Chatting with Prince on AOL in 1999

Screenshot of an email to me from Erica

Before the Internet as we know it today, before social media, there was AOL. Specifically there was AOL chat rooms. The digital world was smaller then but Prince was always there. He was so ahead of his time digitally. The Purple One did group chats with fans all the time on AOL. A “room” in AOL chat parlance was like a Twitter DM — a private chat room.

Six years ago my friend Erica Kennedy and I were talking about what she was going to write for her next book. She had just released her second book, Feminista, and was pretty well known for her first book, Bling that satirized the music industry that she came up in. We had the idea of a Kindle Single detailing her interactions with Prince while she was working on a profile for InStyle Magazine. You can see photos of Prince’s Spanish Villa and a few lines of Erica’s AOL chats with Prince over at InStyle now.

This is the AOL chat log detailing her interactions with Prince that Erica emailed me while we were planning her novella.

Here, of course, “NPG — -” was Prince’s private AOL chat handle at that time while Ekj4 is Erica. I have kept all the typos exactly as they occurred in 1999.

Erica K to me - u r the 1st person 2 c this outside of the N style staff.

NPG — -: high
Ekj4: hi 2 u
NPG — -: is ur last name kennedy?
Ekj4: no it’s my middle name that i use for writing, trying to stay on the dl
NPG — -: r u alone?
Ekj4: sure am
NPG — -: have u ever spoke in private chat space?
Ekj4: all the time!
Ekj4: i’m a terrible typist though
NPG — -: would u like 2 go a room?
Ekj4: what room? what’s wrong with this way?
NPG — -: don’t like
Ekj4: ok, where’s the room?
NPG — -: it’s called…
NPG — -: amatteroftime
Ekj4: how do i get THERE?
NPG — -: use the icon that says….people
NPG — -: c it?
Ekj4: yes. and…
NPG — -: start ur own chat
NPG — -: private
NPG — -: type in the space….amatteroftime
Ekj4: is it only going to be u and i?
NPG — -: yes
Ekj4: ok
NPG — -: scared?
Ekj4: no
NPG — -: yea,right!
NPG — -: r u there?
Ekj4: yep

NPG — -: is ur hair done?
EKJ4: it’s up in a ponytail and truth be told, it’s lookin’ kinda busted.
NPG — -: lol!
EKJ: my hair doesn’t have the bounce of your ‘do.
NPG — -: do u stay up late?
EKJ: 24–7. Actaully more like 20–7.
NPG — -: good.
EKJ: y?
NPG — -: my flight gets in at 1 am
EKJ: great, ur coming 2 ny? u want me 2 meet u at 2?
NPG — -: I can send a car 4 u
NPG — -: if u like
Ekj4: yes, that would be great. don’t have a sister trying to hail a cab in crooklyn at all hours.
NPG — -: r u a sista?
Ekj4: haven’t we been over this? u will c
NPG — -: what do u look like?
NPG — -: describe urself!
Ekj4: i’m skinny
NPG — -: u eat meat?
Ekj4: on occasion
NPG — -: then y r u skinny?
Ekj4: just got it like that
NPG — -: skinny parents
Ekj4: i actually eat way too much junk food
Ekj4: i’m skinnier than everyone in my family
NPG — -: do u think we could complete an interview like this?
Ekj4: no, we cannot do the interview this way, but doesn’t matter. u’ll be here in a minute
NPG — -: y
NPG — -: then u have direct quotes

but this way is modern

Ekj4: it neesd to be face to face
NPG — -: y?
Ekj4: yes, but i have to set the scene. you get better feeling about the person that way
Ekj4: anyway, this could be aaron for all i know.
NPG — -: but this way is modern
Ekj4: yes, it is. i love to chat online
NPG — -: eye am not a liar
NPG — -: this way is cooler
NPG — -: and eye don’t get motion sickness
Ekj4: so u think we will just have some time tonight or would you be down to…
Ekj4: hang over the weekend if i need more time?
Ekj4: ur not going to be all drowsy, r u?
NPG — -: eye have 2 fly 2 oakland
NPG — -: 2morrow
Ekj4: for what? the all star game?
NPG — -: eye am never drowsy
NPG — -: yes …the game
Ekj4: u r going?
Ekj4: i watch all teh games. i love the t-wolves and kg
Ekj4: but i root for the knicks
NPG — -: eye maybe cannot go if eye go 2 new york
NPG — -: 2 much flying makes me barf
Ekj4: npg — -, u sleepin’?
NPG — -: eye wanna c the slam dunk competition up close
Ekj4: is kg in it?
NPG — -: no doubt
Ekj4: you hang with him in minn?
NPG — -: if u were me…would u fly thamuch
Ekj4: no i don’t like to fly that much. the loss of control and everything
Ekj4: y ru coming here for 1 day? to do the interview?
NPG — -: yes, eye am coming unless u allow me 2 do something cooler
Ekj4: i think u should come
NPG — -: eu
Ekj4: eu?
NPG — -: do u know what that means
Ekj4: please explain
NPG — -: this:
NPG — -: :P*******
NPG — -: me barfing
Ekj4: lol!!!!
Ekj4: why r u barfing?
NPG — -: HEY,not so loud!
Ekj4: so r u coming or not?
NPG — -: yes, eu
Ekj4: GREAT!

u type like me

NPG — -: we will call when eye ge there
Ekj4: 1derful
NPG — -: u type like me
Ekj4: now that u have my e-mail, don’t send me any spam!
Ekj4: chain letters and nonsense
NPG — -: won’t send u any mail
NPG — -: ever
NPG — -: many people use this screenname…
Ekj4: ok, npg — —
NPG — -: it’s secret, so don’t divulge it, ok?
Ekj4: oh, good so you can maintain your privacy. of course, bro
NPG — -: ever go 2 prince. org?
Ekj4: can’t say that i have. do u?
NPG — -: once or twice
NPG — -: interesting?
NPG — -: yes
Ekj4: i don’t think i would like 2 c what random people r saying about me
NPG — -: sometimes it is funny
Ekj4: taht would be strange but i guess you have become accustomed 2 it
NPG — -: yes
NPG — -: so, eye must go and pack, then
NPG — -: bye bye
NPG — -: c u 2night
Ekj4: c ya later, inshallah
NPG — -: peace

I loved these chats because they are a reminder that our legends are also real people. He loved technology, Prince started YesWeCode with Van Jones to inspire more Black Youth to get involved in tech.

I talked to Erica on the phone just two day before she passed away. I miss our regular talks and her energy but most of all I miss my friend. Prince is gone now as well, and even though he was a legend he was also a real human who loved people. He was a tech visionary who appreciated very early on how technology could bring us all together.

20 years later Prince would still reply to fans directly on Twitter (and often delete the tweets, adding to his air of mystery.) He was known to even engage in lengthy private DMs with fans and superfans.

I love what InStyle said about these Prince’s AOL chats.

I miss you two and what you brought to our lives. I’m glad we have your legacy and your work to remember you by.

Originally published at

Tech, Diabetes, Parenting, Race, Linguistics, Web, Fashion, Podcasting, OSS, Code, Inclusive, Black Hair, Phony. I work for MSFT, but these are my opinions.