It sounds like both of you are putting too much pressure on finding the ideal situation. Sure it might happen, but you can't expect it. I would either forget the whole idea for now and focus on your own relationship, or you both go out and find people to date. Having him sit at home while you go and hopefully find someone for him to be with too is too much pressure. All that unnecessary energy will be following you around on your dates and there is no need for that.
Don't fight against the existing model, create a new model that makes the old model obsolete.