To my little (not so little) brother,
Its nearing that time in your life when you and your friends will start having girlfriends, and the first one is always the hardest because you really don't know what to do. Not that I'm an expert on relationships, but I have learned a lot from my past relationships and, as your older sister, I want to give you some advice on the way you should treat a girl.
First and foremost, you have to realize and acknowledge that you do not need to be in a relationship to be happy. Being in a relationship will not automatically solve your problems, and it will not necessarily make you happy. And when you are in a relationship, you shouldn’t let your happiness rest in her. People come and go and you can't let your happiness depend on someone who may not be around forever. You don't have to be in a relationship just because "all of your friends" are in one.
Make sure you really like her before you ask her out. When you are younger, its easy to confuse being close to someone and having feelings for them, but you'll feel something a little bit different in your heart when you have true feelings for her. Don't let yourself feel pressured by other people to ask her out, make sure it is really what you want to do before you do it. But if you choose to, you don't need some grandiose gesture to ask her to be your girlfriend: simplicity works best. Most girls don't like over-the-top gestures.
Talk to her. One of the most important things in any relationship is communication. Make sure you learn things about her, and don't just ask her questions and pay no attention to her answers. Listen and remember even the little things she says, it'll make her smile when sometime down the road you bring up a little detail about her. Find out her likes and dislikes, find out what she's afraid of, who her best friends are, or what her pet's name is. And make sure you tell her things in return. She'll want to know just as much about you as you want to know about her.
Remember to do the little things. Little things are so underestimated in a relationship. You don't have to go out of your way to talk to her from the time you wake up to the time you go to sleep, but little meaningful texts throughout the day will remind her that you're thinking about her. Text her good morning when you wake up, and good night when you go to sleep. Ask her how her day was, and then ask her what happened that made her day bad, or what happened that made it good.
Mean what you say when you say it. Don't say what you think she wants you to say, say things that are your true feelings. Love. The L-word is a very strong word, and this goes back to meaning what you say when you say it. Don't just say it because you are in a relationship and you feel like you should. When you tell her you love her, make sure you really, really, really, really, really mean that. If you guys break up, she will question everyday for a long time if you actually loved her when you said you did, or if was all for show.
Be a gentleman at all times in the relationship, from the very beginning to the very end. Make sure you don't say things out of anger that you will regret the next day because those are the things she is going to remember the most. If the end of your relationship comes, make sure you treat her with the same respect that she deserves. If you break up, absolutely do not drag her name through the mud, do not leave her in a parking lot, do not go around telling people she is crazy or un-dateable, and do not tell people the secrets she confided in you. She may not be your favorite person post-breakup, but you still need to act mature around her. Immaturity proves you were not ready for a relationship in the first place.
Always remember that, no matter what, you can come to me with any questions or if you need advice. I'm always here for you, if you need to talk to someone to figure out if she's the right girl to ask out, how to ask her out, or a shoulder to cry on if you need it. I want you to think of me the way that Ross thinks of Monica:
