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Could mean two things.. When you regret not taking an opportunity to date someone you really love, and you regret not doing it.

Or.. Dating someone you wish you never did, you regret dating that person.

Love regret.
Example; I regret dating her now, she made me so unhappy.

Example; I regret not dating her now, she would of made me so happy..

Love regrets.
by Mr Psychotic July 01, 2010