How to Handle Transaction(s)

Alice and Bob are married and have separate checking accounts; Bob is tracking both accounts in Quicken. In January, Alice buys $500 of lipstick using their joint charge card. Bob says that's a lot of lipstick so Alice immediately uses her account to write Bob a $500 check , but Bob is lazy and doesn't deposit the check till April.

Even though, in my mind, it is a 'transfer' between 2 accounts tracked by Quicken, selecting Transfer doesn't work well since the check written date carries over to the Transfer To account but that date is not the correct deposit date.

How should I correctly manage these lipstick transaction (there are more)?