Kayla, Isha's advise is spot on here and others are good as well. You say that your girlfriend is the reason you started dressing again, so I am assuming that she knows and sees you when you are dressed. If you are concerned at how you look, ask her for help or her opinion, if she knows i'll bet she will be willing to help. Also If you would like some help with your look, consider posting some pix of you dressed in different outfits and make-up. The girls here would be happy to critique your look for you.

From what I can see in your profile picture you have a lot going for you, most importantly is your youth. I think you would probably blend quite well. Their are a lot of tricks with make-up that can be used to draw attention away from male features and to highlight the feminine ones, YouTube is full of tutorials in this area. Going to cosmetic counter at a major department store or a Mac or other specialty cosmetic store for a make over is also a possibility, I have found them to be very helpful and also very friendly to the TG community. Other little things like trimming your eye brows a little to neaten them up, can greatly improve your look, they do not have to be overtly feminine to improve your look but bushy eyebrows scream guy.

I can sympathize with your dilemma over your desire to be "passable enough". For any of us who are out and about it is something that we all struggle with. Keep in mind though that we are our own worst critics and can easily see in our selves the familiar features that no amount of make-up can hide from us. It is a different story though when others look at us who do not know us, they are not looking to see if we are the same person we were without the make up, they only see what they see. I know that I am not "passable" when I look in the mirror, but when I go out in public feeling relaxed and confident in who I am, I rarely get a second look. My wife is always looking for other peoples reactions when we go out together and is amazed at how often people either do not care or do not notice and just go about their business without a second glance.

The most important thing I have found in being out in the main stream world, is to be comfortable and confident in who you are. If you are nervous or trying to hide your self it will only draw more attention to you rather than away from you. People notice when someone is nervous or not comfortable with them selves and will usually look harder to figure out why. So when you are ready to make that first trip out the door, be confident and own it, you will be amazed at how great it feels.

Good Luck
Michelle