Dear Steve,

Her Parents Are No Longer an Issue

This is a very touching and interesting question, that has many variables. The only thing that should not be included in your thinking is whether or not her parents would approve.

I disagree. Her parents may still hassle him.

Don't assume that as a 44 year old woman she would still be swayed by her parents dysfunction. It's one thing when she was living in their home, but those days have been over for a long time.

As to whether or not you should contact her, there are (as usual) two sides to that coin.

You May Be Just a Sentimental Memory

Let me play devil's advocate for a moment. She might not have given you a thought in 20 years. She may be involved. She may be uninvolved, but totally different than your sentimental memories.

And she may resent him for that dose of reality.

I know that I have many good memories about the boy I dated in high school, but I treasure these memories as they are. When I am sad they cheer me up, and I enjoy remembering him as we were then, young and innocent. The last thing I want is to muddy it up with a dose of reality.

She May Need To Apologize

All that said, I don't know anyone that I have thought about every day for 25 years. If I did, I would find it impossible not to contact them sooner or later. I think that's how you feel. Maybe she feels the same way. She probably is ashamed about having bent to her parents wishes, and another meeting would give her the opportunity to apologize, even if she is unwilling or unable to continue your relationship. It could be very healing.

You Need Closure

And have you considered the possibility that your preoccupation with this long-ago relationship is preventing you from finding someone to love who is a real person, with flaws, and not an idealized fantasy?

Maybe this is the beginning of a beautiful love-found-again story - that is the best case scenario. I'm getting goose bumps for you just thinking about it!! But even if it isn't, I think it would be good to contact her. She could ease her conscience, and you could move towards a more reality-based relationship. I don't think this particular memory is healthy for you, if it is keeping you from allowing another woman into your heart.

I am dying of curiosity about how this plays out! Please write back and let me know what happens. Don't forget!! I wish you the best of luck.

– Patra