Is anyone else having issue with dates (in game not in real life, though my track record there is pretty abysmal, but I digress)? I've had my couple (Jake and Hunter) who have maxed out both relation...
Ironically the most difficult thing to accomplish on a date is "socialize 10 times". Friendly and funny interactions usually do it, but takes time. Romantic interactions don't count as 'socializing', which is a bit silly, but whatever.
Talk about things, ask things, complain, compliment, use any extra ones like enthuse.
The rest is usually easy like flirt 3 times, flirt while flirty, sit and talk, give a massage, deep conversation 2 times, etc...
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