My brother -in-law hates flying.
The last time he flew was coming back from Spain to get married in 1973. Last summer my wife, sister and brother-in-law all came over to the airfield so I could show off the group aircraft & take my sister flying, for she has no qualms.
I preflighted the aircraft and said 'OK, whose first?' To my intense surprise, Charlie said 'OK - I'll go, but only a quick one'.
So we strapped in and took off, for just one circuit. Now I can't say that he loved it, but it gave him the confidence to get on an aircraft and fly to Spain later that year.
So I've taken my drinking buddy and Mother-in-law up for their first ever flights, re-introduced B-i-L to flying and was able to fly my aged mother over her home before she got too infirm.
My one regret was that my father never lived long enough for me to take him flying, but as he worked at North Weald during the war, where I now fly from, I'm sure he won't mind.