To the Guy About to Ask Out My Best Friend

You’re taking a big risk buddy, but congratulations.

You have reached the point in your life where you would like to ask out a girl. Trouble is, this girl is my best friend.

That is a big step, and rather risky waters. I amend you though. Here is my advice.

1. Don’t over think — Girls are complicated species. We have weird feeling and are usually quite delicate and emotional. That being said, one of our signature feelings is embarrassment. Most girls do not know how to express this correctly, so they hide or run away. The girl might really like you, but they do not know how to show it. If you ask her out and she likes you, but she doesn’t expect you to ask her out, she might act a little weird. This is normal, and in most cases, they will come around to their senses once they get themselves under control. But you have done nothing wrong. The second part of this point is that you do not have to find some elaborate way to ask her out. The impact will be just the same. You do not have to go all Flinn Ryder (from Tangled) and come riding in on horseback to get the girl. A simple hand picked bunch of flowers and movie session will do just the same impact.
2. Take It Slow — Alright, so assuming that she does feel the same way about you, and you do end up going on your first date, don’t push things too quickly. Something else about girls is there is really two types of us. The ones who literally talk FOREVER, and the ones who sometimes have trouble thinking of things to say. That being said, I suggest you play it out like chess. You are the white pieces, so you make the first move. From there, let her go. If you follow this, if she is one to be more on the quiet side, things are bound to flow nicely.
3. Getting to Know Her — Movies and softball are not the only things to talk about. I suggest you do some research of other things to talk about. Sure, that is all that you guys might have talked about so far and sure they are great things to begin a conversation with, but if you want to someday be with her, you have to talk about more. Which moves me to my next point…
4. Boyfriend/Girlfriend — I suppose this could go into the category of taking it slow, but it’s not. Being “together” does not necessarily need to have a title go along with it. Sure some people like that Facebook official status where the whole world knows that you two are madly in love, but it does not have to happen immediately. I get that you like her, I do and maybe she feels the exact same way, but who is to say that after you guys go one dates together and begin classes once again that things won’t get crazy and you won’t even have time for each other? There is no way of knowing that right now, so why jump into titles so quickly? Anyways, if two people are meant for each other, everything will fall into place.
5. You Hurt Her, I Hurt You — Okay, so it is inevitable that there is that one friend. That friend who gets both sides. For some reason I am that friend and I will always be there to give advice on both sides, but just know, if things get ugly and it’s your fault, I will ALWAYS take her side. She is my best friend anyways. I will support your relationship and whatever, but do not be that person. I know college is the place to really find the people that you love and maybe your relationship will work out, but also maybe it won’t. I will not be mad at you and I will be a shoulder to vent on if in the end she breaks your heart, but if you break her heart, unless it is a really good reason, you better be ready for me to smash your face in because I will defend and fight for her if you screw up and break her heart over something stupid.

Now, all that being said, I am rooting for you guys and I do hope for the best.