I've had 4 sims diving around the clock for days for these to medals. I can never get them! I miss every hobby and quest of the free packages even doing around the clock with ALL sims I have. NOT RIGHT. I can't afford to buy LP to get the cool stuff or to level up or speed up!!
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Try having them do the shortest timed dive they can and see if they can't unlock anything after a while. You can also try doing the longest timed dive. If neither work than you may need to get to the next level in the Diving Hobby. I'm having this problem with the Fishing and Fashion hobbies as well so you aren't alone.
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