Hiya Jennifer - welcome to
planDisney!
We're so glad you stopped by with your question - I'm here to help!
Food is probably my favorite part of a
Walt Disney World Resort vacation! I love all the delicious food options and experiences available in the Theme Parks, Disney Resorts Collection hotels, Disney Springs, and beyond.
Advance dining reservations can be made starting 60 days prior to arrival, so you're not too far behind! There should still be plenty of availability, but you might need to be flexible on location or time. As you've already alluded to in your question, splitting up your group is a great way to open up more availability.
If I'm understanding your question correctly, I think that
you are the overlapping Guest if you are the person making both reservations. The system will not let you hold multiple overlapping dining reservations made by you. The easiest way around this is to have someone else in your group who already has a My Disney Experience account, and is not listed on another reservation during the same time window, make the second reservation. When making reservations, you don't actually have to assign specific people from your Family & Friends list - you can just leave them as Guest 2, Guest 3, and so on. The only downside to this is that the reservation will only show up in your plans, and not in others' plans, but it also won't prevent them from making another dining reservation at the same time.
If you're not finding the exact reservations you were hoping for, be sure to check back closer to your trip. Other Guests' plans change all the time, and when they cancel a reservation, it then becomes available for others like you! I've noticed that most cancelations tend to happen between 24 to 72 hours in advance - make sure to check and you might be surprised by what you can snag! During my last trip, just before bed, we were able to get a reservation for the amazing Character Dining breakfast at
Topolino's Terrace - Flavors of the Riviera for the next day!
I hope this information helps you continue planning for your crew -
please let me know if I can help answer any other questions for you!
Ryan J.