Very cool!
I think the ability to set the day of week and time of day to do the matchups would be on my immediate wishlist, so people would get the message when they are likely to be around and ready to reply.
And I think multiple text templates would be even better, to keep the bot from repeating itself each time it sends out the scheduled messages, and allow varying the number of people in each message. So you could mingle with just one person one month, then get a group message with 3-5 people the next and so on accompanied by a message template that matches the number of participants.