Should I go for it?

Hey there, look I totally understand how you feel, but I don't think you are bad person for not liking your homecoming date, although from where I see it, you either went with him to the dance because you wanted to go but not alone, or you wanted to see if maybe spending some time with him In that context could actually help you see if maybe there could be something between you, but obviously there isn't, so ...I suggest you break it off with him, and stop giving him false hope, or going out with him out of pity, cause that's worse for both of you, even more hurtful. But don't feel bad for not liking someone, sometimes there is just no chemistry, now, make sure you are certain you don't feel anything for him and the reason you're being like this is not because you're hooked on the other guy, always thinking about him, wishing your "ex crush" (which, not so much of an ex, huh?) was the one dancing with you and not your present date. What I'm saying is, be fair, and be honest with yourself, and the other boys and don't let too much time pass by, with either of them. I hope this was helpful, and wish you the best Let us know, how it goes.

"I gave him a chance, but honestly I am not interested"
??????????????????????????????
"I don't know how to break it to him"????????????????????????????????????????????????????
Maybe you should talk to him directly and let him know that you don't feel the same way that he does?Instead of sending indirect, confusing signs that you just hope he'd comprehend and read your mind.Telling him that you don't like anyone is a confusing sign. He might take that as an opportunity.And you even know that you have to SPELL IT OUT for him, and you still acted this way
This is what I hate about girls the most, accepting requests, wasting the guy's time, just to give "signs" that they're not interested when one simple text saying I'm not interested would have sealed the deal. What's there to gain out of this?Please change your approach on how you handle relationshipsGo and talk to the damn kid, he thinks the world of you.Let him know how you truly feel and end this misery for him.Stop listening to your friends, you and they don't know any better.You say you like to beat around the bush because you don't like making people sad,but what you're doing right now will make it even worse. It's easier not to be sad when a manhas direct answers.

in this case, I think you're ok. you didn't do anything really bad, and yeah he will be sad, but it's in his character to do so. He'll have more heartbreaks in the future and they will be just as painful so long as he's clingy. I think everything you did was reasonable, and yeah, you gave him a chance, but you really weren't interested. You made no promises, this is not like nosilla's thread about breaking up with her fiance over another guy. that one is bullsh*x, but you did alright, you're not even official with anyone. I also understand you being tired of constantly having to keep distance and gave up at the end, and he prob even got his hopes up because of that. but you can't do anything about it, it's ok, maybe not for him, but just worry about yourself for now. the problem is not too big to fix. and why don't you just go after your crush anyway, I don't think it's "previous crush", I think it's "still crush".

You need to give the guy his respect and tell him directly that you're not interested. If you tell him what's up, he will be sad. If you beat around the bush, he will be even MORE sad when he finds out. Giving signs and beating around the bush is wasting both you and his time AND making it worse in the end.

You haven't done anything wrong though, no one is a bad person for not returning someone's feelings lol. It's not something you can control. However telling him that you're not interested is something you can control

If you're gonna do it, do it right, right, do it with me!

That's what George Michael would have said, and he did. Back in the eighty's.
He was right back then, and he's still right now damnit!

Get to it, don't postpone, take me to the edge of heaven, one last time might be forever.
Another George Michael quote, the man possesses infinite wisdom!
Take notes please!  

"...doesn't get the message unless you SPELL IT OUT FOR HIM. I'm the kind who beats around the bush (because I hate making people sad),..."

Just these two lines basically sums up your drama. You don't like being straight and he doesn't get it unless someone is straight with him.

Worst of all you're not even actually dating him! Just bloody tell him to his face.

This isn't going to end well unless you sort this out. You might think tbe burden is on you and in this case it is because the ball is in your court. He played his shot and is now waiting for you to reply. Instead of being all wishy washy just get it done.

High school. .. where people learn all the bad habits that screw their relationships for years to come

Jeezus christ, you are fickle.

You knew about his emotions before the homecoming event and just threw out the suggestion that you didn't mind going with him? Because given your knowledge of his clingy nature, you obviously didn't understand that he would take that as an opportunity, if not sign, that you were interested? Worse so, you still haven't made things clear with him?

You have the inside knowledge of both your and his emotional interest, and you know it's not going to end well for him. Do you really think delaying that point is to his benefit or is it perhaps you just don't want to deal with emotional fallout that you took a part in creating?

You need to tell him straight up, make sure he understands, then you need to sit down and really think about what happened and how it reached that point.

It's funny how girls try hard not to hurt guys' feelings but end up hurting them more in the end.

That's exactly what's happening here.

Beware of karma, OP. One of these days there'll be a guy who you'll be crazy over and kinda gives the impression he likes you but doesn't make it overt and doesn't come right out and say it but at the height of your feelings for him he'll either tell you he's not interested or suddenly begin dating someone else.

Your first mistake is "giving him a chance" you shouldn't force yourself to give chances because of guilt. Guilt and unsincerty eventually catches up and is were you are now. The only way to fix it is to talk to him and settle your feeling knowing that he understands that you merely want to be friends. Its okay to ask your crush after clearing it with your friend if you want a clear conscious. Then he has to respect your choice. He will get hurt but its better now then to drag it out. Like you said he easily falls out of love.. gives him his space and he'll move on. Good luck! ♡

pity does not equal to lovepick a day, and ask him to meet up for coffe or something then tell himtruth hurts but lies hurt even morepretense does not benefit for both side of the party
Id learned it all from my past datebe honest, be frank. no games good luck!

Just be honest. No guy likes to be strung along