All perfect praise be to Allaah, The Lord of the Worlds. I testify that there is none worthy of worship except Allaah, and that Muhammad is His slave and Messenger.
The words that were uttered by your friend are considered conditional divorce. The majority of the scholars are of the view that the divorce that is suspended on a condition becomes effective when that condition takes place. Therefore, if his wife does the thing upon which he suspended the divorce, then the divorce takes place, and it takes place as one divorce only. For more benefit, please refer to Fataawa 117760, 139750 and 99468.
If the condition upon which the divorce was suspended takes place, then this condition is no longer valid for another time [i.e. it applies once only] and if the wife does it again during the waiting period or after it, then divorce does not take place another time on her as it has already taken place once and it is no longer valid, unless the condition is said with a wording that necessitates repetition, like: “…every time ….”, so if the condition is said with these words (and the like) then the divorce takes place every time she does the thing upon which he suspended the divorce because the wording “every time” implies repetition.
Al-Hattaab from the Maaliki School of jurisprudence, said: “If one makes an oath not to do something and then he does it, then he broke his oath one time by doing it, so he does not have to expiate for it after that unless he had intended the repetition of the oath every time he does that thing, in which case, the oath takes place another time.”
Finally, it should be noted that a Muslim should not borrow money without a need as this makes his liability occupied by the rights of people. Indeed, borrowing money is a serious matter. The Prophet said: "The soul of a believer remains hanging with his debt till it is paid off (on his behalf after his death).” [Ahmad, Abu Daawood, At-Tirmithi, An-Nasaa’i and Ibn Maajah] The Prophet also said: "Every sin of the martyr is forgiven except debt.” [Muslim]
Allaah Knows best.