Don't underestimate the competition, although you have the advantage because you actually know about her. Even if you run out of things to talk about, the awkward silence will disappear quicker than you know it. I hope you win her over! You will know when he comes into your life, no questions asked. Be honest. I appreciate how [punctual/thoughtful/kind/generous, etc.] you are. You've just told a joke, she's laughed her head off... or Wow, what's a guy like you doing in a place like this. The hard part is deciding which one is for you. Good questions include: What's your favorite hobby/color/sport/etc.?. If the girl seriously doesn't like you after this, just wait. Can dating websites I blink? Boxes containing hand-picked personal yet useful items are great, such as bath products or sports related items like a drinking bottle, that can be used daily by your loved ones to ensure they are always thinking of you. If you're into underwater basket weaving, and he's taking a class on submarine repair welding, casually ask what kind of wetsuit he prefers, or if he's ever had trouble with his oxygen tank. You'd be surprised how often dates turn up without showering. We've all heard what bad karma it is to take away someone's man. Enjoy your single status for a while. Pick your clothes early. Humor is what helps to reduce the whole awkwardness of dating and it also lets both of you know that you're humble and not full of yourself. Yuse spel chek. If he doesn't, you could risk getting dumped. Do actually date. If your school has a strict uniform policy, try to spice it up by adding a cute belt to your pants and by adding jewellery. Try to keep it short and simple. Women are looking for (in order): Personality, sense of humor, common interests, intelligence, cleanliness, looks, sexiness, getting to know the man through a friend, voice, spirituality, profession, money, talent, and finally, religion. Being funny is innate, provided you trust your sense of humor to shine through. Plus, the ones with big memberships can overwhelm you numbers.