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Just go on one date and then break up with him on that same date so his heart will be broken way more than if you said "no" right away. Joking, but it is a viable option. Still, as a Catholic, I'll say that guarding your soul is most important. A lot of people want relationships, but they care only for themselves. So, pray about I guess. What I said to start's still true though, if you want to break a heart.
ow, now i see... well, this is not my strong point but i will tell you that there is two way you can handle this. one is to take a change on this shit or two, give him the best fuck of his life and then break his heart... you choose
Don't do what jaggie says. If you screw him then you'll have to marry him to repent. Also, if he's already a whoremonger his heart won't break from a lay. If he has side girls, he must fall in love with you only, and then you break up. This aside, I pray you do what's right. Return good for evil (though not so sure what's evil bout this guy).
Or for ultimate heartbreak: become his fiance and then BREAK UP WITH HIM AT THE WEDDING DAY, AT THE PODIUM! Also, tell him you were just pranking bro. Now, that's true evil.