Am I crazy even thinking about pursuing this?

You are not crazy for feeling the way you do, She is in the wrong and is using you, She sounds like she wants her cake and eat it too, I would be very upset if I were in your situation, You deserve better and a woman that really is in Love with you, Why torture yourself with seeing pictures of them together happy, Obviously she has feelings for her boy friend and she is not going to leave him for you, I am not trying to hurt you with what I am saying, I am just being honest, Yes it hurts and yes it sucks but you must move in and find some one new, Dont let her use you any more your more important than that and I am sure there are alot of women that would live to be with you and have the same qualities, I am sorry you are going threw this, I hope things get better for you soon

After reading your responses and the other posters you should not pursue this at all. I understand the feelings you have for her may be hard to get around but the fact is there are a few things going on.

first off you are asking here because internally I believe, you know this is wrong, something is not sitting well with you about the situation and you need confirmation or a solid push in the right direction because you are unsure. Many times our gut feelings are right and if I am correct, your gut is right here too and this is not a good situation to pursue.

She is wrong in saying to any other man when she is in an exclusive relationship that she loves him. She not only has told another male this but one that it seems she is aware has feelings for her so it seems to me that it could be very likely she is using you like others have said here. This is called an emotional affair when it does not involve the physical (yet) but nonetheless is just as adulterous and is deceitful on her part. If you are allowing yourself to get involved in this more you are going to be a part of that affair and just as responsible for this.

Her boyfriend. Is it fair to allow this to go on, when he clearly understands on some level that she is getting attached to you and being emotionally involved with you? Put on a pair of his shoes, imagine your girlfriend telling another man she loves him and sharing her deep dark secrets with. Would that concern you? Would you not feel betrayed and cheated on?

IMO for the bf, I think he should break it off from her because she is clearly not a trustworthy person. For you, not only should you walk away from this because of the fact she has a bf but because right now she is proving also to you that she's not trustworthy and likely (very likely) this is something she would also do to you.

Think, please.

I'm sorry you're hurting. I think you're too vulnerable to pursue more with her especially in light of your last relationship.

It's not really relevant, but I wouldn't be surprised if she ditched you and him and started up with a new man. You deserve better. She has issues and it's not because she's young.

Take care.

You should stop pursuing that! She is CHEATING on her boyfriend, if she does that to him why do you think she will not do the same to you later? I think you should let her go and look for someone better.

If you never interact with her again, intense thoughts of her will leave eventually. Time will heal a broken heart. Time will not heal regret.

To stop thinking of her because other people telling you you should stop pursuing her or stop thinking about her, that does not work. Just like you can't decide what you dream about. All you can do is for the actual choises you make is to make them all so it help's you forget her quicker.

May be a very long time. Some people claim they can fall in love with someone else and that helps them forget. I can see how the idea of having more options can help or can be soothing, and you definitely need to maximize interactions with the right type of females to increase success. But I don't understand how a person that is in infatuated with person A can become infatuated with person B. The first infatuating has to stop first.

Thanks guys for all the replies.
Anyway, I can't never interact with her again, I'm a Personal Trainer and she is a client of mine.
Yesterday it was the first time we got to talk after I told her it would be best not to interact like we used to anymore, and she was pretty mad about the whole situation and the fact that I "ruined our special friendship".

Time. Tell her it's over and go no contact 100%. Any pics, videos, voicemails, FB friend. Delete ALL.

Mainly time. Do you have hobbies? Play golf with the guys? Ask a lady on a casual date (coffee, etc) if the opportunity presents itself.

so you'll be around her regularly still? not to sound immature, but she "friended you" with that comment. she's not interested in you. remember her words. take care.

Unfortunately I'm in a very bad situation socially wise. I just moved back from the US to Italy after 8 years because my previous relationship fell apart (and oh boy, THAT was disfuncional). After 8 years, I'm basically a stranger in my own country. I have very few friends to hang with. This 20 year old client was one of the few people who kept in touch while I was in the US.
It's not that easy for me to go out with friends and meet new girls.

You have a fresh start, I think it is good. We all need affection and love...but we need to love ourselves first. The past two ladies...things have gone wrong in significant ways, it seems. Maybe you can talk to a therapist and get insight and guidance on meeting a woman that will treat you with care and respect? Explore yourself and how to be at peace alone and form healthier relationships. Looking back can help us look forward.

