ArcaMax

Dear Annie: I work remotely and rent a small guesthouse on a property owned by a retired couple, "Tom" and "Linda." They live in the main house and are kind, but recently their friendliness has crossed into something more intrusive.

At first, it was small things; Linda would wave and come chat while I was outside on a break, or Tom would ask ...Read more

Dear Annie: My sister, "Jenna," is 38 and recently started selling handmade candles online. I was excited for her at first; it's a big step to start your own business. But now, every conversation somehow turns into a pitch. She'll bring candles to family dinners and "gift" them, only to follow up later asking for social media shoutouts or ...Read more

Dear Annie: I'm 65 years old, and after years of focusing on everything and everyone else, I finally feel ready to date again. The only problem is -- I'm not sure how to go about it, or if it's even realistic at my age.

I'll be honest: I have not been the best judge of character in the past. That makes me extra cautious now, especially when ...Read more

Dear Annie: I had my kids in my early 20s, which felt right for me and my husband at the time. We live in New York City, where most parents we meet had children much later in life. At school events, playdates or birthday parties, we're often the youngest parents in the room -- sometimes by more than a decade.

While everyone is polite, I can't...Read more

Dear Annie: I'll be starting college this fall, and while I'm excited to grow academically, I'm also looking forward to making new friends and maybe even finding a boyfriend. But I already know one thing: I don't plan on sharing many details about my romantic life with friends -- if I mention it at all.

Here's why: I've noticed that when ...Read more

Dear Annie: I'm 45 and trying to move forward after the end of a 15-year marriage that left me emotionally and financially depleted. In my early 20s, I was an ambitious, college-educated overachiever who fell in love with a charming, carefree man. He had no real goals, had flunked out of college and was working part-time in fast food. But I ...Read more

Dear Annie: My sister lives across the country and recently lost her husband. She doesn't have much of a support system nearby, and she's not in good health and can't get around well at all. She can barely take care of herself, never mind her little dog. Her home has serious issues because it's been poorly maintained. I haven't been able to go...Read more

Dear Annie: I have a frustrating problem with my mother. I'm 40 years old, but she still treats me like I'm a teenager. She expects me to answer every call immediately and freaks out if I'm unavailable, often roping in my cousin to text me if I don't respond since my mom doesn't know how.

This has been going on since I was a teen. When I was ...Read more

Dear Annie: I need some advice. My son got married three years ago to a woman we didn't know about. He never brought her over to introduce her to us. Didn't even tell us he got married. He stopped speaking to us.

Then, when my husband died, my son asked if I got any insurance money. That took me back. I don't see him anymore unless he needs ...Read more

Dear Annie: My husband has been coaching our 8-year-old son's soccer team this season. At first, I thought it would be a great bonding experience for them. Our son is an active, sweet kid who used to spend hours in the yard practicing his kicks and counting down the days until the next game. But now, that excitement is gone -- and I think I ...Read more

Dear Annie: I am a 60-year-old divorced mom with three grown children in their 30s. I have spent most of my adult life putting my family first, especially after my marriage ended more than a decade ago. I raised my kids mostly on my own, worked full time and never really dated seriously again. Part of that was fear, and part of it was being ...Read more

Dear Annie: I recently hosted a small dinner party at my home for a few close friends -- just six of us, gathered around the table for what I hoped would be a relaxing evening of good food and conversation. I spent the day preparing a nice meal, setting the table with care and making sure everything felt warm and welcoming. But one guest, my ...Read more

Dear Annie: My daughter recently got engaged, and while I want to be happy for her, I have serious concerns about her fiance. He's moody and dismissive, and I've seen him speak to her in ways that feel demeaning. She brushes it off and says I'm being overly sensitive. I don't want to ruin our relationship, but I'm struggling to stay silent ...Read more

Dear Annie: I feel like I'm in a toxic relationship with my roommate. We're both older and used to be good friends until we got a place together. I quickly realized she has somewhat of a hoarding issue and a habit of starting projects she never finishes.

I work two jobs and am gone from 6 a.m. to 6 p.m. or later. Meanwhile, she collects ...Read more

Dear Annie: I've been dating my boyfriend, "Dylan," for almost two years. He's perfect except for the fact that he avoids conflict like the plague. If I bring up anything even slightly uncomfortable -- like that something he said hurt my feelings -- he either shuts down, changes the subject or tries to make a joke out of it.

At first, I ...Read more

Dear Annie: I have recently gone through a friend breakup with a friend we will call "Elizabeth." When I first met Elizabeth, she was pregnant with her first child. After about a year, we became very close friends, and she had a second child. After the second child was born, I offered to go to Elizabeth's house once a week to play with the ...Read more

Dear Annie: My sister and I were inseparable growing up. We talked every day, shared everything and supported each other through some tough times, including the death of our dad five years ago. But ever since she started dating her current boyfriend about a year ago, things have changed in a way I never expected.

At first, I tried to be ...Read more

Dear Annie: Lately, I've been finding myself feeling unexpectedly down. My three kids are all growing up so fast -- one just graduated college, one is starting a new job out of state and my youngest just got their driver's license. I'm proud of them, of course. They're kind, capable and finding their own way in the world. But I feel like I ...Read more

Dear Annie: I've been married to a wonderful man for over 10 years, and during that time, I've grown to love his son as my own. My stepson, "Brian," is now 28 and has struggled with drug addiction for most of his adult life. We've helped him through multiple rehab programs, paid his rent when he's been evicted and even bailed him out of jail ...Read more

Dear Annie: I have been married to my husband, "Dave," for 22 years. We met in college, and back then he was funny, attentive and full of life. We built a life together, raised two kids, managed careers, took family vacations, hosted holidays and always tried to be a united front, even during hard times. I have always thought of our marriage ...Read more