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.

Courtney writes, "I have been in and out of relationships for some time. I am now in a relationship where I actually really like this guy but my insecurities and low self-esteem is ruining our relationship. I did tell him before we started to date that I am very sensitive and take everything to heart and that it doesn't take much to make me upset. I have been trying to change my ways but I need help. He and I had a talked this morning through texting and we almost broke up because he doesn't know how to deal with my insecurities where I am sad and not a pleasant girlfriend to talk to. It hurts, when I have to sit and explain how I feel and get nothing in return. Before we almost ended it, he said that "I like you and I want to stay together to at least try and work on our relationship." We are new in the relationship so any type of advice would be wonderful."

I totally understand how lack of confidence and self esteem can make it harder for you to have a proper relationship. Yep, the girl asks, "Does my butt look too big in these jeans," and if the poor guy says either a Yes or No, he is in trouble either way with someone who has low self esteem. Even a praise can be misconstrued by such a woman as mockery or ridicule or criticism.

I am glad that your boyfriend is supportive and understanding, but not all men are like him, and even his patience may not be infinite.

In other words, you will need to work on these issues (preferably with a life coach) and deal with them head on. He might only bear with you for a while but you need to resolve them on your own. During this period, do not judge him because it is not him, it is you who is drawing the wrong conclusion. If he is not looking at you and looking at a woman passing by, do not assume that it is because you are ugly and the other girl is hot. You get the idea.

Raising your self esteem and getting rid of your insecurities is something that takes time and if you wish I will be glad to help you in that area. If you want to get help from me, sit down quietly, and write down a list of all the things that you hate about your body, your life, and your world, and then email it to me.

Josh writes, "I often get looks and stares from girls about being tall. I am only a little over 6' 3. I am concerned about this. I do not feel that women treat me seriously. I do not look for relationships but often feel threatened by them. I sometimes attract older women which is uncomfortable for me. I have realized that dating older women is not for me because of my low self esteem. I also get laughed at by other guys of my race (African-American). I do not wish to start anything confrontational with people, but it seems that people may be threatened by me or something else. I know that I am not paranoid, but I do notice something wrong or a change. My idea is not to attract a lot of girls, but good people. How should I go about this?"

Actually, height is a big advantage and almost all women like tall men, though, very short women maybe reluctant to approach you because they know that you may not like short women and it will be an incompatible match. In any case, you should not feel bad about your body that you were born with, as long as you do not have a big tummy or are not fat because that has health implications.

Regarding being taken seriously, well, you have to be serious first. If you are always kidding around, then, no one take you seriously.

During recent years it is common for older women to chase younger men and that should make you feel nothing different than a woman your age chasing you. However, if you are not interested, you can politely say that you are looking to date someone around your age.

As you have admitted yourself, you seem to be way too conscious of yourself and that has led to lower self esteem and lack of confidence. You have a victim mentality and imagined fears that others are out to get you. That is not likely the case -- most people are so self-absorbed these days that they hardly care how others look or behave.

Raising self esteem is not something difficult to do. You do seem to be liked by girls and all you need to do is to go out there and conquer the world. If you have access to a mentor or life coach or counselor or a good friend, I strongly suggest that you reach out to him to help you build your confidence, develop positive body image, not just for falling in love but also in other aspects of your life, like career.

Simon writes, "I have a good friend who is a bit of a busty woman. I want our bond to become closer. I want to make love to her. She has not said that she does not want it in our relationship but she seems uncertain. She seems cautious. It may be because she is busty that she is hesitant. Might this be the reason? Might there be other reasons why she seems uncertain? How can I get her to think about us being intimate? How can I make her feel comfortable about her body? How can I get her to explore her sexuality? If we do it, are there certain positions that work better for lovemaking with a busty woman?"

It is common to be reluctant about having sex until you are positively sure about a relationship. Sex brings a level of intimacy that is not easy to forget.

I would seriously doubt that her being busty has much to do with it, unless of course, her being busty also means that she has sagging breasts and fat in all the wrong places. Remember that many women with large chests are almost always also fat. Only a rare woman will be busty (without breast augmentation) and be skinny at the same time. If she is out of shape she may have low self esteem and that may be the reason for her reluctance.

In my opinion, sex is the celebration of love. If you demonstrate your love to her and prove that you like her for being what she is rather than some kind of a movie star, she will understand that you will accept her body as it is. You can enhance her self esteem by praising her looks and making her feel good about her body.

Regarding suitable position, I am not sure that there are any, unless she is overweight. If she is too fat then you may realize that traditional position likes missionary or woman on top may not work so smoothly because of the fat in the pelvic area. In that case, it requires a little adjustment so that you can penetrate her all the way.

A sexless marriage can be a disaster and can completely the shatter the self confidence of a woman. But it does not mean that a woman cannot have a normal relationship with another man.

Here is an email from a woman who was previously in a dysfunctional marriage without any emotional or physical intimacy.

She writes, "I am absolutely attracted to men, I DO have sexual thoughts (a lot lately). Now Yes again I do have sex. I currently have a boyfriend and we've been having sex since last 8 months and all I can say is WOW!!!!! I honestly don't understand how I could go from severely disliking sex to LOVING it totally. Honestly my boyfriend is the one who I used to call a nympho but he calls me that now. I mean its not crazy or anything; it's just great sex I can't seem to get enough of. Honestly we do it every single day. We usually never only do it once, it's always twice or more. We have on many occasions had sex 5 times in a day. Anyway I just don't understand the drastic change."

Guys low self esttem

We often assume that only women have self-esteem issues, that they are the ones that keep beating them up for not having perfect bodies. Men too can have low self esteem and lack confidence.

Michael is one such man and he honestly shared his fears with me. "About my looks I am not really sure. Most of my friends are, well, guys I have known for a long time. I have my older sisters and they are all telling me I look good. But can you really trust family with this stuff? And again I am a well-built guy. I don't go to the gym every day. So I am really not sure where I stand, but if you ask me I may be standing on the line of average or below. So if looks are what a girl thinks about, I am not sure if I am still in trouble or what?" he asks.

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Well, first of all, it seems that so many people can't be wrong. If they think you look good, you probably do.

Secondly, even an average guy or girl can look great if you groom yourself properly. Have you seen those girls in the mall that show up in those baggy Tshirts and sweatpants? I hate 'em but I often see that they have great bodies and attractive faces. Still, I am not drawn to them at all. On the other hand, every man is attracted to a girl that makes an effort to put an outfit together and applies makeup the right way.

I don't know if you are the type who wears "whatever," but it is time to change that and girls will notice. Some simple changes like hairstyle, clothes, shoes, and accessories make a huge difference. Wear what you like and feel comfortable in, rather than trying to be someone you are not, but you should look put it all together, in contrast to getting out of bed and simply showing up at a party like that.

And finally, if average guy had no chances, then 90% of men will be single. That is not the case, as you well know. I am an average looking guy like you but am married to a very pretty woman (and have always dated reasonably good looking girls) who loves me for who I am. I pay attention when girls talk, I keep my promises, I show them respect, and I make them feel special. I don't drive an expensive car or tell great jokes or am the life of a party or have anything that makes me really stand out, but so are most girls.

So buddy, just raise your confidence, and don't obsess over your looks. Go ahead and do it -- trust me, it will be easier than you think and there are probably girls out there that keep wondering why you never even approached them.