It’s hard to feel pretty when I feel like my mouth is the size of a cantaloupe, and I can only chew my dinner on the left side of my jaw. Today I had three cavities filled. I’ve never had a cavity in my life (damn those childhood sealants, which apparently become traps for bacteria as an adult).

I should really stop going to the doctor. This year is the year of medical expenses. Every time I go, even for what I think is going to be a yearly check-up, they find something wrong with me. A part of me wonders if this is some kind of conspiracy, but when my dentist showed me the actual images of my cavity-filled teeth, I knew he wasn’t lying.

The procedure wasn’t as bad as I thought. The numbing shots didn’t hurt, and there weren’t any bad smells, but when I left the office, I was oddly self-conscious of my numb face, and the fact that if the side of my face started to droop, I probably wouldn’t notice. So I spent the 20-minute walk home trying to keep my lips shut and avoid any kind of conversation with passersby.

But how is this different from any other day? I have a 10-minute commute to and from work every day. I’m lucky in that DC sense. And every time I make that trek, I am oddly self-conscious. Are my headphones too loud? Can anyone see my underwear line? Can anyone see my lacy bra peeking out beneath my sleeveless top? Is that bulge beneath my pencil skirt obvious? Are there sweat stains beneath my bra line?

Yet even amongst all these questions, I’m oddly confident. I make that walk like I own the sidewalk, and I never look back. I’m aware of my figure, and how good I look in my pencil skirt. But do I ever notice anyone checking me out? No. Do I ever see people look at me? Yep. And I automatically think there must be something wrong with my wardrobe or my headphones aren’t plugged into my phone and everyone can hear my music.

I never consider that people are looking at me because I’m pretty or attractive or because they like my sense of style. But considering the way I grew up, this isn’t surprising. When I look back on my formative years, I cringe at my sense of style and awkwardness. I was never what I would consider a “popular” girl. I never had the attention of guys.

And so I learned that that was just the way it was. Some girls are what Katie Heaney calls “lighthouses” in her memoir. Before I hit my twenties, I considered myself her “Bermuda Triangle.” But once I reached college, I just learned to accept that I was “not wanted by guys.” I learned to love myself and my friends, and I was happy with life.

I even went to prom stag. But I have no regrets. I may have been awkward, but I had tons of friends who loved me. And by the time I graduated high school, I had taken steps to overcome my body image issues and love myself so that I could be the best person I could be.

As I’ve often documented on this blog, that battle with body image is ever going. And even though I’ve been in back-to-back relationships in the past five years, it surprises me that I still have to convince myself that I’m attractive and desirable. I’m surprised anytime someone calls me “pretty” or “beautiful.” Even my ex’s and an OkCupid date. It’s not that I don’t see myself as attractive, but I would never categorize myself that way.

It could be my perfectionism. I’ve never had the perfect body. I still don’t think I have the perfect body. My roommate calls me petite, but I don’t believe her. I know I could be better. I can always be better, but it’s a slippery slope between what is realistic and what is unhealthy. I try to strike that delicate balance.

And I know there are certain things I can’t do such as count calories and own a scale. Those two things go down a slippery slope on their own — combine them and I might as well admit to an eating disorder. No, for me, I know I cannot be technical. I’m too much of a perfectionist and way too self-critical.

This self-criticism is partly my motivation for life. It pushes me to learn new things and challenge myself in new ways. But it can also be my downfall. I hate failing, and if I feel like I’ve failed, it will eat at me until I’ve destroyed myself. I even have to keep this in mind when I berate myself for running a 10-minute mile. I know I can do better, but sometimes the cards just aren’t in my favor, and I have an off day. It’s not the end of the world.

But I am proud of myself for trying to be in the best shape of my life. I have a healthy diet and lifestyle and my diabetes control hasn’t been this good in a couple of years. Even though each doctor visit introduces me to a new dilemma, I have been able to overcome them all. I’m still here.

So how can one have a good body image and a positive outlook on life and yet still be down on herself? How can I not look in the mirror and see the beauty there glowing from the inside and displayed by the outside? How can I not see what everyone else obviously sees?

I remember when I was a young teen dealing with acne and self-esteem issues and asking my dad if I would ever be anything more. He looked at me then and told me to wait until I was 18 because I would blossom into a beautiful young woman. At the time, I thought he meant wait until the acne stages are over, and by 18, guys would find me desirable and attractive.

So needless to say when I turned 18, I was disappointed. I wasn’t pretty. I was 10 pounds heavier because I had taken steps to overcome my body image issues and stop starving myself. And I wasn’t getting any attention from guys. But I also had one of the best body images of my life. I truly was happy with myself, even if I wasn’t happy with life. I knew who I was, and I loved who I was, but I wasn’t sure the world did.

That led down a negative spiral. I hit the worst depression of my life by the time I turned 19, and I lost ten pounds because I stopped eating. And this was all before diabetes came along. Believe me that played its own part in my body image issues.

But now here I am, 28, and trying to date. Because I still don’t get attention from guys, I’ve learned to be proactive. This has made me stronger and more confident. I know what I want, but I also know who I am now, and I’m okay with that. I’m not going to pretend to be someone else for the sake of a guy’s attention. After two back-to-back dead-end relationships, I’m not going to bullshit anymore. And if that means I end up alone, I’m okay with that, too.

After growing up perpetually single, it’s kind of what I expected. I’m not saying I’m not open to the idea. We all need companionship, and there are definitely aspects of being in a relationship that I miss. But I’m not waiting around for Prince Charming. I’m moving on with my life, and I’m going to make the most of it.

I always have (and to be honest, the guys I’ve had in my life have always dragged me down). I don’t need that, and if I find someone who can be equal to my adventures, then I know I will have found that companionship. But until then, I will try to be more observant and confident in myself.

I don’t know if I will ever consider myself “pretty.” And maybe that will keep me from being vain? But I have no problem calling myself “confident.” As a woman in today’s world, I’d rather be confident than pretty anyway.