Dear Hailey,

I am a 31-year-old woman. My best friend only seeks out people who are successful in a very conventional sense- Harvard graduates, Google/Microsoft employees, and those running successful businesses. I find it very limiting and a hindrance to building healthy relationships.

Being the CEO of a startup, she, I think, embodies the corporate culture that hates any signs of “weaknesses” and has less time to delve on the so-called negative emotions like fear, anxiety, depression etc. We have really fun time together but whenever I am down with any of these emotions, I feel like she tries to … Read more

Dear Hailey,

I have been in a relationship for almost two years now with an amazing man. There’s ups and downs of course but it’s when things go down we really struggle. I’ve tried so many different ways of communicating to him my feelings of loneliness and unimportance (especially using “I” statements being careful not to call out any of his flaws or wrong doings) and he has a very hard time being receptive and tends to get extremely defensive and make the whole problem about himself rather than acknowledging my needs. He often is disconnected from reality and likes … Read more

Dear Hailey,

I have severe social anxiety and it makes it difficult to work. I have been able to manage well before because I have always loved my jobs and what I do. However I recently started a new job after losing my last due to COVID. This new job makes me feel overwhelmed and is deteriorating my mental health. Should I stick it out or take the risk of being unemployed and quit? Thank you so much in advance for your advice!

Mayla

Dear Mayla,

I’m sorry to hear that you lost your job due to COVID. It’s been … Read more

Dear Hailey,

I feel so horrible. My sister is always yelling at me and being in my room – her excuse, ‘ The cat is in there.’ I ask her to get out of my room, ‘Get out of my room. This is my room, and you have yours. Please get out.’ But she starts raising her voice, yelling at me, and acting like I said the most insulting thing in the world. So then she starts screaming at me- she’s 10 by the way and I’m 13, acting like I never spend time with her. I don’t spend my … Read more

Dear Hailey,

My husband’s ex-wife is planning a Christmas gathering with more households and people than recommended during COVID-19. The day after, my husband still plans on his daughter coming to our house for a few days. I feel this is putting my safety at unnecessary risk. I plan on staying somewhere else for 2 weeks to quarantine from both of them. I am angry at the selfishness and disrespect beyond explanation.

I have kept that to myself and am doing what I need to do for my wellbeing. An argument wouldn’t be worth it. What I don’t know is … Read more

Dear Hailey,

I have been dating a widowed man for almost 8 years. I moved into his family home (at his urging) 3 years ago. He is a father to four adult children (ages 21-30). His 30 year old son lives in the basement and is under/un employed at this time. He may be addicted to video games, and often is up all night playing them, then sleeps until late in the afternoon. Prior to COVID he worked part time (20 hours a week). His father pays for his auto insurance and his cell phone, and sometimes charges his $150/month … Read more

Dear Hailey,

I’ve always prided myself on my ability to give advice, when it’s asked for, to my friends and family. I enjoy helping my loved ones out when they’re having issues. The problem is that my sister comes to me several times per week for hours long sessions that exhaust me. I love my sister and want to help her but I always end up feeling drained after consoling and advising her. 

A little backstory, I am the middle child of 3. I have an older brother and a younger sister. I am 5 years older than my sister … Read more

Dear Hailey,

I have been feeling like I’ve been at a cross-roads for about 4 months now. I’ve talked it with my therapist and all of my friends and family and nothing is helping me find an answer or even feel better about the situation. 

When I was in high school there was this guy that I was absolutely in love with. We never dated, or even did anything romantic whatsoever, I just had an insane crush on him for my entire Junior and Senior year of high school. I am 90% sure he liked me back too, but we … Read more

Dear Hailey,

A person I know who is more of an acquaintance than a close friend is giving away items that she owns. She plans to move to a smaller place and wants to downsize. She had many boxes of books that she didn’t want anymore. I told her I like a certain genre of books and asked if she would put some aside for me. So she gave me a box of books, mostly paperbacks. She took other boxes of books to the curb so the trash collectors could pick them up.

The problem is that the box she … Read more