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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.

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    Frankly, all of those sound like an ironic or insincere wishing of luck. In addition, the fourth one sounds (much) less natural than any of the first three. – AmE speaker Apr 12 '17 at 2:26
  • Yeah, the sarcastic tone is actually meant to be there when I tried to say something like that. – JUNCINATOR Apr 12 '17 at 2:28
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    To me, all of them are fine except the fourth one. The third one sounds less sarcastic/insincere than the first two. – AmE speaker Apr 12 '17 at 2:30
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    To sound sincere, I guess you would have to say it with a smile, enthusiasm, no hint of insincerity, and maybe an exclamation point. Tone often makes the difference! – AmE speaker Apr 12 '17 at 2:37
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    Wait for a native speaker's answer don't rush to accept mine! – SovereignSun Apr 12 '17 at 12:47
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+50

None of the above

First, they're not all "somewhat fine". The first one is just wrong and this question is apparently the only time something like it has appeared on the internet. You aren't wishing luck to his action. You're wishing luck to him regarding his action. The third option wishes him good luck now that he has found a date (i.e., upon the event of his having found a date), which is presumably not what you meant.

The second and fourth mean the same thing and the shorter version is more common. There's nothing especially "uncommon" or "not fine" with the last option. "Good luck with that" is a fine phrase. "Good luck in ~" is even more common and left unmentioned. They're only awkward here because you keep adding additional clauses to something that should be a terse expression. If you wanted it to be so verbose, you wouldn't use the curt form "good luck" in the first place.

It's also just odd in general to be wishing "good luck" to someone in the third person at all. When it happens, it's mostly just describing someone wishing good luck directly. We bid him good luck... She wished him good luck... They said good luck to him...

If you really needed to tell someone you want to wish a third party good luck, the natural thing to do is to describe yourself doing it in front of them: I wish him good luck finding a date... I hope she has good luck with finding her own date instead of just stealing mine like she did last time... but when you do that it's much more common to leave out the topic. You say "I wish him good luck" after the context has already been established.

The still more natural thing, of course, is to wish "good luck" to the person directly and to describe the luck to other people. I hope he finds a date... I'd really like it if he found a date... It'd be awesome if he found a date...

  • Thanks for your detailed answer. I see that the kind of construction I am thinking of doesn't really occur much in real life conversations. But just to confirm, 'good luck to him finding a date', 'good luck to him in finding a date' and 'good luck to him with finding a date' mean the same thing and have nothing wrong with them grammatically. However, that would mean that the preposition is only optional correct? Would you include it? If you have to use one of the these three constructions, which one would you use? – JUNCINATOR Apr 26 '17 at 11:18
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    @JUNCINATOR Myself, I'd say "good luck on him with finding a date" but that's because I'm saying something odd anyway, so why not be archaic about it? If I were trying to be a smart ass, I'd just use the terse form without a preposition. – lly Apr 26 '17 at 13:50
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I'm a non-native speaker and that's what I know.

We use different prepositions with Good luck such as to,with,for,in,at and on. Some are interchangeable, some are rare and uncommon, some don't sound right in some contexts.

In your examples:

  1. Good luck to his finding a date. (Incorrect)

  2. Good luck to him (in) finding a date. (Correct)

    • A gerund can take either the genitive (his) or the accusative (him) as subject. (Source).
  3. Good luck to him on finding a date. (Correct)

    • We can use "Good luck on" to refer to an action, an event and time/date. It can also be followed by a noun, gerund or a possessive adjective.

    Examples:

    • Good luck to him on Friday.
    • Good luck to him on his party.
    • Good luck to him on buying a new house.


  4. Good luck to him with finding a date. (Correct)

    • Few examples on the web tell us that this exists but is very uncommon among people. However, this doesn't sound grammatically wrong. The most popular example using "Good luck to [someone] with" is: "Good luck to him/her/you with that!".

Apart from these options you could also say, "Good luck to him in finding a date."

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