I’m really worried about a female friend who flirts continuously and gives her phone number to any man she meets at the grocery store, gas station or wherever. These are not quality men. She’s desperate, and so are they. I met her latest at her Christmas party. She says he makes her laugh and that they are both interested in the healing arts. She was in his bed on their first date. The guy is creepy. At the party, he was full of loud stories that were so obviously lies that people were embarrassed for him. She just beamed. He later asked if I wanted to smoke weed with him. She thinks he’s in rehab. How do I tell her that he is not what he seems? She has really low self-esteem and takes advice hard.

There’s a difference between telling her that he is not what he seems and giving her advice. The only words you need to utter are: “[His name here] invited me to smoke a doobie with him at your party. Imagine that! I recall you saying he’s in rehab. Please be careful. I really care about you.”

If she presses for advice, or you can’t control your desire to give it, digest the wisdom of the ancient sage Rabbi Akiba ben Joseph, who wrote, “Pointing out someone’s shortcoming or error should not be a chance for insults or a sense of superiority. It should not become an opportunity to humiliate or gloat. Instead, a rebuke, if properly intended and given, becomes an act of affirmation and love, an affirmation that the person is worth the effort in the first place, and a faith that he or she remains capable of improvement.”

You also might invest in the insights of Rabbi Bradley Shavit Artson of the University of Judaism. “We all blind ourselves to our own faults and to those aspects of reality we don’t want to see. Each of us depends on the caring of others—their courage to articulate disappointment in our action—as the indispensable prerequisite to self-improvement and refinement.” In order to ground yourself in the love and humility required for giving advice, you must admit whether you are projecting any of your own issues onto your friend. For example, how is your self-esteem in romantic relationships? How is it when you’re in the company of other women? How do you respond to advice? Talk to your friend only after you’ve had an honest talk with yourself.

My fiancee and I work together. A female co-worker got me drunk at the company Christmas party and seduced me. When I sobered up, I made her promise not to tell. On New Year’s Day this co-worker saw my fiancee in the company lunchroom and said, “You are so lucky! Bobby is a hot lover!” My fiancee came screaming into the warehouse where I work. I calmed her down by reminding her that this co-worker is nuts, but now my fiancee thinks the co-worker lied. I’m scared she’ll find out otherwise before the wedding. What should I do?

Take responsibility for accepting those drinks and for sneaking out to the car to have sex while your fiancee was inside singing perky carols with co-workers. Be an adult. Tell your fiancee what really happened (the version in which you are 50 percent responsible). She deserves to know what you’re really like, and it’s better if she learns from you than from the woman you chose to have sex with or from half-whispered rumors around the office. If your fiancee decides to stick with you, get yourselves to a marriage counselor so this little drama doesn’t repeat itself.