Asking a legitimate question will certainly not hurt an applicant in any way. One can certainly contact the admissions office anonymously to ask the question if one is concerned.
To that end, I will also say that unless the kid has attended a college fair (or similar venue) and the rep handed the kid a card and said “Contact me with any questions you have,” questions should be directed to the general admissions office phone number/email, not the rep, even if a college published its entire employee directory.