15 Teves 5764
Is it permissible to go on a date with a guy whom you will probably break up with… especially if he is going to pay?
Thank you for your interesting question. If you are only going out with him to lead him on and have a good time at his expense, this would of course be forbidden because of Geneivas Daas. However, if there is even a slight possibility that you would be interested in marrying him if he would manage to impress you on the date, it is permissible, and of course a Mitzvah to see him. Also, if you know that he is not for you, but you agreed to see him again so as not to hurt his feelings by dropping him after one date, it is also permitted and a Mitzvah to see him again. It makes no difference in either of the above cases whether or not he is going to pay.
Rabbi Aaron Tendler