I would like to know which of the following is the most natural construction to use when wishing someone good luck if both the direct and indirect objects are included.
1) Good luck to his finding a date.
2) Good luck to him finding a date.
3) Good luck to him on finding a date.
4) Good luck to him with finding a date.
According to comments they are all somewhat 'fine', but I personally find that number 1 sounds a little archaic and number 2 stilted to my ear. I was also told that usage of prepositions 'on' and 'with' in sectences 3 and 4 are uncommon in the context I provided. I find this strange because both, especially 'with', would be idiomatic if I take away the indirect object (the pronouns in my example).
i.e. Good luck with finding a date - perfect, no questions asked. Good luck to him with finding a date - sounds jarring and not very common usage.
Which one would a native speaker most likely spit out and if none of the four is satisfactory how can it be rephrased? Please address my doubts in detail.
Thanks in advance.