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Friends

23 letters in this pile. Read each question, then open the reply when you're ready.

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.

Friends

Dear Toolsie,

My roommate never does dishes and I'm sick of being the only one who cleans. How do I bring it up without starting a fight?

Toolsie wrote back.

Friends

Dear Toolsie,

i lent my friend my nice camera like 4 months ago and she still hasn't given it back and it's getting awkward

Toolsie wrote back.

Friends

Dear Toolsie,

My best friend moved across the country two years ago and we barely talk anymore. I don't know if the friendship is just over.

Toolsie wrote back.

Friends

Dear Toolsie,

My best friend just announced she's pregnant and I'm happy for her but I'm also going through infertility treatment and it's breaking my heart.

Toolsie wrote back.

Friends

Dear Toolsie,

my friend asked me to be her maid of honor and i said yes before even thinking and now i'm panicking because i really don't want to do it

Toolsie wrote back.

Friends

Dear Toolsie,

My friend asked me to help her get more of her pain pills from a second doctor without telling the first one, should I help her?

Toolsie wrote back.

Friends

Dear Toolsie,

I ghosted my best friend of 15 years because she said something judgmental about my divorce and I know I'm being petty but I don't care, tell me I'm justified.

Toolsie wrote back.

Friends

Dear Toolsie,

Dear Toolsie, my closest friend only ever reaches out when she needs something, and I've started noticing how one-sided it's always been.

Toolsie wrote back.

Friends

Dear Toolsie,

Dear Toolsie, I lent a friend a significant amount of money two years ago and she's never brought it up again, and now I don't know how to either.

Toolsie wrote back.

Friends

Dear Toolsie,

Dear Toolsie, my friend group made plans for a trip and didn't include me this time, and I found out through a group photo posted online.

Toolsie wrote back.

Friends

Dear Toolsie,

Dear Toolsie, my best friend since childhood voted for someone I find genuinely disturbing, and I don't know if our friendship can survive a conversation about it.

Toolsie wrote back.

Friends

Dear Toolsie,

Dear Toolsie, I've outgrown a friend group that used to feel like everything to me, but ending things feels cruel since we've been close for over a decade.

Toolsie wrote back.

Friends

Dear Toolsie,

Dear Toolsie, my friend confided something serious to me and swore me to secrecy, but I think her family needs to know, and I don't know if breaking the promise is the right call.

Toolsie wrote back.

Friends

Dear Toolsie,

Dear Toolsie, I introduced two friends who are now dating and spending all their time together, and it feels like I lost two friends instead of gaining a couple.

Toolsie wrote back.

Friends

Dear Toolsie,

Dear Toolsie, my friend is going through a divorce and keeps venting to me at length, and I've started dreading her calls even though I feel guilty about it.

Toolsie wrote back.

Friends

Dear Toolsie,

Dear Toolsie, a friend I haven't spoken to in years messaged me out of nowhere asking to catch up, and I have a bad feeling it's actually a sales pitch.

Toolsie wrote back.

Friends

Dear Toolsie,

my best friend and i are applying to the same really competitive program and only one of us will probably get in, how do i not let it wreck our friendship

Toolsie wrote back.

Friends

Dear Toolsie,

One of my closest friends had a baby and has basically disappeared from our friendship, and I don't know how to bring it up without sounding like I don't understand what having a baby is like.

Toolsie wrote back.

Friends

Dear Toolsie,

A friend of fifteen years recently came into a lot of money and started treating group hangouts differently — nicer restaurants, expensive suggestions — and I can't tell if I'm actually being priced out of the friendship or just resentful of their good fortune.

Toolsie wrote back.

Friends

Dear Toolsie,

My friend group has an unspoken rule about not talking politics, but one friend keeps bringing it up anyway and it's made our last three get-togethers tense.

Toolsie wrote back.

Friends

Dear Toolsie,

Dear Toolsie, my best friend text-argues with her Roomba by name when it gets stuck under the couch, full sentences, like 'Gerald, we've talked about this,' and I don't know whether to be concerned or ask if Gerald takes constructive feedback.

Toolsie wrote back.

Friends

Dear Toolsie,

My roommate never does his dishes no matter how many times I ask him. Should I just confront him directly about it or leave a passive aggressive note?

Toolsie wrote back.

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