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I've been fortunate enough to have never had to write a No Rec, as yet. I'll share the hardest ones I ever had to deal with from an advisor standpoint. In one of my first years advising, an in-house active's younger sister was going through Recruitment. I received No Recs from 2 highly respected and trustworthy alums, women I knew personally who were also well respected in the Inat'l org. Seems that in the year since the older sister left for college her younger sister had ... well let's just say went completely wild. I guess she managed to hide it from the older sis.
I had to inform the older sis that we would not be extending her a bid and would actually be dropping her before Pref. (Normally we would drop No Recs even earlier, but we wanted to extend as much courtesy to the older sister as we could.) Older sis blew up and ended up turning in her pin to protest.
I later heard through the grapevine that the 2 sisters got an apartment together. Older sis then discovered younger sis was no longer the little angel she thought. She ended up regretting her decision to resign.
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