Preschool bestie's mom is my awkward nemesis

This morning Gabriel got moved up to the "big boy" class at school. They didn't warn us and he was sort of blindsided by it all, which of course made me feel extremely guilty as I was trying to peel him off of my leg to leave.

The good thing is that the majority of his friends were bumped up too, so at least there were plenty of familiar faces to keep him company.

One of those faces is a little boy in particular that Gabriel talks about all the time. This boy is the one friend Gabriel actually likes; when asked about any of the others he states simply, "They don't share." Literally every other kid. 

Gabriel is the worst sharerer ever in life so I'm not sure why he's obsessed with that. 

Anyway, I digress. Why is all of this significant? Remember when I had that awkward run-in with the pregnant lady at World Market? Guess who happens to be Gabriel's bestie's mom? 

So here's the sitch...Gabriel wants to play with this little boy outside of school and I'm at a bit of a crossroad.  I should probably get over myself and my awkwardness for the sake of my boy but I reeeaaallly don't want to. I get uncomfortable and say weird things as it is, so having to face this lady again is so unappealing, I'd probably rather eat dirt. 

But on the other hand, I know it would be so good for Gabriel to have a friend that he can have play dates with and enjoy outside of school.

I really need to get over my own anxieties and reach out, right? How would you go about approaching this whole thing?