Wayne Leman at Better Bibles Blog has a good response to the common claim that Bibles should shoot for unreadability because Bibles have in the past helped foster literacy. (For a real example of this argument, see the comments on this post.) The key idea is that our translations should imitate how the original books of the Bible were written, rather than imitating how English translators have historically translated, as if the latter model is better than the scriptural one.
Bible Translation: June 2005 Archives
Then Jephthah fled from his brothers and lived in the land of Tob, and worthless fellows collected around Jephthah and went out with him. (Judges 11:3, ESV)
Some people think of the ESV as a more literal translation, though it's really just more willing to preserve the form of the original over the meaning of the original, and it's less willing to do that than some translations. Sometimes it's still too formal, as here. One thing that's just pretty stupid is to use an expression that's formally equivalent to the original term but that in the language you're translating into usually means something else. Translating something about close interaction among friends as "intercourse" nowadays is just stupid. You're altering the meaning by using a word that most of the time means sexual intercourse.
The same is true of the English expression 'going out with'. If someone had translated this verse this way seventy years ago, there would clearly have been no problem. Nowadays, if you say someone went out with someone else, we tend to hear it as a dating relationship unless contextual clues force us to do a double-take and lead us to try to hear it another way. In this case, that isn't immediate. These worthless fellows collected around Jephtah and went out with him. It first sounds funny to me, because it gives me the image of these guys trying to take Jephthah out for dinner and a movie, and finally I think about what it was supposed to convey nearly immediately afterward. An intelligent reader won't really assume he was having a romantic relationship with these worthless fellows, but the fact that it will strike some readers as an odd way to say it shows that it's a bad translation.
The NIV and NLT translate this as something like "they followed him", which is a little beyond the original meaning. The NKJV, one of the most formally equivalent English translations (though it uses a less reliable textual tradition as its basis in the NT) amazingly says "went out raiding with him", supplying a participial verb to clarify. The HCSB seems better than the NIV and NLT, saying they "traveled with him", but I think the sense of the NKJV is probably right, that it was more than just traveling. Believe it or not, the best of all the translations I looked at was The Message, which says "they went around with him". That gives enough of the sense of the original without overinterpreting it.