Dear Sheila:

You shared that you suffer from a low self esteem, that you were a high school dropout who currently, at over 50 years old, have a job, but not a career. You described yourself this way: “a high school dropout with chin hair and flab”.

Your live-in boyfriend of nearly seven years rubs your feet every night, “truly worships and adores (you).. a good sweet person who has (your) back and always will”, but is “terrible with money”, has an $85,000 student loan that he never paid (and therefore has bad credit), can’t keep a job, and because of all that, you cannot buy a home with you and the two of you moved three times in the last six years.

You “really don’t  like the way he kisses”, he can’t keep an erection and you didn’t try to have sex in a year. He recently had a weight loss surgery that may help with his erectile dysfunction and “There’s so much pressure around us having sex now”, you wrote.

Your dilemma: “I am afraid to leave because I am afraid I am never going to meet someone who’s going to love me as much as he does… feeling like the man I would truly be attracted to would not want me”, and your mother tells you that it is important to have someone who truly cares for you as you get older.

You feel that you are not being fair to him, that you are “living a lie and we’re never going to move forward because of his debt”.

You asked: “Do I have grass is greener syndrome?”- my answer: I don’t think so. You are facing two very practical issues in this relationship: (1) He has a significant financial debt and he can’t keep a job- meaning he is not likely to add to your financial well-being and practical stability in life, such as living in the same place and no longer moving.

(2) You don’t like the way he kisses, and you are not physically attracted to him- how will you feel being naked with him, trying to help him get an erection when .. you don’t want to be there. I imagine that you will try to get it all over with as soon as possible, and let out a sigh of relief when it is over. And then, dread the next time!

Your mother told you that it is important for you to have someone with you who truly cares about you, but I say: it is important for you to not live a lie as you get older, to not carry on a dishonest relationship, and to not compromise yourself in this painful way (a way that is painful for any woman at any age): to be naked with a man and engage in kissing and sexual acts when you don’t want to be there!!!

“How do I tell him how I truly feel without totally crushing him?”- my suggestion: tell him that you are  so sorry, but the two of you must separate and live individual lives. State this gently and empathetically, and make sure that you are not giving him any hope for a change in your decision, so that he can recover from the breakup. As you take the practical steps leading to the separation, be considerate of him- give him enough time to move out (or perhaps you will move out), seeing to it that he has the opportunity to comfortably settle in without you, within his means.

You mentioned having a low self esteem. It is not too late for you to feel better about yourself. It is not too late for you to find a suitable partner for life, one with whom you will feel comfortable in all contexts. This “high school dropout with chin hair and flab” at over 50- is just as worthy, just as valuable a human being as anyone else of any age, educational level, and muscle tone, I say!

anita