Prerequisites: Complete A Chest Problem, give Reyner a Moon Brooch
Reward: None
Unlocks: Dating with Reyner
Given the events of A Chest Problem it seems pretty obvious that Reyner is open to dating you. Care to make it official? In order to trigger Reyner's romance quest you'll need to bring him a Moon Brooch. Moon Brooches can be acquired from Silky Stitch Tailor's, by interacting with the cash register at the front desk. Rather than buying Moon Brooches you'll need to exchange five Moon Cloves. You'll need to head back to the Clinic and heal more patients if you don't have enough.
Reyner takes the news with unrestrained enthusiasm, and manages to hurt himself again in the process. This is clearly something he'll have to work on - though he vows to try and take things a little easier from now on. The quest will end with Reyner giving you a somewhat-provocative sculpture. (And no, it doesn't appear to be a decoration you can place in your home.
Now that you've fully wooed Reyner you can choose to date him. Dating will take the pair of you to a location somewhere in Moonbury to enjoy some time together. That said, no time will actually pass while you're dating anyone. You can date Reyner once per day, so long as he's healthy and moving around Moonbury.