Since Shri Krishna is BEYOND THE SENSES, INTELLECT & IMAGINATION OF ONE & ALL, there is no one who can know Shri Krishna as he really is, there is no way anyone would ever get to know what Veds mean by "Anant Anand (infinite bliss) for no one is capable of experiencing that bliss, only Shri Krishna actually knows who He is.
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So being infinitely benevolent, what Shri Krishna does is that He always appears not as ONE, but Two, that is He takes another form & since that other form is still Shri Krishna himself, this other form can experience "infinite bliss" & can then tell what is meant by that.
SINCE Shri Krishna is experiencing himself as Radharani, & he is Radharani, when they will interact, naturally Krishna too will experience Radharani who is "infinite bliss personified"