My boyfriend is insecure about his looks and our relationship.. Help!?!

[Anonymous]

My boyfriend is really self conscious. He is insecure about our relationship and about his looks. He frequently mentions that he’s not attractive or good looking. When he does this, I try to reassure him by saying that I find him extremely sexy and attractive. Unfortunately, however, I feel like my comments are falling on deaf ears because he still repeatedly voices his concerns.

Regarding our relationship, his friends in the beginning were ruthless to him. They asked things like, “How could a guy like him get a girl like me?” and “What does she see in you?” I figured they were just being mean and jealous but it didn’t help his already low self-confidence. This is his first real relationship and I feel like the only thing that will boost his confidence about his looks and our relationship is time. I am hoping that after we have been together for awhile he will trust and realize how much I truly care about him.

Do you guys think that my assumption is correct: That he will slowly gain confidence? Also, is there anything else I can do to boost his self-esteem about his looks/our relationship?

[WarezMyGF]

I use to be the same way as your BF. All the way to the end of high school I was constantly told that I was ugly by my asshole friends and cousins.

After high school I met this hot Romanian model. She had me change my hair style and clothing that looked best on me. After the transformation I realized that I'm an attractive man. Many girls have complemented me on my looks and I've dated some really HOT women. Often when I walk around women will mistep while walking past me, smile like crazy or shy away and look all nervous.

Basically, I know for a fact that I have options. However, sometimes it is still ingrained in my head from my childhood that I'm ugly. I'll have a day or two every year where in my head I'm like "OMG I'm so ugly!"

My current Girlfriend got surprised/upset when I told her the days where I was feeling ugly. She basically sat down with me, looked at me in my eyes and told me straight up that I'm beautiful. Then she told me in detail what physical aspects she likes about me. She wasn't overdoing it either, she was honest. She gave me examples of some of her friends that thought I was hot. Whenever we walk around and some girl is checking me out and I don't notice she will point it out to me and be like "Baby you have a fan" and smile like she's proud I'm her man. With this method she has helped me a great deal. You should try it with him.

[Anonymous]

I’m very similar to your boyfriend but even worse I’d say just to reassure him and tell him all the things that u find attractive in him.. my girlfriend used to think guys were good looking and talk about them sometimes and now she tells me that she think I am the only good looking guy and the only attractive guy is it possible for someone to find everyone ugly except their SO? I’m sorry i hope I helped alittle with my answer but if u could give me feedback on my question that would be so helpful bc I need it I’m falling apart mentally with everything

[Anonymous]

Hit on him randomly, when he isn't expecting it.

I'm in my late 20s but I occasionally have some insecurity issues because of my looks (I'm part redhead...I don't like it). My ex used to call me ginger/dork. I thought she was kidding but now I wonder. It really hurt my self esteem. However I know I'm in better shape than most guys.

[Anonymous]

Try sex maybe it will help, he can brag about it to his friends you know the ones that were puting him down...