Dear Hobie & Monk,

I have a friend from college whom I like a lot and see socially, but she has some personality issues that make it difficult for her to stay in any one job for very long. Her numerous firings in the last couple of years are not on her resume. Now she is interviewing for a job with a CEO whom I’m also friends with, and almost daily my college pal asks me to put in a good word for her. Of course, recommending someone I know to be a less-than-stellar employee would not be good for my professional reputation. What to do?

– Unwanted reference

Monk: Your college pal is not being fair. Maybe the personality issues that have made it hard for her to keep a job also make her oblivious to taking advantage of an old friend.

One approach to this tricky situation is to have her identify the untenable discrepancy between what she knows to be true (she knows she has a dodgy employment record because she omitted the bad stuff from her resume) and what she wants you to do (lie) by asking her what she thinks is a fair assessment of her work history.

Maintain an interested and friendly tone and listen carefully, because her response will be illuminating, hopefully, for both of you. She will: A) give an accurate picture of her past performance and admit that she wants you to recommend her anyway; B) pretend she has a stellar past and act like you’re an idiot for asking; or C) admit to, but minimize the relevance of past firings to the current situation.

Her answer will help you understand how she thinks about herself and your friendship, but your answer will be the same regardless: If you speak to your CEO friend about your college friend as a potential job candidate, you will give your version of a fair assessment of her work history. You’re a friend, but you’re an honest friend.

Hobie: Monk is right, but you can choose to handle the situation with a lighter touch if having this weighty initial conversation with your friend seems too heavy-handed. Yes, it’s of course inappropriate for her to put you in an awkward position. But given that, you should feel completely justified in laughing it off and saying, “Oh, I’ve learned never to mix business and friendships — congratulations on getting the interview. Tell me how it goes.”

If done quickly and confidently, it may surprise or even offend her, but imagine what mental acrobatics it would require on her end to keep pushing it once you’ve drawn a line in the sand. And if she does, then I’m guessing you’d feel much more comfortable taking it to Monk’s level and having a quiet, more serious conversation with her about what you’d actually have to pass along to your CEO friend.

Hobie and Monk are two Alexandria women with husbands, children, dogs, jobs, mortgages, unmet New Year’s resolutions, obsessions with impractical shoes, English novels … and Ph.D.s in clinical psychology. Their advice, while fabulous, should not be construed as therapeutic within a doctor-patient context or substituted for the advice of readers’ personal advisors.