I was thinking something along the lines of large age gap and possible restricting it to same or differing genders. If it were the same gender, the elder could talk the younger through some issues they might be having. If differing genders, the same could be done but through a different lens.
If you were to go random I would think the opposite would be a better idea. Personally, as a college student in his early 20's, I don't know what I would write or how well I relate to someone who is in his or her 30's or 40's. I feel it would be more rewarding if it were with someone of my own age, though not necessarily my own gender mind you. I also feel like since the average age on a site like Hubski tends to skew low there may not be enough older candidates to match up with young ones. So basically I think I now support a systematic system based on pairing people of the same age, irrespective of gender.
Aye, and I imagine that Hubski's population - which is probably heavily male - would not allow for sorting based on gender either.
I too am a 21 year old college student, which is why I like the idea of the pairing. I think that there are a surprising amount of elder Hubskinites. Even if someone in their 30s-40s were to correspond with someone like us, I think that that'd be fairly rewarding as well.
Well that's just my two cents. Whatever you decide to do I'll still be glad to participate.