You can’t have both ways.

*Josh, in Milpitas, has re-acquainted himself with an old girlfriend from his past. They met at 21 and dated. Then, after two years, their lives took different paths. One year ago, 28 years after they broke up, they met up again for the first time at a common friend’s wedding. One thing led to another, sparks flew, and a long distance romance bloomed. Now, after dating long distance for the past 12 months and burning the phone lines, they saw each other only 4 times. Now they’re talking marriage and she is thinking of moving to the state where he lives in order for them to get married. Josh says he is madly in love with her and she says the feeling is mutual.

Josh said that he has done a lot of very dishonest things in his past that he’s not proud of and would be incredibly embarrassed to tell her. He has not being very savvy with money (even though he has turned his life around) and he hasn’t shared that part with her, either. She, on the other hand, has led a very productive life, has become a very successful person in her own right, and was able to retire at a very young age. Therefore, money will never be a problem for her.

He is also very educated, but a car accident left him with some physical limitations. Due to this problem, he is unable to work full time which doesn’t earn him a lot of money. He is a man of modest means and he told her that when she comes to join him in matrimony, she would have to give up her money. He would support both of them. She apparently agreed. Josh has tried to talk to her and ask her what she will do with her money, but she either evades the question or never gives a clear answer.

Another thing that is bothering him is that his car was stolen and he didn’t have a way to get around. Knowing his precarious situation, she didn’t offer to help him out with his car or offer to perhaps get him some kind of transportation, or even give him some money to help him out a bit. The worst thing is that she goes on many vacations instead of coming to visit him since he cannot afford to go visit her as often. He’s feeling very uneasy and insecure about this relationship. He would like to know what he should do to salvage this relationship.

Answer: Let’s go by parts: first of all, you don’t really know who this woman even is. You have been dating her long distance for only 12 months and saw her 4 times. That’s not a real relationship, that’s a pseudo-relationship.  Also, the person you thought she was at 21-22 is a totally different person today and you don’t know her. I believe you are infatuated with what she was at 21-22. You hadn’t spoken to her in 28 years, and then a year ago you met her again at your friend’s wedding. Proof that you don’t know each other is that you haven’t come clean to her about what you have been doing these past years, either. You have not been sincere because you aren’t feeling safe with her. I think that you know if you tell her about your past, she may leave you.

Second: she said she would give up her financial position and come join you in marriage, but hasn’t done it yet. Don’t hold your breath. I don’t think she will; and if I knew her, I would tell her not to give up the money she worked so hard to get because she is now enjoying the accoutrements that come with having financial security. She would not be very bright if she did give up her financial security to move to another state to be with a man that she doesn’t really know either. Let’s be honest: she doesn’t truly know the man you have become.

Third: you speak from both sides of your mouth. In one hand you say you want to support both of you and you want her to give her money away. On the other hand you want her to take care of you as you demonstrated when you complained that she didn’t help you or offer you some kind of transportation when you lost your car. I hate to break it to you, but you are not entitled to her money and she should not give you anything. She doesn’t know you. You haven’t been honest with her. You are not married to her yet. You either need to prove that you can take care of both of you, or you don’t.

I believe if you’d been totally honest with her and told her exactly what you thought about the relationship, it would not have brought you two closer. I believe she would distance herself from you. You already have proof that you don’t know this woman well. She doesn’t seem to be as enthralled with you as you are with her otherwise she would visit you instead of choosing to go on her many vacations. Why hasn’t she given you clear answers to your questions?  I think you are simply delaying a heartbreak; but, ultimately, you are the one who will have to make the decision of whether to stay until she leaves you or let her go at once. How to salvage this relationship? You need to have an honest conversation but you seem unwilling and by avoiding the hard conversations you are simply postponing disappointment. Whatever you decide, I wish you well.



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