Why does "enjoy" (almost) not have a causative sense?
Solution 1:
The book "Word Origins" (by John Ayto) states that the verb is used intransitively in the past but it is predominantly used in transitive sense today. Also, it mentions the Yiddish influence on the verb:
Then I did a research about the Yiddish influence and found this New York Times article that explains the origin of "Enjoy!":
In his 1986 book, "Yiddish and English," Random House lexicographer Sol Steinmetz cites this 1968 quotation of furrier Jacques Kaplan by Marylin Bender in The New York Times: "It's a dancing over the volcano attitude, an enjoy-enjoy philosophy." That reduplication is typical of Yiddish -- Es, es means "Eat, eat" -- and the friendly command of Enjoy! comes from Hob anoe , a Yiddish phrase derived from the German hob , "have," and the Hebrew hanoe , "enjoyment."
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The earliest example of the absolute use of the transitive enjoy comes from an essay by English author John Ruskin in "The Eagle's Nest," in 1872: "It is appointed for all men to enjoy, but for few to achieve."
Solution 2:
OED lists the causative sense but as obsolete:
†2.a. trans. To put into a joyous condition; to make happy, give pleasure to. Obs.
?1488 Caxton tr. Laurent Ryal Bk. sig. Cj, For to gladde and enjoye the people.
c1500 Melusine (1895) 150 Whos taryeng enjoyed her moche.
1502 tr. Ordynarye of Crysten Men (de Worde) iv. xxvii. sig. ii.iiiv, That it hym may enioye and recomforte in his spyryte.
1610 G. Markham Maister-peece ii. li. 107 No meat will enioy or do good vnto him.