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My boyfriend, “Stan,” and I have been together for about six years and met while I was still a teenager. Not too long ago we broke up but then got back together pretty quickly. I initiated the breakup because I felt that I was allowing the relationship to hold me back from social and academic opportunities. We got back together because we felt that we could encourage each other to pursue other things while still in the relationship. First breakup aside, I am noticing some things about the relationship that make me feel unsure about our ability to stay together in the long run. We have very different political and world views….

The father of my children and I have been together for a few years. We live together, share a life, and are planning a future. We want at least one more child, a house, and marriage. Here lies the problem: He’s still in contact with his ex and taking care of her daughter (he says it’s strictly for HER daughter). He says he’s been around the daughter since she was three, they broke up when she was five. She’s eight now. I didn’t know he was financially/physically taking care of the child until now. The mother calls whenever she needs money. She calls over and over. She writes inappropriate comments on his…

New readers, welcome to Dear Wendy, a relationship advice blog. Read some of the most popular Dear Wendy posts here. If you don’t find the info you need in this column, please visit the Dear Wendy archives or the forums (you can even start your own thread), do a search in the search bar, or submit a question for advice at wendy(AT)dearwendy.com. I read the column, “My Husband and I Can’t Agree on Where to Move”, as it’s applicable to my situation. My wife and I live in the San Francisco Bay area. My daughter and family live less than 45 minutes away (driving time), with the rest of wife’s family about…

From the forums: My boyfriend, “Fred,” and I have been together for over four years. During our first three years together, Fred and his sister were not speaking due to a fight they’d had a year before we got together. I only met her a year ago and she was very cold to me. He’s not close with her, but they text every now and then. She’s very close with his ex, whom she knew during the eleven years the ex and Fred were married. His ex hates me and has threatened to physically attack me if she ever sees me in person, which makes coordinating holidays very difficult as they have…

My sister, who is six years older, had a child immediately after high school and was left as a single mom (I was 13-ish). She had plenty of help from my parents, grandparents, middle sister, and the dad’s parents. She was helped financially with life and school. My father bought a duplex for her to live in, which she has been trying to buy from him ever since (nineteen years now). Six years ago she had another daughter, yet again with a dead beat dad; however, the landscape has changed and I’m sorry to say the first child (now 18) had a lot of responsibility in helping take care of the new…

​​It’s time again for Shortcuts. For every question, I’ll give my advice in just a few sentences because sometimes the answer to a person’s question is so obvious and the need to hear it so great that being as clear and frank as possible is simply the best way to go. My boyfriend and I have been living in our first apartment for nine months and it’s been really hard. A couple of times I had to pay rent myself because his job was cutting his hours. Neither of us has a car and I’m the one always paying for ubers. He has always been a little irresponsible with his money — spending…

Last weekend my girlfriend, with whom I own a house and have lived with for about ten years, was invited to and went out on a hen night locally. For her this meant getting ready early and out the door by about 6 pm and returning home in the early hours. That’s fine and I am sure she had a good time. However, there was also a wedding which had presumably been planned for a year or more and that my girlfriend had obviously received an invitation for some considerable time before, and she suddenly tells me that the invitation didn’t include me. I’m not sure I believe I wasn’t invited, and…

I have two small children, a boy and a girl, and I reunited with an old classmate of mine a couple months ago. He expressed his feelings for me, he took me to meet his parents, and they enjoyed my company, but there’s a problem. He is currently doing a two-year stint in jail for something he did when be was young. He takes full responsibility for what he has done. I honest to God love this man with all my heart and he loves me just as much, but I’m scared that he might get released and then move on from me. Should I leave him alone or should I hold…

I am a divorced mother of three. My ex was abusive and cheated on me many times. I have been dating “John” for three years now. He is a single father of one. His marriage broke up because his ex-wife ran off with one of his best friends. We’ve recently moved in together. We live in Canada in an area where lap dances are all-touch with few exceptions. There are many strip clubs that offer other “services” at the right price, too. A few months ago John went out with the boys. Before he left, he was very loving and affectionate, saying things like he couldn’t wait to get home later so…