You don't need to be pretty, because you are beautiful. Despite what you may think, those guys that you like might be looking for a girl just like you. The assumptions you are making about the girls these boys like is based off of social stereotyping. Self-confidence is the sexiest thing you can have Dates can be anything you want! There is no reason why a dinner out should be considered more or less of a date than going to Walmart and having nerf sword fights (my personal favourite). If there is something you enjoy doing, or a place you like being, that can be your jumping off point for a date. Clothing should be what makes you feel happy, while still begin practical. There is nothing wrong with dressing up, but just remember that you don't want to create a false image, so be true to who you are. Try slightly dressing up what you would normally wear, there is no need to do a complete makeover. If in doubt, have a fallback outfit that makes you look and feel amazing. I highly recommend polka dot dresses! Before you go setting the ground rules for your date, make sure you have a solid idea of them yourself. Write it out if you need to, just make sure you know what they are. Looking for someone within the same faith might be helpful in this case? Ultimately being forthright with your values and rules is something you should not be afraid or ashamed to do. If he respects them, then you are on the right track I'm not sure what your personal stance is on online dating, but from personal experience, it can be beneficial, even if it helps build up your confidence. My best friend met her fiancé online, and they have been together now for almost 3 years. I'll end my little blurb with something my professor told me on a really bad day. "You are an intelligent, attractive young woman and your potential is only limited to your will to succeed." (I keep this stuck to my mirror, it might annoy me sometimes, but I know it is true!)