Like a Dragon: Infinite Wealth - 4 - Substory 7: Miss Match
One of the first substories you can access after you have freedom in Chapter 3! This one starts at the little park between Waikiki Street and Seaside Avenue where a lady will approach Ichiban as she mistakes him for her date.
This leads to meeting Machiko-san, creator of the popular Miss Match dating app who will introduce the associated minigame to you!
If you've played Yakuza 6 and did live chat in it, it's somewhat similar but goes more in-depth as you can tailor your profile to your liking and need to pick the best possible answers before hitting the button combinations to send them properly.
You'll usually have to pay, but the first time's free, so take the chance to learn the ropes, laugh at Ichiban's silly and sometimes cringeworthy replies, and do your best with no pressure!
This substory may have a very silly premise and execution, but it does lead Ichiban to a realization by the end, so who knows? It may be worth it to check out the app again in the future, when we have money to spare!