"Als" in the sense of time at the same time as "als" in the sense of "than"

Question

Sometimes I have an inclination to compare something to some other time in the past when I took a particular course of action.

For example, if I was talking about referring to a time in the past that I asked a question, I might use a relative clause "Als ich dich zuletzt gefragt habe"

But if I also simultaneously want to express a comparison to that relative clause using "als", I don't see a way of doing that grammatically.

Example sentence: "You were angrier than the last time I asked"

My brain spits out "als als", which seems ungrammatical and I falter until I can reword it.

The only thing I can think of that sounds reasonable would be something like "als damals, als"

Is there a preferred way of handling this situation fluently?

Answer 1

You were angrier than the last time I asked.

Du warst wütender als das letzte Mal, als ich gefragt habe.

The comparison goes first, then the adverbial clause that further explains the comparison.

Answer 2

First, in colloquial language, feel free to say als als. It may not be beautiful, but it isn't wrong, and often won't even be noticed.

Second, to avoid the ugly repetition, German speakers often employ the trick that in the sense of “than,” als has the synonym denn. So you can for example say:

Herr Sowieso gefällt mir besser als Kunde denn als Kollege.
I like Mr So-and-so better as a customer than as a colleague.

This is a somewhat educated level of speech, but not too much, in my opinion. In written correspondence (e.g. business emails), I would definitely use this construction, or else rephrase the sentence, to avoid als als.

Outside of this usage, denn in this sense normally only occurs in extremely dated language or fixed expressions like Geben ist seliger denn Nehmen. ¹⁾ In a number of other senses, it obviously remains a very common word.

I do, however, agree with Janka that when you translate the English example you gave, you should not encounter the als als situation.

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¹⁾ Acts 20:35 “It is more blessed to give than to receive.” Unfortunately, nowadays even this is often cited as: … als nehmen, thanks to the Protestant busybodies who, despite all evidence to the contrary, believe they speak better German than Martin Luther.

Answer 3

Both, "als" and "wie" have their place in comparisons. As a rule of thumb, one uses "als" when using the Komparativ, "wie" when not:

Er ist so groß wie ich.
Er ist nicht so groß wie ich.

but:

Er ist größer als ich.
Er ist größer als ich.

Notice, though, that the usual reasoning with which this is presented, is wrong: in school we learned (I paraphrase here):

"Als" wird nur nach Komparativen und dem Wort "anders" davon abgeleiteten Wörtern verwendet.

Correct is: in these cases one cannot use "wie". "Wie" expresses a comparison, "als" a measurement! This means:

Eine Sache bedeutet soviel wie eine andere.

One thing means as much as another thing, both mean the same (measured against an implied third). I weigh as much as my neighbor - if we both are to be weighed we'd both get the result "X kg", the "kilogramm" as the unit of weight is the implied third.

Eine Sache bedeutet soviel als eine andere.

One thing means as much as the other thing is, it means the other.

Das rote Auto wiegt so viel wie das gelbe.

Comparison.

Das rote Auto wiegt zweimal so viel als das gelbe.

Measurement.

Here is an article (in German and my English is not good enough to faithfully translate the nuances of the authors masterful language) where this is discussed in detail.