To the guy my sister dates,

You are the luckiest man alive. (Maybe the second luckiest, after all the guy that I choose to date will be luckier.) If you don’t realize that, you should just move on now before my sister gets more invested in you. There are some things you need to know before you date her.

She is absolutely amazing. She will throw harsh and critical comments your way, but it’s only because she loves you. If she’s not mean to you, she doesn’t like you. My sister is full of sass and is hilarious. I wouldn’t change a thing about her and you shouldn’t try to either.

Some things to keep in mind if you date my sister:

1. You must agree to treat her like the princess she is. Always be nice to her, except when you’re joking around, but be careful not to take it too far.
2. Remember: Me vs. you. I can criticize her and talk badly about her all I want. You can’t. I can be mean to her. You can’t.
3. I love her and if she loves you I will accept you once you’ve proven to me I should. If you give me any reason to doubt your love for her or your character, I will write you off so fast you won’t know what happened. Don’t worry though, I will make it very clear that I am unhappy with you dating my sister and will tell both of you exactly why. If you work it out and prove to her that I am wrong, I will sit down and let you continue as you were before, but will hold some reservations about you. I don’t trust people easily and I definitely won’t entrust my little sister’s heart with just anyone.
4. This brings me to my next point, what will happen if you hurt my sister? Good question! You will be written off, I will probably yell at you after she does or send you a very passive aggressive text with the intent of making you feel extremely guilty or scared. Depending on what you do, I/we may or may not show up at your house to have a little chat. My entire family will turn against you and that’s a lot of people who hate you. We will most likely already think you aren’t worthy of her, because that’s just how we roll. Basically, don’t hurt her or I will make sure that you deeply regret your mistakes. If you have further questions about how I would do that, feel free to ask, I would be more than happy to tell you in person. However, if you aren’t planning on hurting her then there’s really no reason to ask, right?

Now that you know a little more about what I expect of you and what will happen if you hurt my best friend, we can talk about what you can expect if you turn out to be good for her. This means you make my sister happy, inspire her to be a better person, and make her feel special, which is exactly what I, and hopefully you, want for her. With my seal of approval, you will be welcomed into the family in my eyes (whether you really want to join our crazy family or not, I don’t know. I love them and hope you will too.) This means I will joke with you just as much or maybe more than she will. I will text you about her when she’s in a bad mood to see what happened so I can start to fix it. I will warn you when she’s in a bad mood and give you tips on what to do, help you get out of situations, figure out presents for her if you need help, and be a sounding board for anything involving her. We can keep each other in the loop about her life, when one of us is with her and the other isn’t. It’s quite possible that I will end up awkwardly third-wheeling one of your dates at some point. Sorry about that in advance. Also, fair warning both my sister and I will probably try to make you feel awkward sometimes. I’m not sure why we do that, but we do. My best advice would be to just roll with it and laugh it off and if you really want us to stop, it’s totally fine to tell us.

Once again, if you decide to hurt her, I will consider it a formal death wish.

We are a package deal and dating my sister means putting up with me too. I’m a fun person (I promise) so long as you don’t engage protective sister mode. If you’ve made it to the end of this, I’m going to assume you are truly interested in dating my sister and to that you should know that she will be the best thing that has ever happened to you.

Good luck getting past me first.

Sincerely,

The Older Sister