Not entirely sure, but Him being illegal in US, will cause issues for Him in here as well. If one has spent more than 6 months in a country other than their homeland, they will need Police Certificate from that country. In this case, our brothers down from 48. parallel, he would need to send a set of fingerprints (say from RCMP, ~68 bucks) to West Virginia FBI Headquarters for criminality checks. Now he is not a person of status in there, so that poses a problem.
We live in America, where everyone is out for their own gain, there is nothing personal in this, it is just a business.
Now it might seem silly, but why don't you 2 lovebirds go to Mexico, marry there and then do the outland process, there is no way around it anyways. Just be brutally honest with CIC and you guys just might make it, God Bless.