Jenn,

Congratulations on working so hard in getting your degree, waitressing, and making the switch and putting yourself through cosmetology school.  It must have been so rough considering how much your family went through with such losses.

I know honesty is so hard for people for reasons of shame and other things.  You might want to check out Bene’ Brown’s writings or TED talk around vulnerability and shame.

How to Move Let Go of the Fear of Judgment and Break the Silence of Shame

Part of being an adult is to have an adult conversation with your intimate, romantic partner about such hard things don’t you think?  You may want to start out the conversation is to tell him it is hard for you to have this talk.

Good luck,
Mark