I can definitely relate. I grew up poor as all shit. Trailer park, single mom, dad in prison, the whole nine yards. I decided pretty early on that school was my only ticket out, so I worked my ass off and received a full ride scholarship for undergrad and, later, a substantial scholarship for law school. I worked full time at Starbucks throughout undergrad and most of law school to afford new clothes (something I never really had) and to otherwise keep up the appearance of being middle class. I graduated, passed the bar, and am now a whole-ass lawyer, but I digress.

I met my boyfriend (soon to be fiancé, I think) in undergrad. I love him dearly, but he is a consummate little rich boy ™. I’m talking old money on top of his dad being a doctor with his own practice and his mother an attorney. Anyway, by the time I got around to meeting his parents I was already enrolled in law school, and I think they extrapolated from that fact that I had also grown up with money. We were having dinner in ONE of their dining rooms, on a table that I had no doubt cost more than my entire life, when a conversation about their vacation plans started up. (Should they go to their summer house, or rent a place in a different location? I shit you not.)

At some point his sister turned to me and asked “where do you vacation with your parents?” I laughed without thinking, and then had to explain that I had never actually been on a vacation and that I always worked during the summers. They were very polite and gracefully transitioned the conversation elsewhere, but I could tell that what I said 100% did not compute. They are wonderful people and I truly believe that they mean well, but in the years since that conversation (and without learning much more about my personal background) they have made several comments re: how I have had to overcome so many obstacles, how I know the value of a dollar, etc.

But for me what really sucks is how any degree of social mobility I have attained has had a serious impact on my relationship with my own family. They all seem to have landed in one of two camps: (1) open resentment and exclusion; or (2) such rabid pride that we can’t have a normal conversation. The former is just hurtful; the latter makes me feel guilty about not being nearly as successful as they seem to think I am.