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¿Question #839?
EndersGame: What is the hardest phone call you've ever had to make?

ocdspectrum: Definitely a rotary phone.
Fribian: Hey sister! I've hit rock bottom. I'm coming home. Ya got room on the floor somewhere and a place to stack my stuff?
historyguy71: They're all pretty easy, I just push the buttons. Unless it was a rotary phone, those are harder.
MisterCranky: I will answer this later, when I think of something hilarious to say.
hob69: Gosh. I'd really have to think about that, and I don't think I'd much enjoy doing so.
MamaRat: Phone interview. Interviews scare the living crap out of me.
Woelf: Pretty much any call that requires leaving a message on an answering machine or voice mail. I hate those things, and have to willfully restrain myself from hanging up the instant I hear one kick in.
Cygnus2112: just after I took the viagra...
beerbear: Prolly the time I got that bottle stuck.
gmonk: Calling the taxi when I was too drunk to drive. I had to do it, but I'll be damned if I could remember the number. Hailed one outside the phonebooth instead.
engdy: I once had to fashion a phone booth out of empty coconut shells when I was stranded on an island. Man, that sucked.
kathleenryan: I say the most difficult things in person, never over the phone.
tankexmortis: An international call, probably. Gotta dial all kindsa crazy-ass numbers. It's hard.
mbrna: The one to tell my wife to say goodbye to our dog.
DancesWithBeagles: The series of calls I had to make to relatives to let them know my father had died.
MotUfan: I don't recall off the top of my head.
DHEK: Hmmm... a phone call to a prospective employer to conduct a phone interview.
TheArchAngel: Calling my brother to tell him that our Mother had died...he was in the military at the time
aleo09: none really
Butterbane: The endless one at work.
Ebon Wendigo: I had this phone card which required me to enter quite a long string of digits and it took me several tries to get it right.
airborne101: to china the operator would never shut up
King In Yellow: I broke up with long time girlfriend over the phone....that was the hardest call I ever had to make...pretty lame
joebelanger: That's personal.
ezradenney: Telling my Vet it was time to put my cat to sleep.
Dorque: Calling Dad after 8 years of not talking.
hellsbishop: I've recieved some crappy ones, but make? Not really sure, none really spring to mind.
Helenoftroy: Dad, I'm not coming home.
dietevil: I usually do the hard stuff in person rather than on the phone.
Dave: I once worked for Prudential for seven days, and I had to make endless cold calls using the phone book.
brainrob: That's just too personal
aramis: "operator, can you tell me which state I'm in?"
locusshifter: I Plead the Fizitfh
Loquutus: no comment
EDS Teioh: all of them....social anxiety
GrandpaDave: To my dad, to tell him he wasn't invited to my graduation party because my stepdad doesn't like him.
matthew.marquand: Called the vet to schedule a euthanization of my cat (renal failure)
The Unbeliever: 42
CharlieWonka: Had a few but none specific I can think of as the hardest.
Karlsen: The one to the person who's phone number I didn't have
Randy Cox: Damn. Here's another one of those questions where you have to pause and actually think. What do you think GeekQuestions is for? Anyway, I had to call someone and tell them their uncle had committed suicide, but I'm not sure that was harder than calling a co-worker to try to arrange a date. And there's probably something worse in there, I guess.
davedanger: ?!?!?!
scriptorum: All the hard phone calls sort of blend together in memory.
kimapesan: The 877 number... *slap* bad thought, go away...
ThatFalafelGirl: umm...probably calling to order something from a company, i get all freaky-panicked.
BaSL: the one with the most numbers
Mike A: I was trying to call my wife at work. I can't remember why, but it was important. The phone broke so whenever I pressed "0" it dialed "8" or something like that. I kept getting an increasingly irate lady on the phone who wouldn't tell me her phone number so I could figure out which digit had issues. Bah, what a pain.
skrutsch: When my Mom died, I spent the day on the phone calling friends and relatives from her address book.
mandj2001: calling a client to decline them for insurance because their blood test showed the presence of herpes
Lord_Prussian: dunno
snoozefest: na
melissa: Probably the calls when my mother-in-law died.
Metaphora: I had to call and retract my acceptance of a job offer. My boss counter-offered when I gave notice, and the offer was far too good to turn down.
gnomehome: The one that was none of your business.
Spaten: the one where i called in the air strike
pkreynolds: From Europe to America. Subject will not be disclosed.
2amp: reporting a death
Malacoda: Report the death of my father.
puffinge: Your sister Rose is dead.
AlorielLelyn: To the vet, making an emergency appointment because my cat was having seizures - knowing full well she was dying, and suffering horribly. Meaning I would have to consider euthanasia...
kennyb: too dang personal
sos1: Oh man, it was in London, 1969, I was young, and I couldn't figure out those payphones to save my life. Fortunately, the call wasn't that important, because I gave up after losing huge amounts of shillings and never getting through.
Blackwind: The one to your parole officer
Bluenose: When i rang my mom and asked her what she was wearing.
CortexBomb: Well, this one time I had to dial using only my nose...and it was a rotary
djlg: Keeping my girlfriend's grandmother talking while her family drove over to tell her son had been murdered.
haraggan: Most of them. I hate the phone.
raolsson: EG, what is it with you and the painful questions? Probably my first because I wasn't sure how to use the phone.
BobDodgerBlue: To my Mother to tell her my Son had medical problems (they turned out ok)
Michael Becker: calling my parents back when my grandmother was dying from Cancer
fsumarc: to tell my mother that my little brother died in a car accident. I now dislike you.
chaddyboy_2000: I've never had a tough call to make.
Ludocrazy: Call my aunt to tell her my mother died.
nienie: to my dad's girlfriend
Claytonius Maximus: Hello, Ed McMahon, I'm calling to arrange pickup of my MONEY.
jttm: I don't know. Nothing really.
Shakar: Informing someone of the death of his friend.
ValJor: Better not talk about these things
CDRodeffer: When my grandpa died.
ynnen: The one to tell my mom she wasn't allowed to visit her first and only grandchild after he was born -- she had the flu but was insisting that she was OK and wouldn't cause a fuss.
tragicpoet: I was arrested for shoplifting when I was like 8, I knew only my mom was home
skelebone: I usually send telegrams when I don't want to talk on the phone.
queequeg: Calling my mother to tell her I was getting engaged