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So soon I'm getting a tattoo to say live without regret. I've pottered around on the internet a bit and found

Sine Paenitentia Vive / Vive sine Paenitentia for this. I assume this is correct.

I also want to pair it with the all too cliché Memento Mori, the previous line sitting above this. Would there be anything syntactically wrong with this? As two phrases? As a sentence with a break between them?

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You're very right to wonder about formatting the Latin language. The "truest" ancient formatting would be in all capital letters without spaces, i.e:

MEMENTOMORI

and

VIVESINEPAENITENTIA

It would be classically correct to separate these phrases by a line break. All that said however, I don't think it's necessary to stick with classical formattin. Spacing the letters will let the meanings be more recognizable to more people, which I think may be preferable to you?

In terms of lettering or fonts (I know you didn't ask about them specifically), there are some graffiti in Pompeii which could make an interesting font.

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  • That graffiti script is (old) Roman cursive, the usual script employed by the ancient Romans for handwriting on wax, papyrus and indeed walls. If I ever get me one of those Latin tattoos, it better be in Roman cursive ;-) – Sebastian Koppehel Oct 7 '20 at 22:36
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Sine Paenitentia Vive

seems to be okay.

Vive sine Paenitentia

on the other hand, should probably be "vive sine ulla paenitentia".

Hopefully someone more knowledgeable will point out if I am correct.

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    I think the "ulla" is specific, but I don't think it's necessary. On the one hand it would be "live without regret," and on the other it would be "live without any regret." – Nickimite Oct 7 '20 at 16:35

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