Dear 100 Hour Board,
How do I stop feeling self-conscious about what other people might think when I date guys who might be considered less conventionally attractive relative to popular media standards of beauty?
Unfortunately I know for a fact that I have judged others in the past for this very thing, but I have no idea why I did that.
-My Name Here
I think the first step is probably accepting the fact that you do have these kinds of feelings. While people don't like admitting that they rely on public opinion to the extent they do, I think societal standards have a very real impact on our emotions, and that we often feel uncomfortable to violate these expectations. If you want to combat such feelings of discomfort, I think it's vital to be aware of when you are experiencing these negative emotions. Perhaps you can try evaluating how reasonable/well-founded your self-consciousness is when it starts to come on.
Besides building awareness, my biggest piece of advice is to let yourself fully enjoy the fun moments you have with these less conventionally attractive guys. In my own life, I've noticed that when I'm having fun, I tend to be a lot less self-conscious.
I think this is a good indicator of where you are in the relationship. I believe that when you find the person that you're supposed to be with, you no longer care about what others think. Neither Ms. Mitty, nor myself fit the traditional "Hollywood" standards of beauty (I mean does anyone really?). However, neither one of us feels self-conscious about the other.
You need to ask yourself why. Why do you feel self-conscious about how your significant other looks? Is it because you do/don't feel like you fit those standards? Do you just need to date more attractive guys? Is it something that can be could be overcome if the guy has a great sense of humor or adventure or something else? That may sound shallow, but by identifying the why, you can address it, and hopefully not feel self-conscious in the future.
I do the same thing. That behavior seems to correlate with my current level of general insecurity. When I feel like I know myself, what I'm doing, and why I'm doing it-- in my life as a whole -- I don't worry as much about what others think. Keep in mind, attraction has two faces. One is important and the other is not. One face is all about status and conventional attraction. The other is how you actually feel when you are with them, when you look at them, and when they touch you. As I'm sure it has occurred to you, conventional attractiveness doesn't matter because it doesn't necessarily lead to personal attraction. I can see an attractive guy and say "I know he is attractive and that many girls would want to date him." and still have no actual feelings of attraction for him at all. Channing Tatum is a prime example. I know girls like him. He's conventionally attractive. But I think he looks like a thumb-thumb.
My advice is to gain as much confidence as you can in your ability to make judgments and decisions for your own life. The better footing you have in your independence, the less you will think about who's looking and why. Try to know yourself well enough to say "Yes. I am feeling ____. I know _____. and I want ______." about good things in your life. Then you can be honest with yourself when you are feeling attraction for someone who may not be conventionally attractive.
When I'm insecure about something it always helps me to think about what I would say if someone asked me why I'm doing it. If I have a legitimate good reason for doing that thing I stop caring what people think, even if they will never know that good reason. It's the best. If you can say "I like him and I want to date him" there's nothing to judge! Case closed. Conversation over. If you feel that and live it you may never even need to say it out loud. Most people, when met with rock solid confidence, will retreat from judgment and start their assessment over again. Your friends and family may think "you can do better." But if you express confidence in the relationship and your ability to choose they will stop talking and start looking for the qualities you are seeing in your significant other.