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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.