Source: American TV dramaMary: Um, not so good. He walked me to the subway and said,"We should do this again".
Lisa: What? He said,"We should do it again, that's good, right?"
Lily: Uh, no. Loosely translated we should do this again means you'll never see me naked.
Lisa: Since when?
Peter: Since always. It's like dating language.You know, like "It's not you" means "It is you".
Or you are such a nice guy mean "I'm gonna be dating a leather-wearing alcoholics".
(I just gave each person a name, which is not exactly the name in the drama because I don't remember their names)
Mary went to meet her friends, and they asked about how her date was.
Do you think "we should do that again" really mean "we shouldn't date again"?
It depends on whether the person means it or not. The other people don't seem to think that he does.
There is something a little unenthusiastic sometimes about "We should do this again" or "Let's do this again sometime". It can just be a polite way of the person saying "I probably don't want to see you again but I'm trying to be nice so I'll pretend I want to see you again but we won't actually make a plan".
If someone said "Wow! That was the best evening I've had in ages. It was really fabulous and I can't wait to do something like that again with you. Get your diary out and let's see when we're both free!" then I would think they wanted to see me again. (I would probably also think they were a bit over the top and perhaps a little too enthusiastic!)
Remember - if you don't use correct capitalisation, punctuation and spacing, anything you write will be incorrect.
Yes, I have had many first dates. They are mostly an informational question and answer period. Sometimes things really click on the first date, but often the click doesn't come until the second or third date, and sometimes never. For me, "we should do this again" is neutral, but it implies an interest in continuing to find out if something is there.