Richie brought Risa out to eat. He actually wanted to talk to Risa about her friends. Maybe he likes to spend some time with them and get to know them? I find it a bit odd, as Rich is a tad bit older than all of them. I guess he just wants to know if Risa’s friends are good kids.
In this comic, Rich was distracted by the intent of ordering desserts. It’s a bit odd to order desserts before meals in a restaurant, but that seems to be something that Richie does all the time. I guess Risa isn’t the only sweet-tooth in the family.