Becoming friends with women who entertain misogyny, whether ambivalence around motherhood is a sign it's not for you & when a friend of 20 years asks you to borrow money - should you lend it to them?

This week, in the Dear Clementine inbox: 

• I have made some very lovely new girlfriends however, they are friends with a group of men who are absolute misogynists. Should I speak to my friends about this or just get rid of them all together? 
• I’m in a serious relationship with a partner I love. However, we are at something of an impasse when it comes to deciding whether to have kids or not. I just don’t know, all I know is that I’m ambivalent. It seems that so many people around me simply can’t accept that a child-free life can be fulfilling. Is there any right way to work through this ambivalence? Do you have any advice?
• I have a best friend of about 20 years. Today for the first time in our friendship she asked me to lend her $350. One of my boundaries is that I don’t lend friends money. When I told my friend she got very upset with me. I feel like the simple act of me saying no has damaged the friendship. What can I do to feel better and hopefully turn this into a learning experience?

If you have a question for Clementine, send an email to [email protected]

See omnystudio.com/listener for privacy information.