The story goes, at least as I remember it, that when my parents sat down at the child-sized wooden chairs in our basement play room to tell me and my brother where babies came from, after a fit of nervous giggling (Dad's) my mom tried (unsuccessfully) to step in to finish the job.

It's funny on several levels, but mostly because my father was a professor of reproductive biology and had spoken often of such things in front of thousands of college students in lecture halls. And my mom, well, she'd gone through childbirth -- twice -- and still couldn't find the words.

If discussing the birds and bees can make a stoic man of science and a matter-of-fact mother falter, it's no wonder that when it comes to discussing sensitive topics in which we are far from experts -- namely, money -- we mumble, fidget, and retreat to the kitchen to do the dishes instead.

Brace yourself
Relatives, roommates, bosses, kids, neighbors, love interests, lunch buddies -- add money interactions to the mix, and things can get pretty awkward (the waiter forgets to split the tab; the cousin has a surefire investment opportunity; the in-laws expect you to join them on a lavish cruise, etc.). Or, worse, relationships and finances can be jeopardized.

It turns out that the key to handling delicate financial dealings is simple: acting! More precisely, you need to rehearse your lines before you're thrust into the spotlight by a difficult question.

So says Lizzy Post, the great-great-granddaughter of manners maven Emily Post.

"A lot of etiquette is about prevention. It is much more about making your life realistic and not being a pushover or a doormat for people," Post told me when I interviewed her about her book, How Do You Work This Life Thing?

Know what the situation calls for and be prepared for it, says Post, and "you almost never have to bite your lip and feel forced into doing something you're uncomfortable with -- financially or otherwise."

Things just got weird? Do tell!
Post's sage advice to calmly prepare for potentially awkward situations is appealing to both my "catastrophizer" disposition and my dream superpower of always having a quip or thoughtful response ready. For example:

Question: "Why aren't you married?"
Response: "Why are you married?"

Yeah, I know -- that one still needs some work.

However, when it comes to sensitive situations involving money, I've got your back. I'm compiling a list of prickly situations -- to address here on and on our Motley Fool Answers podcast -- and will present scripts, checklists, expert insights, and firsthand confessions to arm you with the right words and actions to handle whatever awkward money situation arises.

Here are a few situations you should be ready to encounter:

  1. Answering Your Kid's Pointed Questions
  2. Hey, Friend, Can I Borrow Some Money?
  3. Do You Have a Will?

Email me at with scenarios you've encountered, conversations you keep putting off, situations that leave you stumped, and humblebrags about deft ways you've dealt with awkward money situations.