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

Dear Hailey,

I had a best friend whose family is pretty close to my current spouse. Recently we tried to make amends and started to hang out recently. I am struggling with allowing her back into my life.

Here is the back story. I met my spouse through her as he was her brother’s best friend. Shortly after my boyfriend committed suicide, we started to talk periodically online at all hours. He eventually asked me out on a date. After our first date she found out and told her brother that he tried to have sex with her. It grew … Read more

Dear Hailey,

I am stuck! My future in laws drive me CRAZY! Me and my boyfriend decided we want to buy a house. I’m unemployed at the moment, so we decided to see if he could get approved for a loan on his own. And he did! A great amount and I couldn’t be more proud! The loan is fully in his name, but this will be our house. I’ve saved quite a bit more than him over the years for this very moment. Since I have more saved, we decided that I’d cover most of the costs.

Once we … Read more

Dear Hailey,

Many years ago my then girlfriend (whom I shall call “Tara”) knew I liked those outdoor thermometers which are in the form of a famous soda pop brand. An elderly woman who Tara cleaned for once a week had one of those thermometers attached to the side of her house. Tara gave one to me for my birthday. I asked where she got it because it looked used. She said she stole it from the elderly woman she cleaned house for.

I wrongly kept it because I was afraid if I returned it to the rightful owner I … Read more

Dear Hailey,

I’m having a big problem with my mental health and I was wondering if you could answer my question. Recently I have come into a pit of anxiety and depression. I am a gay man married to a woman. I married my wife because I thought that would convince people I am straight and they wouldn’t be homophobic towards me. However, I’ve become unhappy and I feel trapped in my marriage. I fear people will not accept me if I show who I truly am. Because of this, I am “eating my feelings” as people call it. I … Read more

Dear Hailey,

Your advice is always so full of wisdom and brilliant insight. I really enjoy your column.

I’m 40F and super close with my parents; we chat daily on the phone. My mom and dad, married 42 years, are very much in love.

However, they have a recurring conflict. Step 1: Dad does something incorrect according to Mom’s rules (for example, Dad bought a large sandwich to share, which resulted in leftovers) 2: Mom nags at Dad. 3. Dad is silent, but later explodes. 4. Mom apologizes, and soon the cycle repeats.

When my mom calls to tell me … Read more