Oh, don't you just hate when that happens?! My school is small enough that there are like 4 or 5 "squares" and then all those squares join together in the corners xD

Okay, first thing is, I don't know how old you are, but generally I recommend staying out of the whole "crushing" thing. I have a really strong belief when it comes to dating, and the fundamental of that is, don't date and avoid crushes until you are much older. Although "crushing" can be inevitable, I know. Just don't worry about it. Trust me, I have seen enough kids throw away their entire lives in heartbreak, throwing away all their goals, failing school, some even dropping out. I would hate for that to happen to you.

Now, if you insist, then... go with your heart. I mean, if you do wish to go after anyone you like, there is a good chance of upsetting people. It's a risk, so it is up to you whether or not it is worth it.

As for your friendship with Jake, just let things smooth out on their own. He'll lose interest, maybe a bit heartbroken, and come wondering back. That's the danger of love and crushes, it changes people forever. But not to scare you or anything, I am just speaking from what I know. Also, have you considered talking to him about how you feel your friendship may be fading? Maybe Jake will realize and work to fix it.

Oh, and on your last part? DEFINENTLY don't try to make Jenna like him. Trust me, this will get you in the hardest thing ever. Jenna will figure out and hate you, Jake will probably get angry, you'll be ashamed, lose real friends, and anyways, you cannot play matchmaker. It doesn't work that way.

The way I know all that? Let's just say, coming from a high school, 90% of people are obsessed with dating, and I know a few who tried to play matchmaker. I saw what happened to them and all their friendships, it wasn't pretty.

So first choose what is worth the risk. My recommendation? Don't meddle in crushing or matchmaking. Just talk to your friend, but don't push Jake in any way. He will get over his crush as most everyone does. Just give it a bit of time. Just stay strong!  

As always, Ashlee has wise advice. You don't need to try to get Jenna to like Jake. This is a messy situation. but if all you want is to avoid hurting your friends, then you're going to be just fine. It's out of your control that Mike likes you, so Jenna really has no reason to be upset with you.  Just try to be a friend to everyone and be honest. If you want to, then let Jake know that you miss him and want him to treat you like a friend again. Whatever happens, you'll be okay if you know you tried to do the right thing.