In preparing for a trip to the Shenandoah Valley later this year, I am again delving into the FRYMAN family. I just now came across your post. I am hoping you're still researching and find this.
There certainly is information that tracks, but the details are off. Allow me to share what I know in a bit more detail.
Marriage bond in the amount of $150 entered into by George FRYMAN in Shenandoah Co., Virginia 07 Jul 1804. "The conditions of the above obligation is such, that wheras there is a marriage shortly intended to be solemnized between the above bound George Fryman and Mary Cunningham (widow)...." Bondsman was Henry HOUSHAW or HAFUSHAUSE. This transcription was sent to me some years ago by a FRYMAN descendant.
A THOMAS CUNNINGHAM took out a marriage bond in Shenandoah Co., Virginia on or before 21 Dec 1795. His bride was to be one Mary LICHLITER, and John LICHLITER was the bondsman. I have not been able to learn the relationship of Mary to John.
In order for Mary CUNNINGHAM to have been the widow who married George FRYMAN, Thomas would have had to have died sometime between 1795 and 1804. Based on your information, one Thomas CUNNINGHAM died 1797, leaving a widow and child who may have been born posthumously.
It appears there may have been at least one other Thomas CUNNINGHAM who lived in the county at roughly the same time. Per a transcribed Shenandoah County, Virginia Minute Book (1791-1796): 27 Dec 1792 "Overseer of the Poor Dist. #1 to bind Thomas Cunningham, orphan of Thomas to Peter Hoshour to learn the trade of tanner. He is 5 yrs old Jan. 15, next."
This CUNNINGHAM family appears to have lived in the same Poor District #1 as Charles FRYMAN, father of George FRYMAN. 10 Mar 1795: "Overseer of the Poor Dist. #1 bind Betsey Fartig, a base born child of Betsy Fartig to Charles Fryman. She is six yrs old May 1, next."
Some of the FRYMAN family removed from Shenandoah Co., Virginia to the vicinity of Belmont Co., Ohio before 1809. Woodsfield, Ohio is in Monroe Co. today, adjacent to Belmont.
Mary Cunningham FRYMAN lived to age 83/84. She can be found on the 1860 census in Thompson Twp., Delaware Co., Ohio living with her son Frederick FRYMAN and his wife. She is buried in Shoup Cemetery in Thompson Twp., Delaware Co., Ohio. She presumably died in the same township.
Do you have additional information on any of the parties mentioned?