Stop convicing him then. When he calls and says "I dont know if I'm gonna make it" just say "Okay, maybe next time!" and hang up. He'll quickly learn that you arent interested in coaxing him anymore and he'll either stop coming and having fun at these events or he'll suck it up and keep coming but stop calling.

"Don't fall for someone who's not willing to catch you"

sounds like someone wants to be invited as "the special guest"

Why don't you just tell him exactly that - you've noticed the pattern and you think it's rather pathetic. So either cut it out or don't bother coming at all.

I don't think this really conflicts with the cocky 'tude. This is someone who's under the impression that he's super special and people ought to make extra effort if they want him to do stuff.

I agree with sundaygreen, just tell him straight-up that this behavior bugs you.

I think you've got it backwards. Sometimes the guys that seem the cockiest are the most insecure. A lot of the most attractive, cocky guys I know are the most insecure. It is frustrating. I would just tell him the truth. If you're nice about it, I don't think he'll be offended. He may not realize that he does that so often.

I agree with pixiedust, the cocky guys are usually the most insecure. Tell your friend that if he's really a friend he needs to stop playing these headgames with you. If he still does it after that or gets pissed off, STOP INVITING HIM. End of story.

I agree with pixiedust and sporky, the guy is really, really insecure. If you decide to invite him again, you can add other people enjoyed talking to him or something else, that doesn't come off as begging. If he still continues to call for reassurance, then tell him you're busy getting ready for the party and you'll see him there. It's not on you to change or take responsibility for his insecurity. You're not his mother or therapist.

Call his bluff. Once he's invited, let that be it, and ignore the whiny messages if he keeps calling. Let him know he's wanted, but don't play along with his mind games, because they are silly and exhausting.

Yep, pixiedust is right - cocky guys are usually compensating for insecurity. Maybe at the last minute he thinks, oh, what if she didn't really want me to come? I honestly can't think of a single guy I've known, friend or romantic interest, that didn't have some kind of quirky attention/affirmation-getting habit like this. Maybe understanding why he does it will make it less annoying, but you could also gently and teasingly say next time he calls, "Oh good, I was WAITING for this phone call, you're not coming, right?" then when he says WHAAAT??? Just laugh and say, "Well you're always so indecisive at the last minute, but you know we want you to come, right? So you BETTER be here in 10 with a bottle of zin!!!" Gentle teasing is usually the best way to call attention to something annoying a guy is doing.

I can see that this would be super annoying, but is it really that big of a deal? It doesn't sound like you have to go out of your way to make plans for him to come (like picking him up or making other special arrangements because he's promised to come), so he's not ruining your plans or your events by doing this (even though, again, it does sound super annoying). I think jacrabbit84 has the right idea with the gentle teasing.

It sounds to me like what you're taking issue with is his "cocky" attitude, since you use that word a couple of times in your post. And that's a whole different issue.

I'm with Fallen. Next time I'd just be like, "oh, too bad. sorry i can't chat, it's quite busy over here. bye!"

tell him straight up. stop being a baby and make a decision on your own. I invited you because I want you to come. what more do you want?

I dont get why this is even an issue. Does the party stop if he doesn't show?

If this friend is obsessively calling when you don't pick up and making you beg for him to show up places, then he's got some issues. He wants you to feed his ego by saying you need him there. Don't do it. Next time, just say "Okay. Do whatever you want" and leave it at that. You shouldn't have to constantly reassure him.

When you invite him, say "Hey, there's a party at my place on Saturday night. It'd be fun if you come, but you always tell me that you're busy, so if you can't make it, don't worry about it. You don't have to call again to let me know." If he calls you anyway to say he can't come, don't be afraid to sound a bit annoyed and say, "I know. I already told you it's OK and you don't have to call."

Protect your heart until you find someone who can do it better than you.

Just call him on it. He's probably not aware that you've noticed. You're right about his reasoning too.

I have a male friend that does the exact same thing and I think it has to do with both insecurity and his ego. Recently I asked him if he could bring me to the hospital for a surgery I had scheduled and he said yes and then leading up to the week before the surgery kept going back and forth of whether he could do it or not. I ended up deciding to ask someone else because I didn't need the stress of wondering if he would follow through or not and I haven't talked to my friend much since. I agree with calling your friend out on it and or to stop inviting him out to do things.