Should My Significant Other Be Contributing More Financially?

We're back on The Mail-In with Brett Merriman and Sally deFries in the chairs! Here's what we've got:

1. How do I ask my girlfriend to pay for more things in our lives?
2. Setting boundaries with in-laws who live within driving distance
3. I'm 6 weeks pregnant and have a history of miscarriage - how do I tell my parents I don't want to visit without spilling the beans too quickly?
4. How do I know if I'm settling?
5. Am I the asshole for not wanting to help setup/breakdown my buddy's wedding?

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