Q: Why can't I meet a girl who is confident about herself and has a great smile, someone who is fun, assertive, daring, likes to have a little adventure, a girl with a great laugh, a caring personality?

A: That girl is out there and you might have already met her. You need to be certain that you are projecting these qualities that you're looking for.
Are you confident in your expression of yourself to new people you meet? Are you fun, assertive, even a bit daring? Something tells me that you are adventuresome, laugh a lot, and have a caring personality. So you simply need to express what you want, and she may even find you.

Q: I know there is no reason for an assertive woman to feel less attractive, lacking in empathy, or not be very likeable. There is no reason why a woman can't feel assertively feminine, but a small voice, maybe from childhood, is always telling me to tone my naturally assertive nature down a bit. Should I listen?

A: First you need to look and analyze before you listen. If you and others are seeing an assertively feminine woman truly, and perhaps only your best friends will level with you on this, then you can follow your natural assertive manner.
But, if the feedback from yourself, after some careful examination, and others indicates you are too demanding or worse abrasive in your interactions with others, then you might pay some heed to that small voice.

Q: I've tried to be more assertive for years, but I still feel bitter at times that others often use me or walk over me. I know this deprives me of what I need and deserve, but I don't know what else to do.

A: You may need to make a plan, get books for guidance or talk to a professional about learning to express yourself more assertively and more effectively.
This sometimes takes a good deal of work to build self-esteem and self-confidence, keys to being more assertive. There are examples of famous people such as actress Jane Fonda, who said it took her years to become more assertive and get over the "disease to please."
Don't berate or demean yourself for what's past, but move forward with steps to tell people your desires and needs in a politely assertive, but firm manner. Then, others will respect your wishes and be more accommodating. There are books listed on this blog which could offer a helpful start for your plan.

Q: I know I'm not as assertive as I should be. I wonder how much a weak self-image or lacking confidence is the root cause?

A: Everyone down deep lacks confidence at times from presidents to professors to high-wire walkers. There is an old saying:
"never let them see you sweat."

Maybe you need to learn to be more assertive by taking an inventory of your self-image. List the areas where you have strengths and have had successes, and also note where your life plan needs work.

This can be a good jump start on more self-confidence and self-esteem. If you don't feel you're making progress in a reasonable time, it is possible talking to a professional would be beneficial.