My friend’s brother thinks I’m hot and wants to hang out. He’s a senior (we’re in high school) and will be going to college out of state. I want him to be my boyfriend, even though I know I’ll be brokenhearted when he leaves. My friend, I’ll call her Lily, doesn’t care if her brother and I get together. But their mom is totally against it. She basically told Lily that our friendship will be over if I date her brother. She said that Lily will be caught in the middle, and forced to take sides when her brother and I argue. She also said that Lily will always feel left out. Then the mom told her son that he was mean to take away his little sister’s friend. I don’t know where she gets off saying this stuff. Lily’s brother blew his mom off, but Lily is freaked out. I want Lily to be my friend and I want to date her brother. What should I do?

Project yourself 30 years forward and imagine being the mother of two teens who face the situation you’ve described. Doing so will help you understand the fear motivating your friend’s mom. She may believe herself unskilled at helping her daughter navigate emotional uncertainty and, so, wants to avoid it. Or she may think mothers should protect daughters from uncomfortable feelings, rather than be models for how to handle discomfort. She may also be afraid of conflict between her daughter and son because of the resulting stress on the family. Any one of these scenarios is possible, but there’s no guarantee that any will actually happen.

It’s more likely that your friend’s mom is an adult burdened by unresolved drama from her own past relationships. Most of us are in denial about our own shadow, the aspects of ourselves that we find unacceptable, embarrassing and even shameful. But you can’t counsel your friend’s mom to process her fears. She’s an adult and unlikely to listen to you. Plus, she’s convinced she must intervene to avoid a crisis and can’t see that she’s a crisis creator.

My suggestion is to hang out in a group that includes your friend and her brother. It will give you a chance to get to know each other better. By hanging out along with other friends, you can discover whether you’re right for each other while also showing his mother that her fears have nothing to do with you, Lily or her brother.

I’ve been dating a new man and I keep noticing one thing I’m uncomfortable about. He is consistently overly attentive to waitstaff in restaurants, especially if the servers are women. I don’t always get the feeling that he is attracted to these women, but I find the intense attempts to connect with them uncomfortable in some weird way I can’t quite pinpoint. Any insights?

Is he needy for attention and always in search of a new audience? Is he trying to impress you by being overly considerate to service staff? Or is he simply a kind person? The only way to really know the answer is to ask yourself why his behavior makes you uncomfortable. Hey, maybe you’ve been cheated on and are extremely sensitive to any shift in a date’s attention. After some self-examination, I suggest that you reach beyond your comfort zone and try it yourself. Treat servers like family and friends and see how your date responds.