I was reading the Japanese 攻略 (kouryaku, guide) wiki when I came across this information:
What. The. Fuck.
So apparently the reason why the date stuffs are not coming up is because I haven’t installed the Talk Pack DLC. All the Talk Packs (11 of them) which add to the ‘real life’ aspect of the game are apparently free (so the paid ones are Scenario + Costumes).
At first I thought about downloading the Talk Pack one by one (so that I can tackle each Date separately), but the wiki recommends to download all of them at once to avoid bugs.
But yeah, after installing them I managed to got a Shopping Centre Date card from Neriko while Ion was away. Supposedly I have to date in this spot for 7 times to get the 獅子狛夫婦 item… Let’s see how this whole thing turns out.