This is a question where one would have to look deep inside of themselves in order to answer. First off, if the person was ugly and deemed not to be attractive, is that your preference. If you know what the person looks like and if they are so called ugly, do you accept it. This is all about a question of why you would be into the other person. Do you like them for their looks or do you like them for what they stand for and how they feel inside.
I would not have the frame of mind to think that way when I was looking to date. I would be looking for what they have in their heart. For that reason then yes I would say that it would be a good thing to date someone that is uglier than you. They could be a very good person on the inside and could possibly give you more satisfaction in a relationship than someone who was prettier than you.
Before asking a girl out for a date, you may want to talk to her first. You should have some conversations with her by text, email or phone. This will not seem so awkward when you ask her out for a date. If you had never spoken to a girl before asking her out for a date, it may seem awkward to ask a girl out for a date without really knowing her. She would probably look at you strange. Instead, get to know her first.
Talk to her about her likes and dislikes. Also, you will want to tell her things about you. Then after a while, you could text or ask her to go to a small date like getting a cup of coffee or a meal at a nice restaurant.