Thank you for these great logos! Here's some feedback which might help clarify what I'm looking for.
Entry #1 - I like the font, simplicity, and splash of hot pink color. It took me too long to figure out the K was the stem of a flower w the petals ripped off. I like that this logo translates well to small sizes for twitter and Facebook. I think it would be easily readable even if it's a thumbnail size which is important.
I think if we were to go with the "he loves me, he loves me not" concept, the flower would have to be separate from "Kate's Dates" and "he loves me.." would have to be incorporated into the logo in a much smaller font.
Entry #2 - love the concept with all the guys hiding behind the letters. My concern is that it's too busy and the "Kate's" portion of the logo is not going to be readable at smaller sizes.