I've been on Hip for a little while now, but it seems I can't start a personal message with someone. I can receive them just fine. I just can't send the first message if they haven't messaged me. Is this because I'm still considered new?
Could be. You may want to post in the User Support forum about this. The easiest remedy is to just keep posting. If you want to get in touch with someone in particular, you may be able to leave them a visitor message, or make a post on a thread that you know they are on asking them to message you
