I like both but the Clinique ones may have a more glossy-full mouthed appearance and finish to them that will transfer more. The Tarte lip stains are slightly more pigmented and will stay on the lips longer.
I haven't used the Tarte product so I can't comment there. The Chubby Stick is nice but will transfer color and the Philosophy gloss will make a mess. I used to love the Philosophy glosses but I think they changed the formula and now I find them to be way too thick and sticky. If you want to know the truth about kissability-most guys hate sticky gooey lips. You are much better off making sure your lips are soft and in good condition by using a lip scrub and lip balm in the evening. When you know your going to be kissing, I would suggest softly blotting whatever gloss you have on so he can make contact with your lips and not the gloss. Have fun!
There's about 3 threads on this by now, I hate to sound witchy at all, but, are you near a Sephora or Sephora JCP or any other cosmetiic shop with these in it? I highly recommend swatching these or getting samples! That will be the best way to know which will suit you best. Although the least transfer will be from the chubby stick or lipsurgence, I haven't used either personally, but I hear that the Clinique gets fantastic reviews (although I haven't been impressed by very much from them) and I haven't disliked anything I've gotten from Tarte. Hope this helps on your search!