Can you overstay to marry?

[Poy]

My boyfriend and I have been a couple for almost 3 years. I am a citizen of the US and he's a citizen of Canada. He's spent the last 6 months with me in the US (June 4th will be 6 months exactly). During this time we decided that we want to get married and after much discussion decided we wanted to live in the US instead of Canada, at least for now, because both of my parents have health issues and we'd rather be close to them. My ex has held my divorce up forever but it's officially going to be finalized on June 8th and I'll finally be free to remarry. My question is, are we better off having him go back to Canada and then file for a fiance visa or should he stay long enough for us to get married then file for a spouse visa? We certainly don't want him to get banned from the US.

[peace999]

I assume June 4 th is the last date of his authorized stay in US.

Usually , spouses of US citizens are able to adjust status to green card even when they are out of status in US.
But it does carry a small risk; he entered as a visitor, but actually had an intent to marry you ( known you for 3 yrs) and stay in US.

I think the best thing to do is to play safe and not to overstay.
If you go the fiance way, the whole process will take a long time.
If you guys are ready to get married after your divorce, and can do it in canada, do it there
and then you can return to US and file for his spousal visa in US. He can collect the visa in canada a few months later.
Or if you want to get married in US, he can return after a few months as a visitor , get married and go back.
You can then file for his spousal visa .

[Poy]

Since he already spent six months will he be allowed back in the country after just a few months?