Jealousy and Her Past

Visitor's Question from a 21-30 year old Male
I'm involved in a relationship with a woman that is considerably older than I am, and this has led to some enormous jealousy issues on my part. She's been married before, has had several relationships and one one-night-stand. I've had one relationship that lasted 3 years before I met her and that is all. My problem basically revolves around one person, and that is her one night stand. She had just broken up with her love of her life at the time, the person she truly felt was the one for her and she was going through a tough break-up. She said it was the toughest time in her life, which I cannot quite relate to but I can understand. She met a person through the internet, a man from overseas that she had a one-night-stand with that she had no feeling or any emotions for, it was just a one night stand and that was it, she said. She said she hasn't tried to contact him after that, he tried to get in touch with her but never managed to get in touch with her and that was all. Whenever I asked her or brought his name up, she always became very defensive and very very mad. She also once said she took pictures of him before he left her and she said 'I still keep his pictures...', this just set off alarm bells in my head for some reason. I kept thinking and obsessing over this person, I had him pictured in my head as the perfect guy. She described him as being incredibly handsome, with a great personality and he knew how to make her laugh, besides that he was so open sexually and she loved that.

A few months passed by in our relationship which was also not a 'live' relationship yet, as I met her online. We had many arguments over the phone whenever I brought up his name and we never really talked about it, she would just be very mad at me and I felt like she was hiding something. Two weeks ago, we finally met after I decided to fly over to her. Everything worked out great and I truly love her so much. She keeps telling me over and over that I make her so happy and she reassures me on a daily basis by telling me all the things she loves about me, I still couldn't get that person out of my head though, her one night stand. I went through her computer one night and I found a lot of chat logs. About six separate logs and around eight emails from him and it made me feel awful. It was very very very detailed logs about when she was talking to him and how they were planning their first meeting, and how much she was anticipating it. It was then more logs of after their first meeting and they discussed what they did and she kept telling him she can't wait until he can come see her again, which he did the following weekend. She described how she had been so amazingly aroused the entire week just waiting for him and they met up. I read about how he gave her nine orgasms with his hands and mouth and in great detail explaining how they had marathon sessions of sex for tens of hours at a time. She told him in these logs how she felt like she could easily fall in love with him and how she felt very strongly for him, he said for her to cool it off since he had a girlfriend back home so he couldn't get serious. She kept telling him how she wished she could convert him and how wonderful he was. He eventually left, and left her his phone number and she tried to contact him through emails and phone according to the logs. She literally begged him to come see her again but he wanted to leave the experience for what it was, the sexiest and most unique experience they both had.

Ever since this I feel like I can never be good enough for her. I feel nauseous thinking about how she begged for him and how she begged for him when they were being intimate, how he gave her such enormous pleasure and how she was so amazingly happy with him. She told me recently that she does not wish she could un-do that weekend, he was the person who gave her strength to wake up in the morning.

I wonder why she lied to me about it all at first, trying to play it off as nothing happened? This makes me think that it's a sore subject for her, the one perfect guy she's always wanted but never could get, for more than two lust filled weekends. She keeps telling me she wants me now but I can't believe her and I know I can never please her the way he pleased her. I've thought over and over of all the things I've wanted to do with her when I came here but now I just get this apathic feeling of that there's no need to even bother, why should I try make something out of the ordinary when she'll always just think of him and their truly amazing weekend anyway?

It makes me feel like I'm the second-choice, she couldn't have him so she settled for me. This is a flaw that I carry with me from my old relationship where my ex was very very interested in my best friend, and she got together with me to get close to him but after a year she really fell in love with me instead of him, according to her. So being the second-choice does not sit well with me.

The thing is that I love her so much and she makes me so happy besides those times when I start thinking of him. I can hold her and kiss her and I love her so much and want to make her happy, and then a thought of 'them' pops up in my head and I feel awful by just looking at her and imagining them. I feel as if this relationship is going to be ruined because of my jealousy and the fact that I can't ever picture myself getting over this, I will always feel like the second-choice no matter what. Besides going to see a therapist, which I personally don't think will solve a whole lot as I believe the advice would just be that I need to stop thinking of him, cherish the moment with her and realize he was in the past and I'm in her present, but that doesn't work.

I know I will regret it further down the road if I give up a relationship with a woman that I feel is my fantasy woman molded into her, besides her past, particulary with that one person. I've heard the arguments of that her past is what shaped her into who she is, but that doesn't matter to me, and it's not an argument that holds much water with me either.

What is there to do? Leave her and realize that my jealousy makes us unable to be together? I don't know what to do. Advice
Your jealousy will need to be tamed no matter who you end up with. No human is perfect- there will always be people better than you in some way or another for you to be jealous of. You will always be worried that your partner will run off with someone who is richer / sexier / funnier or whatever. You need to work on the jealousy. I have a ton of tips on the site about dealing with that, and of course a therapist can give you more direct assistance.

She can't undo her past. Many people are uncomfortable discussing exs with current partners. I also imagine that given time, you could easily learn exactly what pleases her and be just as fun in bed. Anybody can learn to be a great sexual partner if they want to. Now it's up to you to get your jealousy under control so you don't drive her away in the meantime.

-- from Lisa
One of Your Friendly Advisors at

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