Ben Claassen III (For Express)
Express Advice Columnist

Don’t miss the next live chat: Dr. Andrea Bonior, a licensed clinical psychologist who has been helping readers with Baggage Check since 2005, hosts a weekly live chat at washingtonpost.com on Tuesdays at 1 p.m. She discusses her recent columns and answers any questions you may have about relationships, work, family, mental health and more. Join or read Dr. Andrea’s latest live chat here. This week, Dr. Andrea welcomes psychotherapist Lori Gottlieb, author of “Maybe You Should Talk to Someone.”

Q. I have a friend who complains and complains about how unsatisfying his dating life is, but he only goes for the most beautiful of women, and he has an inflated idea of his attractiveness. He is constantly criticizing average-looking people on dating sites while getting angry that the most attractive people won’t respond to him. I find this so frustrating. Since I am a woman, I don’t want to get into a conversation about attractiveness because I feel like he will get defensive and say something hurtful about my own looks. But I also want him to have a reality check.

So I went from empathizing with this guy to thinking that he is a superficial, condescending and insensitive person who deserves to be sentenced to a week’s worth of bland couscous. (And I always try to err on the side of empathy!)

His go-to defense in a conversation about how he sabotages himself will likely involve criticizing your looks? Wow. This sounds less like the typical “I might think I’m hotter than I am — I deserve a gentle reality check” and more like a situation where someone’s narcissism is laced with cruelty. I would focus on that, more so than his objective ranking as a Handsome-or-Not Man. Tell him that when he criticizes average-looking people, it makes him seem shallow — and women don’t happen to love that. Convey to him that if he views human beings as products of their facial symmetry or waist-to-hip ratios, he is bound to miss out on real fulfillment. Honestly, if he doesn’t get these concepts, it seems like a friendship whose “so frustrating” status is unlikely to change.

She’s back home but so far away

Q. Our daughter just came home from her first year of college and she seems different. I know that college is a big time of growth and development and I don’t expect her to have stayed the same, but she seems more preoccupied and quiet and private, and she has less energy. I go back and forth between thinking that my expectations are too high and maybe she is just getting space to become her own person versus thinking she might be depressed. I don’t know how hard to push to get her to open up to me.

Your sensitivity is commendable, but there’s a huge difference between pushing her to open up versus doing absolutely nothing. And within that middle ground is listening, connecting and reflecting. So, don’t interrogate, but just reach out a hand and an ear. Think of activities she might enjoy doing together to get her out of her room and make your conversations less forced. Make it clear you want to listen and get to know her life as it is now, and let that help you determine what’s happening. She may be depressed or even traumatized about something, or she might just be a college kid who amassed a big sleep deficit and is also trying to figure out who she is now if she’s not just somebody’s daughter (an affliction that is totally normal and healthy).

Send your questions for Baggage Check to Dr. Andrea Bonior at baggage@wpost.com. She may answer them in an upcoming column in Express or in a live chat on Tuesdays at 1 p.m. at washingtonpost.com.

Read more Baggage Check:

I’m afraid my wife will need even more ‘me time’ if we have a baby

Is it OK that I like my girlfriend’s kids more than I like her?

My co-worker is obsessed with my boyfriend but doesn’t seem that interested in me