Lilly,

Self esteem issues go way, way back into the time you could barely crawl. So my question, if you don’t mind, what was the relationship with your parents and classmates?

I can tell you this for sure, if your b/f says that you are “pretty and beautiful” believe it. Never fall into the trap of comparing yourself to someone else. Let me share a story with you. Actually it’s not a story, it is real life. A number of years ago I dated this girl who was a model for Surfer magazine. She modeled women’s bikini’s and other clothes. She made her way up the model ladder in a short time. So she had the look-the body, hair, smile, the look. We dated about 5 years, lived together for 4. At first I was liking the lifestyle, meeting people of different levels of high society. I had to attend these openings. I forgot what they were called but they had a show off opening usually, not always, at someone’s HUGE house to showoff their new line of stuff. The first few times I had to attend one of these functions dressed real nice. That wasn’t me. I’m a jeans and t-shirt, and Olukai kind of guy. Apparently a little too laid back for that part of society. So this brought up many fights-what to wear, how to look, etc. I recall one time I was at one of these functions. This guy started making conversation with me. He looked like one of those high end, spoiled rich kids in The Great Gatsby. He asked me, “What do I do?” I pondered for a very short time, sort of perplexed by the question. I asked him, “What do you mean, what do I do?” “Your work. Your line of work. Are you in “the business?” I was assuming the fashion industry. I told him I worked in medicine, specifically surgery as a P.A. I told him that was what I do. His response was, “Oh. I see. Interesting” I guess I wasn’t cool enough for not being in “the business.” so he moved on and found someone he could relate to. One day I decided this lifestyle was too fake for me and eventually left that relationship. Shortly after I met this girl. I was intrigued by her background, how she was able to carry a conversation, but especially her confidence was sexy. I find a woman with confidence very attractive. It wasn’t a snobby kind of confidence, it was real. But she was about an inch or 2 taller than me, I’m 5’9 and a little over weight. But SO WHAT! She looks so much like Mayim Bialik on Big Bang Theory. She was a brunette, had a few acne scars but SO WHAT, she didn’t have the Hollywood requirements for the silver screen but again, SO WHAT!  We talked, shared numbers, and eventually got together. She wasn’t a so-called looker. I loved this woman with all my heart and soul. This relationship ended because she lost her fight with cancer. So what I am trying to say is never compare yourself to anyone else. Never live up to other’s expectations. Your B/F is VERY lucky and when he says you’re are beautiful, believe it.