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I am legally separated from my husband, in the process of getting divorced, and have a 4-year-old who is everything to me. In no way was I looking for a relationship yet, nor to introduce anyone to my son for a while. This guy I knew from growing up — “John” — and I dated a bit when we were younger, but I hadn’t seen or spoken to him in ten years. He recently reached out to me while he was away at training for two weeks and very quickly he was talking about how he’s always been in love with me and now that I’m almost divorced he wants to be…

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 husband and I are celebrating our ten years of marriage by having a dinner party at a nice winery with close friends and family. The only thing is that we cannot afford to pay for everyone’s plate at $60 per plate. We never had a wedding; we got married at 18 and want to do something really nice now. Is…

I’ve been with my boyfriend, “Frank,” for four years now. We’re both divorced from previous marriages and have kids with our exs. In addition, Frank has a step-daughter, “Grace,” with his ex. He helped raise Grace from infancy until she was about 8 years old. And then Frank divorced Grace’s mother due to her cheating on him. Well, it’s been four years and I haven’t spent much time with Grace. She spent a summer with us early on and she and I were driving to the store together alone when a conversation about boys and crushes and kissing came up. I asked Grace if her mom had had the sex talk with…

I’m 32, and have never had a boyfriend. I lead a somewhat structured life because I have mild to moderate OCD. If I clean the toilet, I have to shower for 15 minutes afterward. If I wash my clothes, I have to write in a notebook which items were washed. I sometimes keep diaries about important conversations I have with friends/people so I can refer back to. If I hold someone else’s baby, I sometimes feel compelled to wash my clothes. If a diaper is changed on furniture, I won’t sit there until it’s cleaned/washed. I prefer not to use public bathrooms unless I’m really desperate. The times I’ve had sex, I…

I’ve been married for ten years, and I have a pretty open and good relationship with my husband, “Ted.” He supports everything I can do to feel better since car accidents have rendered me in constant pain. Plus, I have PTSD, depression, and anxiety, and I have had a lifetime of therapy. I’m 56. I have had five surgeries including, most recently, a lumbar spinal cord stimulator implant, and I’ve now started on NJ’s medical marijuana program through my pain doctor. Even though my husband understands the benefits and is not concerned with the legality or expense, he gets pissed off over smelling it even when I use filters like smoke buddy,…

My boyfriend and I have been dating for eight months. We love each other very much, our connection is very strong, and we are very happy together. We have talked about a future together, getting married and having kids. The problem is: He does not seem interested in getting to know my 2-year-old daughter from my previous relationship. He met her once before and everything went well, but then one day I brought her over to his house so they could get used to each other and my daughter was a little shy the entire time, which is understandable. He then copped an attitude, but he wouldn’t tell me why he was…

It’s time again for “Dear Wendy Updates,” a feature where people I’ve given advice to in the past let us know whether they followed the advice and how they’re doing now. Today we hear from “Dating Grief” who wrote in over five years ago with a question about her new relationship. Her boyfriend of three months had just lost his father and was withdrawing from her emotionally. The relationship was so new that she didn’t know whether to attribute his behavior to grief or to his not being into her anymore. Five years later she has an update and another request for advice:

My ex and I never really broke up. We have an 18-year-old child together, but his parents never liked me. About five years ago, he walked out of my life and started dating a woman he doesn’t love. The reason I know this is because two weekends ago we met for coffee and he told me they fight all the time and the reason he is still there has to do with money. His name was put on the deed of her home to help krrp it from foreclosing. He also said he wants out but doesn’t want to move back with his mom. I completely understand! That day we spent together…

I am 20 years old and my boyfriend is 21. We are graduating college in about two months, and we have been dating for a year. He has been looking for a job in banking, and I told him my dream is to move to Colorado and attend Boulder Law next year (I will devote to internships and studying for my LSAT in the meantime). He worked extremely hard to apply to jobs there, and we found out last week that he got an excellent position in Denver, Colorado. It feels as if my dreams are coming true. We decided that we should share an apartment next year while he works and…