Should I breakup with my insecure boyfriend?

Lacie writes, "I just started dating a wonderful 44 year old divorced man. He was married for 16 years and was mentally, physically, and emotionally "done" the last 5 years of the marriage. He's been divorced for a year and has dated previously before he and I met. He is really a sweet man who knows what he did wrong and what he settled for in his first marriage and wants to make things different if he ever gets married again. The problem? He is EXTREMELY insecure. And it's not about sexual inadequacies or feeling like I might cheat on him. Let me give you an example for instance. He has sleep apnea and has to use a C-Pap. Well knew about sleep apnea but really didn't know as well as I could. So I read up on it. I told him about it and told him it could be fatal. Just telling him what I read. His reply: "I don't want you to worry now and every time I get in the bed you'll tell me to put it on." So I explained that it's not a big deal and I won't nag, I was just reading about it. His next statement: "So are you gonna leave me because I have that?" THAT IS JUST ONE EXAMPLE! That is the most minor. There are others about what he thinks are his issues, like his weight, his teeth and all kinds of things that I would not have gone out on a second date with if they bothered me. What do I do because it's out of control and it's early!"

Dealing with a man with insecurities

In most cases, a divorced man comes with a lot of baggage. I mean, he wouldn't get a divorce if he did not have some issues. In your boyfriend's case, it is clear that he was in a really bad marriage that completely drained him. I am assuming that his ex-wife mentally tortured him all these years and put him down every single day. I am guessing that some of his insecurities stem from his inability to have a happy marriage and how it led to a divorce.

As you describe, he is otherwise an awesome man, and that is why worth giving him some time to make things better. Yes, he will take years to get over his insecurities and low self esteem. He will discover gradually that he is a just a normal man that has good and bad things like any other 44 year old man out there and he should get over those. The sacrifice that you will need to make is to not mention what he might perceive as a flaw. It is not easy. If you suggest a cosmetic dentist, he might perceive it as a hint that you don't like his teeth. However, little by little he will notice that you love him for who he is.

Seeking help from friends

Another aspect of his life that you might want to look at is his group of friends. I hope he has good male friends and if not, you might want to hang out with other couples from time to time. As he will talk to males like him he might realize that they are all like him.

So give yourself 3-6 months, if you have the patience, but it is going to be hard and may not work. In that case, it is best to exit at this point and let him deal with his problems alone. If you breakup now, it will be easier on both of you.