“My Childhood Friend Won’t Leave Me Alone!”

I am in my early thirties, married, and a new mother of one. A couple years ago, a few close friends and I started playing tennis one evening a week. We all loved it and it gave us a chance to catch up between busy schedules, work, etc. When I found out I was pregnant, I chose to quit tennis and my friends all kind of stopped as well. Recently, I asked if they wanted to pick up where we left off and they did. My friend Melissa got word of this, which has been causing me stress. She and I grew up together and were best friends in high school. We…

“How Can I Deal with My Entitled Mother-in-Law?”

My mother-in-law is your stereotypical difficult MIL: – She behaves badly when things are not about her or do not go her way. She had a wedding tantrum when she felt she was not being treated specially enough as mother of the groom. In every photo of her she is scowling. Whenever she talks about the wedding week, she refers to her side trip to the Grand Canyon as the highlight of her trip. – She is a manipulative crier and will start crying when she feels she is being “attacked” (i.e. anyone trying to speak to her about her behavior). – She is incredibly self-absorbed and controlling. – One day before…

“My Girlfriend Isn’t Welcome at My Family’s Christmas”

My ex dumped me about three months ago. Within a month, I started seeing another girl who understood and respected my situation, and we have taken things slowly. (I’m 29 and she is 27, fyi.) All my friends and family thought it was way too fast to find someone else, but I have a connection with her. We are now officially together and I’m extremely happy. We both live at our respective parents’ houses, and while her parents have been nothing but welcoming, my parents don’t want to involve themselves — or see anyone else in my family involved — with my current girlfriend. I asked if she could come to our…

“Who Should Keep My Engagement Ring?”

My boyfriend, Rick, and I are having a disagreement about engagement rings that I hope you can help with. Rick’s ex-wife, since their divorce four years ago, has pawned her engagement ring because she “needed” the money, despite everything she got from their divorce settlement. Rick is very disappointed because he spent a lot of money on the ring and because he thought she would have given that ring to their oldest child and only daughter. Now he wants to get me a ring and get married, despite the fact that it is very early in our relationship, but we disagree on what to do with the ring after I die or…

“Will His Estranged Mother Ruin the Christmas Party?”

My husband has been estranged from his mom for about three years. The reason is a really long story, but we think she has borderline personality disorder and she can’t take responsibility for her actions. He has no interest in reconciling with her at all. We just got invited to a family Christmas get-together and she, too, has been invited. My husband doesn’t have much family so I’m sure he’d love to see them, but I know he absolutely doesn’t want to see his mom. They don’t really do get-togethers like this, so it’s not like we could just see them all another time. His mom has only seen our older son…

“I’m Embarrassed That My Daughter Calls My Boyfriend ‘Stepdad'”

I’ve been living with my boyfriend for a year now, and I have a daughter, Carol, from my previous marriage. Lately, she’s been insinuating that he’s her stepdad. I’m very embarrassed because he’s never brought up marriage. I feel that unless you’re engaged or married, your kids should refrain from calling your partner stepdad or stepmom. Should I tell Carol to stop saying that? I don’t want my boyfriend to feel pressured. It makes me uncomfortable. — Too Embarrassed to Pressure Him

“My Boyfriend Is Unemployed, Lives With His Parents, and Has Two Kids to Support”

I have been reading your letters for months and I appreciate and admire how much you’ve helped people and I hope you can help me. I am 23 years old and live with my parents and am currently in a relationship with the love of my life who is 28 and also lives with his parents. I truly adore my boyfriend, and I think he feels the same way. It’s just that his life is sort of a mess right now. He has two children with two different women, one of whom has passed away. He loves his kids very much, but he doesn’t have enough money to support them. He and…

“I Feel Like My Boyfriend’s Sibling”

I’m nearly 25 and have been with my partner, Greg, eight years now on and off (mostly on). Last November, we moved into his parents’ annex, which is classed as different properties but has the same private landlord. At first, I thought it was a brilliant idea — we could have our own space, get a dog and really begin our lives together. However, things have not gone as I was hoping. Not one single day or night passes that Greg doesn’t need to go “next door.” I work till 7 or 8 some days and all I want to do is sit down, have a glass of wine, and talk with…

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