Changing the Rules
Too Old to Feel This Shy
Of course there are things you can do. First of all, take a good look at the women the men you know are dating, and then take a long look in your mirror. If guys are going to take you seriously as a desirable female, it helps to look like one. You don't have to start dressing like a two-bit hooker, but changing your hair and putting on a little makeup can have a startling effect on the opposite sex. So can a pair of high heels and a flirty little dress, but even in jeans a girl who wants male attention should be paying attention to her looks. Yes, I know, a really great guy should be interested in more than your surface, but unless he likes what he sees, you may never get the chance to show him what a brilliant conversationalist you are. Never underestimate the value of sex appeal. That's why they call it that.
As for this particular guy, well, there is no fail-safe way to change the rules, but you can minimize the risks. Any time you know you're going to run into him, be sure you look especially good. Without overtly flirting, try to steer the conversation to an area you're both interested in, which, if he doesn't pick up the hint, could give you an opening to invite him to join you, ever so casually of course, for a movie you both want to see, a bookstore you want to visit, a restaurant you've both been wanting to try, or a sporting event--you know him, you should know what he likes.
Then, when you're alone, if you dare, you can be more flirtatious. If he responds in kind, you're on your way. If he gets this weird look on his face like you're starting to creep him out, tell him there's this guy he never met way across town that you've sort of got a crush on and you were just trying out your technique on a pal before using it on the new guy. Or tell him you never realized how cute he really is and it just made you want to flirt with him. Or go out and get a copy of Seventeen magazine and get some advice from someone who really knows about this stuff.
I already know the answer to the question I'm about to ask you. It's just that doing what I know is the right thing is hard. I'm 21 years old and living with a man I've been with for almost six years. He proposed last year and I accepted without thinking. He bought me a house and we've been living here ever since. The problem is, I no longer want to marry him. He's six years older than I am, so he'd already experienced much more of life than I had when we met, and now I realize I want to create my own experiences. I still love him, but I think it's because he has always taken care of me. Even before we lived together he was there in the background to help out whenever I asked. But I feel like I'm grown up now and no longer need him to take care of me. I know I need to let him move on and I've already given him back his ring, but I'm very comfortable here and life is so much easier. I'm not good with money, and I'm afraid of what might happen if I venture out on my own again, because I'm so used to his support. I'm also doing really well in school for the first time and I'm afraid if I leave him I'll flunk out. How can I move forward and let him go?
Scared, Stuck, and Feeling Stupid
I can accept that you're scared and feel stuck, but you're not stupid. You're smart enough to know that marrying the guy would be an easy answer to some of your problems, but that it probably wouldn't make either of you happy for long. You may always thank him for his love and kindness, but a debt of gratitude is no basis for a marriage. Leaving home is scary for just about everyone, and since you were so young (technically jailbait) when you met this guy, he's become as much a parent figure to you as a boyfriend. If he's as decent a guy as he sounds, maybe he'll let you set a deadline, perhaps the end of the school year, that would give you a chance to throw open a window on your independence, so to speak, without immediately having to hurl yourself through it.
In the meantime, at the library you can browse through enough books on finance to learn how to balance a checkbook. Get a part-time job and start saving. As the time for moving out gets closer, start looking for a good roommate situation. When your goal is clear, it's surprising how gratifying taking even baby steps toward it can be.
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