Mi dovrebbe piacere andare con lei.

English Translation

I should like to go with you.

I don’t think the English implies an obligation.

Mi piacerebbe andare con lei. [?]

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Perhaps “I should like to go with you (but actually I don’t want to)”!

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In this case, “dovrebbe” does not necessarily imply an obligation. Think “ought”, in the sense “it should be desirable”.

It means roughly “knowing myself, going with her should definitely be a pleasure”.

Another example:

“Ti deve veramente piacere il gelato!” - which roughly means: “It really/definitely looks like you like icecream!”.

Also, without further context, I would translate lei as her, not you.

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My reasoning is based on the original English sentence being from the Tanaka corpus, and thus probably not written by a native English speaker. I think it follows the dated (?) grammar rule “you/he/she/it will (would); I/we shall (should)”, so in modern English it would be “I would like to go with you”, which would translate to my suggestion above.

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So… The sentence in question is here on Tatoeba:
https://tatoeba.org/en/sentences/search?from=ita&query=Mi+dovrebbe+piacere+andare+con+lei.&to=

The original Japanese sentence is

私はあなたと一緒に行きたいものです。

I am not completely sure about the 「ものです」 construct, but I think the sentence could be interpreted “I ought to like going together with you”. Actually, one explanation states that the meaning is “social norm dictates that…”

Maybe @MsFixer can help us here. Anyway, it looks like “moral duty” is implied, so “should” works, but it is probably weaker than the original.

Edit: ものです can be used also to state something is obvious/natural. So I think it cover both meanings of the Italian version. If that is true, it is fascinating how completely different constructs can cover the same range of expressions.

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Thank you @mike-lima for pinging me.
Tatoeba says the first pair is Japanese-English originally sourced from Tanaka Corpus (田中コーパス), a.k.a. “the biggest mistake the founder and her right-hand man made in the early stage of Tatoeba’s history”. And the Italian sentence is a derivative work from the English “should” sentence (ID: #252715).

The Japanese sentence means “I wish I could go with you”, and the connotation of ものです is “I wish, really. But the probability is quite low due to something uncontrollable such as my illness or busy work”. It doesn’t match the English sentence. So, you just need to ignore the Japanese sentence.

For more information about the accuracy of Tanaka Corpus, please read the article: “Using the Tanaka Corpus: Warning / Caution” written by an admin of Tatoeba named “CK”, an English teacher living in Japan.

Many English sentences sound old-fashioned and are not likely to be used today by any native speaker.

Most of the sentences were typed in by students as part of a project, but were not proofread by the teacher.

Unfortunately, Tatoeba imported 200K+ pairs from Tanaka Corpus. Some of them are removed, but there are still around 100K pairs on Tatoeba. Tanaka Corpus was translated in other languages. When you find unnatural and/or old-fashioned English sentences, please always check the yellow colored “tag” section on Tatoeba.

Like @morbrorper, CK also doesn’t like the English sentence and he posted his alternative English translation (ID: #1455318).

I’d like to go with you.

My conclusion is Tatoeba should delink between English #252715 (should) and Italian #2974964. And then, re-link between #1455318 (would) and Italian #2974964.

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@MsFixer, thanks very much for clarifying the issue!

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