It seems like you are dedicated to getting her to acknowledge her privilege, like it's an obstacle you have standing before you. If you know this is who she is, why do you continue to let it bother you? Everyone, each of us, operates from our own experiences. I have friends from any number of different backgrounds. They each bring their past, culture, emotional history, etc. with them (as do I) whenever we interact.

How is this different from anyone else?

Anonymous wrote:I have had a friend for many years, and would like some advice on how and whether to continue our friendship.  We became friends through a mutual friend when we both lived in another city.  My friend is from an extremely privileged background.  While she has worked, it has never been a standard employer-employee relationship where there are expectations about performance, hours and set vacation time.  She had her own company that her family financed and worked directly for her family.  I, on the other hand, took out loans for school and have worked full time since I was 16 years old, dealing with difficult bosses and having to manage finances.  We both have families now, and my friend is a good person.  While we don't live in the same city now, she calls regularly, comes to visit, invites us to visit her, etc.  My struggle is that our conversations involve her endlessly telling me about her life, full of parties, vacations, nannies, playdates, and now working from home.  She does not acknowledge that her circumstances are unusual, but rather has a tone of “this is how” to do things.  When I call her on it (for example, noting that a nanny is too pricey for some or that working from home is not always an option), there is either an awkward conversation or silence.  Updates about my full-time working life with kids and a hectic schedule are brief and awkward.  I have a handful of friends that I’ve known for many years, and we are all very different, so I’d like some advice on this particular friend.

Anonymous wrote:Don't feel bad about cutting ties. Sometimes you have to re-evaluate friendships. Free time is precious and limited - don't spend it on someone you don't like.

Anonymous wrote:

+1

It works both ways. Sometimes people expect handouts, or to be "treated" for everything, or cry poor mouth, because they try to count others' pennies. OP, if the money will always be an issue, you need to have other friends with whom you relate better. But crying poor mouth, then posting about your extravagant meal out, with expensive wine, that costs hundreds of dollars, is not a good idea. People can be out of touch on both sides, you see.

Anonymous wrote:I once had a rich friend that got a multi million dollar settlement from a botched surgical procedure lawsuit. This woman did not come from money but money changed her into someone I slowly over time started to dislike.

She flaunted the money and made everyone around her feel it's too bad you're not as rich as I am, we could have so much fun. You know the type.

Let it go and find someone you have more in common with.

Anonymous wrote:I have had a friend for many years, and would like some advice on how and whether to continue our friendship.  We became friends through a mutual friend when we both lived in another city.  My friend is from an extremely privileged background.  While she has worked, it has never been a standard employer-employee relationship where there are expectations about performance, hours and set vacation time.  She had her own company that her family financed and worked directly for her family.  I, on the other hand, took out loans for school and have worked full time since I was 16 years old, dealing with difficult bosses and having to manage finances.  We both have families now, and my friend is a good person.  While we don't live in the same city now, she calls regularly, comes to visit, invites us to visit her, etc.  My struggle is that our conversations involve her endlessly telling me about her life, full of parties, vacations, nannies, playdates, and now working from home.  She does not acknowledge that her circumstances are unusual, but rather has a tone of “this is how” to do things.  When I call her on it (for example, noting that a nanny is too pricey for some or that working from home is not always an option), there is either an awkward conversation or silence.  Updates about my full-time working life with kids and a hectic schedule are brief and awkward.  I have a handful of friends that I’ve known for many years, and we are all very different, so I’d like some advice on this particular friend.