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I am currently playing on a new save I have mods enabled but nothing to mess with these two things, when I ask someone on a date we go to the location and I start doing the required tasks but it does not tick off then after about 30 seconds it ends and I get a bronze medal and if I need that date for an Aspiration 9 times out of 10 it won't count towards that.
I am playing a vampire teen if that helps in anyway?
Try dating someone else. This is a problem that I've only experienced with certain characters, such as the college professors from Discover University and the bar owner from Cottage Living. I don't play Teens very often, so I don't know which Teen characters might be affected, but I think most Teens should be okay. I don't think it's because you're playing a vampire.
You should also be aware that mods sometimes affect things they weren't intended to affect. Don't rule them out as the cause of a problem until you've tested them.
ETA: Sounds like playing a vampire teen might actually be the problem, after all.
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