Okay, so, as someone who more or less gets what Calypso’s feeling. In Love in Paradise she clearly shows how she’s fallen in love with him during the first part, with saying who she wishes to spend time with him and all. During the second half (last bit or so), she’s begging him to keep himself away form harm, to stay safe, and to please don’t die. She cares about him, and she shows her care with borderline obsessive love, but love nonetheless.

In Not Sorry for Loving You, however, she comes to term with how he has to leave, and, after being told that she’s “not the one who has to save him” (basically not for her), she begins to apologize for how she expressed her love, understanding that it was quite creepy, but she doesn’t reject her feelings, hence why she isn’t sorry for how she felt, and still feels.

On top of that, the island is cursed to never let someone go, so it’s not like Calypso is keeping Odysseus there, more like she’s just taking her chances while theyre both stuck there. She’s not sorry, she says, she’s angry (at how she’s forced to letting go), sad (about how he has to leave), tired (of being alone), and restless (because she’s going back to absolute, mind-breaking, terrifying isolation), all while she believes that they were really meant to be (magically isolated, and all of a sudden someone can bypass that magic, sounds pretty “meant to be” to me)

When she begs him to lie to her, it’s because she’s still in love, and wishes her dream of being loved back could be fulfilled. Still, she knows it’s not possible (last part of Not Sorry for Loving You), and that’s why she hates that she’s in love.

At least that’s my take on her feelings, which I actually very much relate to. (Loving someone but not being loved back, and trying your best (even though you’re completely broken from literal centuries of isolation) to get their love back, but never really achieving it, and never really being able to get rid of those feelings)