I've been wondering this for a while.

Often when I'm trying to take seddit's advice, I say something that is clearly cocky, but I say it with a smile and a look that makes it seem like I'm joking. Is this a good strategy? I'll give you an example:

me: 'i'll be gone until friday, sorta sucks but ill live'

her: 'oh thats not too bad, it goes by slowly though because i have nothing to do nowadays'

me: 'you need to find something to do other than hang out with me, i know everything else pales in comparison but you have to try' (with a smile)

or even something like:

me: 'i have to go to xxx to meet my friend (xxx is a place known for being full of unattractive people"

her: 'no dont go, there aren't gonna be any attractive people there'

me: 'woah woah hold on a second'

her: jokingly 'oh, sorry, you're attractive, i meant other than you' (important to note that this is said in a laughing joking tone)

me: 'i think by attractive you meant to say smoldering hot' (with a joking tone/smile).

I don't think those the best examples ever but it's the only ones I could think of right now. Basically, I'll say something that is definitely cocky, either about my looks, my charm, my intelligence etc, and it won't really have subtlety or anything (like the only meaning of what i say is a compliment to myself, at the end of the day I'm saying "I'm smart" "I'm attractive" "I'm cool" etc), but with a smile that makes it seem like I'm joking.

I originally thought this is a pretty good strategy because its playful, but I don't know. On the one hand its playful, but on the other the girl either takes it at face value, which means I'm arrogant/cocky in a bad way, or takes it as a joke, which could make her think I'm not confident since I basically say "I'm attractive" or "I'm cool" or whatever as a joke, i.e i dont really think I am.

What do you guys think?

[EDIT] Just remembered a good example:

her: 'i have plenty of other things to do lists some stuff'

me: 'makes a joke about some of the stuff. and besides, you know hanging out with me is better than any of those things' (big smile)