Dating can be a lot of things. Fun, awkward,refreshing, sexy. It is all new territory and it can be an absolute blast.The concept of dating isn’t for everyone however, especially if you tend to be an introvert or don’t have a lot of experience approaching women. Even men with confidence to spare still struggle when pursuing a woman they are excited about. Once you’ve met someone you want to date, the thought of asking them out can be intimidating! It may not be easy at times, but having the right tools can really change the game. That being said…
Do be prepared for a first date. There’s nothing better than a man with a plan. If you’re going to ask a woman on a date, be aware of your schedule and budget first. If you can’t afford to take her to an expensive restaurant, be prepared with a place you would like to take her instead. It’s important to know ahead of time when you are free before you ask her if she is. Knowing all of the details before you ask her out is a great way to show attention to detail, which is always a huge plus. 
Don’t compliment a woman if it isn’t genuine. Paying a woman a compliment is a great way to start a conversation, but make sure the compliment is real. Don’t tell a woman she has a beautiful smile if her eyes are really what caught your attention. Be confident in what you like about her. Did her laugh make you smile? Tell her. Do you think her shoes are cute? Tell her! It starts the conversation off honestly, and will make her remember you. 
Do insist on paying for the first date. Don’t offer. Insist. One of the easiest things you can do to impress a woman is to treat her. A great rule of thumb to follow? If you asked her on the date, pay. If she reaches for her wallet, she is probably hoping you’ll reach for yours. It’s polite and also provides a comfort to a sometimes awkward first date. 
Do make eye contact. This is huge. Whatever you choose to say, whether it is a joke or a question, say it confidently. Having confidence in what you do or say is important, especially when you’re wanting to make a good impression on a woman. The best part about confidence, is that it’s always attractive. That being said, remember the difference between confident and cocky.