09-08-2011 14:39 - edited 09-08-2011 14:41
Can you both please right click on the others Skype name in your contact list and choose to resend the request.
If one or both of you can't do that, then please right click on the others Skype name, in your contact list, and choose "Send IM" and then send a chat message to the other.
Please click on "Contact Requests". Located under your Skype Name on the main Skype client program window.