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Looks like the marriage to Margaret Willard is the right one. [EDIT: Well, maybe - see next post.] She must have just been known as Myrtle:


Detroit Border Crossings and Passenger and Crew Lists, 1905-1957 about Harry H Oliver
Name: Harry H Oliver
Arrival Date: 22 May 1916
Birthplace: Guelph Ont
Gender: Male
Race/Nationality: Irish

Port of Arrival: Detroit, Michigan
Accompanied By: Wife Myrtle
Departure Contact: Father Harry H Oliver Sr
Arrival Contact: Mother-in-law Mrs Willard <<<<<<<<

Microfilm Roll Number: M1478_73

Here's the other half of that border crossing entry posted by Margee, re Myrtle:


Border Crossings: From Canada to U.S., 1895-1956 about Myrtle Oliver
Name: Myrtle Oliver
Arrival Date: 24 May 1916
Port of Arrival: Detroit, Michigan, USA
Residence Country: Canada
Age: 18
Birth Date: abt 1898
Birth Country: USA
Gender: Female
Race/Nationality: English
Record Type: Manifests
Line Number: 8

She also gives Harry's father's name as that of the "nearest relative or friend in the country whence alien came."

A tree on Ancestry says that he married Myrtle Willard 17 Feb. 1916, Ontario. This looka like the marriage but her name is Margaret:

Ontario, Canada, Marriages, 1801-1928
about Margaret Willard Name: Margaret Willard
Birth Place: Detroit, Michigan
Age: 18
Estimated Birth Year: abt 1898
Father Name: Albert Willard
Mother Name: Dessa Hillborn
Spouse Name: Henry Oliver
Spouse's Age: 21
Spouse Birth Year: abt 1895
Spouse Birth Place: Euelph
Spouse Father Name: Henry Oliver
Spouse Mother Name: Isabel Emma Fairburn Oliver
Marriage Date: 17 Feb 1916
Marriage County or District: Wellington

Harry H. Jr. and wife Myrtle entering USA at Buffalo, NY. Harry gives name of his father as Harry H., Guelph, Ontario:

Border Crossings: From Canada to U.S., 1895-1956
about Harry H Oliver Junior Name: Harry H Oliver Junior
Arrival Date: 24 May 1916
Port of Arrival: Detroit, Michigan, USA
Residence Country: Canada
Age: 21
Birth Date: abt 1895
Birth Country: Canada
Gender: Male
Race/Nationality: Irish
Record Type: Manifests
Line Number: 7

According to that 1930 census Harry H. and Anna were both aged 18 at the time of their first marriage so evidently not married to each other.

I added this to my previous thread but It doesn't really tie in with my original request, so I'm doing it as a separate thread here.
In trying to find more info on Harold Marshall Oliver, I looked at the US census to see if I could find his family. In the 1930 US census I found an H. M. Oliver with parents Harry H. Oliver and Anna Oliver, and siblings. It gives his father born in Canada and his mother born in Yugoslavia. Assuming this is the correct family I looked at the 1940 census and found his parents and one of his siblings but no Harold. I suspect he was overseas as we know he was in the Canadian military during the war and met and married his wife in England. I then looked at the 1920 census to see if Harold's parents were in the USA but the only Harry Oliver I could find was married to a Myrtle (born in Michigan). It gives Harry born in Canada, with same occupation and living with them are two of the children shown in the 1930 census. If this is the correct family and not just a big coincidence, what happened to Myrtle and when did Anna come into the picture.
Any help or suggestions would be much appreciated.