12. Kat Dennings
This is a bit of an odd one, as while he was able to have his cake, it doesn’t seem like Drake was able to eat it, too. The way he tells it, he was more of a fan looking to get dinner with his crush, and she was kind enough to oblige him. It was just the one night out together, and he claims that she never called him back afterwards. It seems fairly rare for Drake to see a girl just one time and then never again, so Kat is in a small minority. Most of his old dates can be connected to him again even years later!
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