to get to the truth.

He most definitely has been a fuckboy - but also, interestingly, capable of longer relationships. I don't know what went down or why they ended - but he is very close to all three ex girlfriends still so he can't have been that much of a cheater, or at least there seems to be little or no ill will between any of them.

I know for a fact he is looking to settle down and get married. He made some huge transformations in his life and attitude during the past two years. We haven't really spoken that much so I can't be certain if anything has changed between us though - I just know for a fact it's more than just sex and it's always been more. There's something else blocking but it's hard to pinpoint what it is. It's been 15 years off and on and I am definitely not the type of person who lingers around past lovers - when I'm done, I'm done. Except with this one.

We have pretty excellent synastry but he has some worrying aspects of his own in his natal chart, like Venus square Uranus, Moon square mars and Venus square Chiron.. I guess a lot of that points to fear of intimacy - but way back when we were just fuck buddies he would constantly be asking ME for more intimacy and I was actually the one with the problem - stuff I have sorted out since then.

I guess I'm just asking - how do you work with these bothersome aspects? My view of him is of someone who believes themselves to be a lot stronger than he is, obsessed with what kind of image he has outwardly, he really wanted to be a fuckboy but in fact is terrified of being alone, with low self esteem and body issues - and I think he's always dreamed of some ideal mate stronger than he is to hang on to... Just my observations after 15 years on and off with him..
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I don't know. For me - if there was a move toward a long relationship - I would always be wondering when the ice would break. I prefer a stable person who knows who they are; goes after what they want; and is true to themselves. We all change and grow as we mature. There's a source of his pain which needs attention so that it helps him open up to it; and only then will he be able to grow in the right direction.
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virgoproblems
@virgoproblems
6 Years

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Posted by LostinmyMind11
Posted by virgoproblems
Posted by LostinmyMind11

Damn we may know the same leo 😂....I'm kidding.

Just tell him what you're telling us here....do you really wanna go another 15 yrs of what ifs? Leo's are great but I think it takes a lot of time for some of them to evolve due to their big ass egos lol.

Yeah and add an Aries Moon that I think has been out of control for a bit as well, haha. He's a good person, the side of him I saw when we were dating is a side other people don't seem to see - I'm hoping that's what he is evolving towards.

I'm still scared though, and that's a problem - I really need to decide on this. Not sure what's still scaring me - I'm also obviously capable of long term relationships.

The Leo I know has a Aqua moon which is also a Hades moon...so he has that opposite and darkness that resides in him but like you...I see the good in him. He's fucked me over and played games with me so many times in the short amount of time I've known him but for some reason...I cant even be mad at him and I'm probably the only person that accepts him for him that's why he keeps coming back. But I'm done with us trying to be anything more than friends and I'm glad I put myself out there with him (I've done things for him that I've never done for other people, I've never had the urge to get married either but I could see myself marrying him...I won't but I could see it)....cause now I can move on from being all googly eyed with him (it was a plutonic deal where I was Pluto and we have sun/moon conjunction) and I'm free from the obsession.

Take the leap...life is too short to wonder and if anything it may help in finally moving on from him if it doesn't go as planned. Just don't go in it trying to fix him...you know us Virgals like a good fixer upper lol.
click to expand



Yeah, it's like you read my mind of this - I just feel like the only way I'll be free is truly letting him know how I felt all along and that I do see so many things in him I like. I was fed a lot of bullshit and bad rep stuff from other people about it before that didn't match up to how he was actually treating me - yeah, we played games and were jealous of each other but a lot of times he was mirroring shit I did, I was actually the immature one and I want to apologize once and for all.

I was a dark, foul Pluto in this relationship but I've come a long way since.
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virgoproblems
@virgoproblems
6 Years

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Posted by DMV
Posted by virgoproblems
Posted by DMV

You have no desire to end things. No use in faking it.

This is your life.

Go be with him. Give your all, exhaust every effort.

Do what makes you happy.

I'm so fucking scared though.

Why? You know exactly what's going to happen. It's not like you're walking in eyes wide shut.
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We haven't seen each other IRL for 3 years so it's a bit.. I don't know.. me personally, I changed a lot these 3 years due to heavy, horrible stuff in my family life that played out. I don't know what happened to him but at least I see he made a lot of major shifts in his life as well.

Like I said, I'm ok with no reply and a negative reply but getting a positive reply is like facing my final problem.. which is truly opening up to him and giving this a shot; something I've been unable to do for 10 years.
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virgoproblems
@virgoproblems
6 Years

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Posted by notreally
Posted by virgoproblems
Posted by notreally

I would have to put myself out there and go for it if he was still interested. You will always be disappointed with yourself if you don't. You've already said that he is a fuckboi so perhaps this is just a chemistry attraction that you've both made sound like something else. But don't fool yourself anymore. Call his bluff. You will soon find out if it's real or not. Sometimes you have to take a chance to get to the truth.

He most definitely has been a fuckboy - but also, interestingly, capable of longer relationships. I don't know what went down or why they ended - but he is very close to all three ex girlfriends still so he can't have been that much of a cheater, or at least there seems to be little or no ill will between any of them.

I know for a fact he is looking to settle down and get married. He made some huge transformations in his life and attitude during the past two years. We haven't really spoken that much so I can't be certain if anything has changed between us though - I just know for a fact it's more than just sex and it's always been more. There's something else blocking but it's hard to pinpoint what it is. It's been 15 years off and on and I am definitely not the type of person who lingers around past lovers - when I'm done, I'm done. Except with this one.

We have pretty excellent synastry but he has some worrying aspects of his own in his natal chart, like Venus square Uranus, Moon square mars and Venus square Chiron.. I guess a lot of that points to fear of intimacy - but way back when we were just fuck buddies he would constantly be asking ME for more intimacy and I was actually the one with the problem - stuff I have sorted out since then.

I guess I'm just asking - how do you work with these bothersome aspects? My view of him is of someone who believes themselves to be a lot stronger than he is, obsessed with what kind of image he has outwardly, he really wanted to be a fuckboy but in fact is terrified of being alone, with low self esteem and body issues - and I think he's always dreamed of some ideal mate stronger than he is to hang on to... Just my observations after 15 years on and off with him..

I don't know. For me - if there was a move toward a long relationship - I would always be wondering when the ice would break. I prefer a stable person who knows who they are; goes after what they want; and is true to themselves. We all change and grow as we mature. There's a source of his pain which needs attention so that it helps him open up to it; and only then will he be able to grow in the right direction.
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I think you're right. Even if he's gotten past most of this now, maybe me finally acknowledging our connection and my feelings to him helps bring closure to the whole thing. We all want to know we matter to other people, after all.