John W. Orear was a son of Robert O’Rear and followed his father to Orearville, Saline County, Missouri. The following very gracious letters recount his courtship while a young man in Kentucky.
Mount Sterling, September 3rd, 1836
Miss Elizabeth:
You may be surprised on receiving a letter from me, but let me assure you I write this letter with the most honourable views. I trust I may expect your pardon should the contents not be perfectly congenial with your vies in making you a proposal. I hope I am not trespassing on a heart already bestowed on some favoured object. In making my remarks I design being plain and pointed. I have to lived to an age which in my judgement should determine my regular course through life and to do this I lack one thing, that is your consent to spend the remainder of your days with me. You now fully understand me. My home is in Mountsterling where I expect to live and die. Should you consent to crown my wishes let me assure you my aim will be to tender you agreeable. This is a matter for life, weight it well. My friend D. Hiram will hand you this letter and wait your reply which I hope will be soon as I intend starting east as soon as my brother’s health gets better and would be happy to have you in company. On reading this letter your mind may be brought to a conclusion. If it should not be favorable, be so kind as to hand this back to my friend Hiram who will again return it to me and the matter perfectly at an end.
I am ever your friend,
John W. Orear
Mt. Sterling, September 6, 1836
Mr. Orear,
I received your very unexpected letter by our friend Mr. Hiram, the contents of which I read with surprise and with the most serious attention. The proposal you made me is expressed so honourably and sincere that I consider it my duty to act with decision. Having given the matter due reflection after my long acquaintance with you and the high opinion I ever have entertained with you, I am now prompted to accept your offer, believing I will not regret it. The kind invitation you gave me to accompany you in your trip Eastward, could I accept it, would be to me a source of pleasure, but the time probably is too short for me to make necessary arrangements, and you will please excuse me.
Your sincere friend
Elizabeth Challen