When did Cicero and Pompey first meet?
Biographies in my library are either silent (Gelzer), or report it happened during the Social War, when in 89 they were both on Gn. Pompeius Strabo's staff. Pat Southern in Pompey the Great even then hedges and writes that they may have met.
Allen M. Ward, in The Early Relationships between Cicero and Pompey until 80 B. C., Phoenix, Vol. 24, No. 2 (Summer, 1970), pp. 119-129 (JSTOR, limited access), argues that it could have been earlier than that:
THE TENDENCY HAS often been to ignore or discount the possibility of any personal contact between Cicero and Pompey in their early years. Richard Johannemann vigorously maintained that Cicero first came into personal contact with Pompey only in 71. A re-examination of the evidence will show, however, that Cicero and Pompey probably did have contact with each other well before 71 and possibly from a very early date.
Ward points to Cicero (Fam. 1.9.11. to P. Lentulus, March 54), where he writes: “[one] whose public claims I had conspicuously supported from my youth upwards” (ab adolescentia). Since young men starting their career on a general's staff were usually chosen amicitiae causa, Ward argues that “it is possible that they had already met through some connection between their families, and would be impossible to deny some personal contact between the two young man at that time.”
They were exactly the same age, both came from municipal families who were equites, and they lived in the same neighborhood in Rome.
After the war, so Ward tells us, it is possible to demonstrate, through investigating mutual friends and associations, that Cicero and Pompey were well acquainted with each other during the rest of the 80s, and he proceeds to provide proof. This includes Cicero's friendships with relatives of Pompey, two of whom were later Pompey's legates. One of these, Pompeius Bythinicus, died with Pompey in Egypt according to Orosius (6.15.28). There are also several Terentii mentioned, as well as Q. Mucius Scaevola, whose daughter Mucia was married to Pompey, and the Caecilii Metelli, two of whom were Mucia's half-brothers of course.
In any case, it's an interesting argument.
Colleen McCullough, in The Grass Crown, has their acquaintance begin in Strabo's army.