First off, please accept my sympathy for your wife’s passing. I hope that you can remember the reasons that you loved her to help you through this time.
In addition to what Flint said, let me give you two reasons to allay your concerns. (1) I’ve talked with many of the ladies at Sheri’s, and they’ve all been compassionate people. I’m sure they understand that some times things don’t go as the man planned (and this happens to all men, not just older ones). If something like this happens, the lady you’re with can handle it with empathy.
Also, when the ladies get a gentleman for GFE, I am virtually certain that they would look forward to that gentleman returning at another time. So establishing rapport is just how things proceed naturally.
Hope everything goes well!