Welcome aboard, Linda!
My family and I love dining during the second seating onboard our Disney Cruise Line vacations.
Since your boyfriend is used to eating late, I'd definitely recommend the second seating for your meals. He'll be happier, and you'll get more time to relax and rest up after a long, fun day onboard or in the ports of call. My family and I enjoy that we don't have to rush back from our Port Adventures to quickly shower and get ready in time for the earlier dinner. Instead, we take our time, (sometimes a nap), and enjoy a relaxing start to the evening by showering, getting ready and then heading off to the first of the performances of the Broadway-style show. Sometimes when we really need an extra rest, we don't shower and get changed for the night until after the show, before dinner. Either way, it's a calmer start to a fun night, and we really enjoy that, so I think that's probably the best bet for you two as well.
Disney Cruise Line features
Rotational Dining, so you'll be assigned a rotation that will take you through the three main restaurants onboard. Your same dining service team rotates with you, so they get to know you and your preferences, and you get to know them! Meals are included in your cruise cost, so no extra cost associated with the restaurants. The only exception is if you book a meal at Palo or Remy, the two Adult Exclusive restaurants onboard, which do carry an additional cost. I highly recommend dining at one of them.
Palo is always a favorite for my husband and me. You can book these when your window for online check-in opens prior to sailing.
Have such fun planning, Linda, and please stop back again if you have further questions! We'd be happy to "sea" you again!
Marcy