Wherever you move, you move with you. If you have any issues (who doesn't?), they followed you. You have "down time" in the social sense...how about making this time about you? Get to know yourself and a therapist can guide you, as well as help you through the grieving process from the recent young woman that mistreated you.

You aren't at fault or unworthy...I think you deserve more and need help discovering that path. What do you think?

You might find it more helpful to post in the Sex and Gender issues forum. You can post about your sexual interests at length there. That said, I would discourage you from pursuing sexual relationships with your clients. Even if you have no license that you are jeopardizing; you are running the risk of a client claiming you did something inappropriate -- even if she appeared to welcome it at the time. Better to hunt for sex partners outside your job.

Sorry mate, this seems like a pretty clear no-go in my book. I couldn't care less about the age difference. Some people may not like it but she's old enough to make her own decisions and manage the ups and downs as they come. However, she is in a relationship. As a general rule of thumb, thats a pretty big "nope" flag, heightened in this case by the fact that you have little (if any) reason to believe that she will leave him for you, and indeed have good reason to believe theyll continue to be together for a good while. Obviously theres issue with going after someone who is taken, but skimming over that, youre just setting yourself up to get emotionally screwed over, more so than you may already be.

Side bit, has she expressed any interest past friendship with you? It seems clear that she isnt likely to leave her existing relationship for you, but Im a little uncertain as to if shes actually expressed any interest in you, outside of that. If not, I feel it only adds weight to my words.

If she is your client then engaging in sexual stuff like her sending naked pics and you encouraging it is very inappropriate. Terminate it with her and her new clients.

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I thought he moved to Italy?

Yes and he is her trainer. That's why he said he can't stop seeing her as she is his client

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The one thing I am confused about is her keeping in touch while you were in the us for 8 years. If she is 20 now was she 12 at the time?

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Okay if i can be real for a moment. First go you! 20 year old wanting to be with an old man like you. Please tell me your secret. Listen man i wouldnt fall for her or put so much of your heart and feelings into this. IMO this seems only to be a fling for her. You dont have to take my advice but look what happend to Paul McCartney chasing after a younger chick. Not to mention say she does leave her bf to be with you. Say eight years down the road she wants kids. Do you really want to change diapers and chase a toddler at that age? Or what if two years down the road she starts wanting to go partying and clubing. Just imagine all the other guys shes going to meet who are going to be trying to hook up with her which could lead to her cheating on you. Then the part of meeting her parents.

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Boraz. I've always believed that age is just a number, and in some cases it's true. I'm 69, but i have a history of seeing men much younger than me. The feeling was that men around my age were boring, lacked energy, and other such nonsense, including not allowing me to be myself.
Until i met this one. He's 76. And other than the problems you might have read about here (mostly from his cranky mother), he's everything i found I needed in a man and then some. Yes, though he gets around, he does have health issues, serious ones too, but mentally he's at my speed and I'm enjoying him, and I'm not referring sexually. Our conversation is delightful, he acts like a gentleman because he is, and not a "I gotta prove I'm a man" mentality I've been accustomed to because I felt only men younger than me can give what I wanted.
My point? Get someone your age. Yes, it's flattering to have a fine young thing "sweating" you. But how better it is to have someone loving you, respecting you, and respect other people.

ok a couple of clarifications.
divine1966: I lived in the US for 8 years but I did a lot of back and forth because of visa issues (my previous gf is an American citizen, the plan was for us to get married and for me to get a regular visa, but at the end of the day she didn't wanna get married, so I ended up doing a lot of back and forth for 8 years and finally breaking up with her). Last year, during one of this back and forth I met the 20 year old girl and she became my client. I do a lot of online training (I send clients training programs and nutritional plans, they report back with their stats, and so on), so we kept in touch, but soon the communication started to be too involved and messy on her part (like I said, pictures, videos, messages about how I changed her life and because of me she feels different, and things like that).
twilliamsjr79: I don't consider myself old . I actually look younger than my real age and being a personal trainer I'm in perfect shape. I actually have a lot of girls younger than me around.
Anyway, it is just a fling. I guess it'll pass.