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We're just having a discussion and we wanted to say:

"I was enjoying speaking with you last night"

Would we say this as:

Yo disfrutaba hablar con usted anoche

or

Yo disfrutaba hablando con usted a noche

Are either of these correct? If so, what is the difference between them? I was under the impression you could only use the gerund after using estar.

If it's valid, could I also say:

Yo disfruté hablar con usted anoche

and

Yo disfruté hablando con usted anoche

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The Spanish structure [disfrutar + verb-infinitive] should be translated as [enjoy + verb-ing] in English, and vice versa, in general.

There are some English verbs, like like, prefer, etc. that can take both to-verb or verb-ing. In general these are both translated using the Spanish infinitive. If there's any difference in meaning between the two English forms, it'll be lost.

I understand that your doubt stems from the fact that in English the -ing form (or gerund) can often be used as a verbal noun, while in other cases it functions as the present participle. The Spanish gerund (-ando, -iendo) doesn't do such double duty. Sometimes (as explained in another answer) you can have a gerund after some verbs like disfrutar, but it's not that usual, and the meaning is a bit different (in this case the gerund acts a complement of manner).

You cannot use a gerund after most of those Spanish verbs that can take an infinitive. In the following examples, the first sentence is OK and the second is wrong:

  • Me gustó hablar contigo.✓ | Me gustó *hablando contigo.
  • Prefiero comer solo.✓ | Prefiero *comiendo solo.
  • Elegimos no tener hijos.✓ | Elegimos no *teniendo hijos.

Unrelated to the actual details of your question, but having to do with it in a sense: yes, you can use the gerund (-ando, -iendo forms) with at least one verb other than estar using the same structure:

  • Ya vamos llegando. = "We're getting there already."
  • Se fue derrumbando de a pedacitos. = "It fell apart by bits and pieces."

Note again that [ir + gerund] has nothing to do with [ir + infinitive]! The former is used for an ongoing process, while the latter is a future construction.

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  • Excellent answer. You deserve the green mark, no doubt. Congratulations on your English, too. I've seen from your profile that you are from Argentina and, high as the level of English language teaching and learning is in our country, I haven't seen any local write so well in English in a long time.
    – Gustavson
    Feb 11 '17 at 0:17
  • I'm flattered (especially coming from you now that I've seen your profile). I'm actually learning about these things as I go.
    – pablodf76
    Feb 11 '17 at 0:54
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I'd definitely use "disfruté" in both cases. I'd never use "disfrutaba."

a) "Disfruté hablar" means that the talk itself was the source of your enjoyment. "hablar" is the object: "Lo disfruté" (I enjoyed it), so here "disfrutar" is a transitive verb.

b) "Disfruté hablando" (which is much less frequent) could be used to mean (a) or to mean that you enjoyed something else while you were talking to that person. The best translation would be: I had a good time/I enjoyed myself (while) talking to you (= as I talked to you) last night. Here "disfrutar" is intransitive and "hablando" is an adverbial of time or manner, depending on how that action is interpreted in connection with the enjoyment.

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  • In fact, the following sounds more natural for me: "Me encantó hablar con usted anoche."
    – Charlie
    Feb 10 '17 at 19:57
  • @CarlosAlejo You are right. That sounds better. "Disfruté" is a bit stilted. And then we have the much more informal "La pasé (adj/adv) hablando contigo anoche".
    – Gustavson
    Feb 10 '17 at 20:02

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