10pm email trouble

Scene: It's 10pm on Sunday night and I am sitting in the bathroom streaming Dragonball Z to my Nexus One from my PC. Suddenly the phone rings.

Me: Uh, hello?
TNolan: Hey what are you doing?
Me: umm, nothing...
TNolan: Hey I just sent an email and John didn't get it.
Me: Ok, what did you do?
TNolan:  I sent it but he didn't get it.
Me: What are you trying to send?
TNolan: A picture.
Me: What are you using to send it?
TNolan: Outlook:
Me: Didn't we talk about you not using Outlook?
TNolan: It was from my work account. I sent it but he never got it, but I got it when I sent it to myself.
Me: So you sent it to your self at the same time?
TNolan: No, after he didn't get it I forwarded it to myself.
Me: Ok, look in your outbox, do you see the email you tried to send?
TNolan: No, there is nothing in the outbox cause I deleted it.
Me: What about the sent folder?
TNolan: No.
Me: What about the drafts folder?
TNolan: No, I sent it and he didn't get it. I don't know why his gmail isn't working.
Me: I'm gonna hang up and send him a test email now.
TNolan: K

Email to John: Test- reply if you get this.
(Two minutes later)
Email from John: Yep, I got it.

Executive decision made to not call back until morning.