Does this mean in the dating sense?
Yes, but not exclusively. It can refer to any sort of 'seeing'.
My Israeli teenagers tell me that it's never used in everyday life to mean that you are dating someone. But grammatically it is correct.
What expression do Israeli teens use for dating? If I wanted to ask, are you dating her and the above is not used?
Are you dating her?=אתה יוצא איתה?
Oh god, that is so English.
why איתה? not אותה?
Because the verb "מתראה" requires "עם" (with) as a preposition.
How is this not the same as "Are you and she seeing each other?" in English. If it's reflexive, it's reflexive.
It is the same. I would report that.
non-native guess -- the verb is singular. Otherwise it's אתם מתראים זה עם זה, though I don't know if they actually say that. (more specifically אתה והיא)
אתה יוצא איתה according to my Israeli teenagers
Good to know, thanks!
Question to native speakers: is this really used in everyday life in israel, and what for?
What does this mean?
Are you seeing her?
I wasn't sure what the connotations were. as opposed to the denotations, which you provided me with.
It refers to dating, I think.
Ata mitra'e ita?
Does this verb have to do with seeing someone/something with your sight or does it have to do with meeting someone?
מתי אני רואה אותה אני מתראה איתה. :-) It drives me a bit crazy.
A calque from Russian: "ты с ней видишься?"
Or a calque from the Jiddish expression זען זיך מיט (meet and talk with), litterally "to see himself with".
Why "seeing" in the English answer. I think "meeting" would be better since this is not about using one's eyes but it ´s about two persons and if the arrange meeting with each others.
This is reflexive. It should be " Are you being seen with her?" Especially because איתה meant with her. This translation is slang at best.
I think it is reciprocal rather than reflexive.
Yes, in the same sense as when you use the infinitive of this verb, לְהִתְרָאוֹת, you mean, that you will be seeing each other again. It means "to meet personally", so that you can look at each other.
That doesn't sound correct to me. להתראות is "to see each other" not "to be seen with each other"