Friends
Dear Toolsie,
idk if i shld tell my bff her bf is cheating??? like we're not even that close anymore but i saw him w someone else and idk what to do
Toolsie wrote back.
New to Dear Toolsie?
These three show the range on purpose — a friend's loyalty tangled up in gossip, a marriage's money resentment that's more about being seen than the dollars, and the quiet doubt of starting over past fifty. Different situations, same thing underneath: someone who already half-knows the answer and needs it said out loud.
The kind of loyalty tangle that has no clean answer — worth reading for how bluntly Toolsie cuts through the 'not my business' hedge.
Small dollar amounts, real resentment — a good example of Toolsie naming the actual issue instead of refereeing the math.
Money
Dear Toolsie,
Dear Toolsie, my husband and I have separate accounts but he 'forgets' to pay me back for shared bills constantly. It's not huge amounts each time but it adds up and I'm the one who always has to bring it up.
Toolsie wrote back.
Proof this isn't just conflict-resolution — it answers the quieter, bigger questions too.
Identity & Values
Dear Toolsie,
Am I too old to start over in a completely different career at 52?
Toolsie wrote back.
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