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I am a male in my late 50s and have been dating, for just under two years, a lady, “Maureen,” who’s a couple years younger than I am. She is a busy executive and has a 17-year-old son at home who is her priority; therefore, we have limited time together. I realized a few year ago that I have an “anxious attachment style” which I have been making progress on with a therapist, but I still get triggered. Maureen’s ex-husband cheated on her and had a child with the girlfriend. Maureen has worked for almost ten years to get herself back. She tells me all the time that she does not want…

I am engaged to my former high school boyfriend, “Alex.” We reconnected after 30 years, and now, a year later, we are engaged and living together, planning our wedding. My issue is this: When Alex and his ex-wife split up, she had a boyfriend and Alex had a semi-girlfriend – a rebound girlfriend. This rebound was actually living on the property Alex shared with his ex-wife, and was a friend of his wife’s, and the ex-wife actually encouraged it because she already had a new boyfriend. When Alex and I reconnected and became exclusive, I was told he’d had zero contact with the rebound woman for eight months, but that turned out…

I’m a 29-year-old lesbian who has been out for 12 years, dating my 43-year-girlfriend a little over a year, and living with her for seven months. She has three boys (20,12,6) and only the eldest knows we’re a couple. (Even then, it took her about three months after I moved in to tell him.) I’m the first woman she has seriously dated and she refuses to tell her youngest two that we are together, although they see me sleeping in the same bed with her and hear me calling her “babe.” It’s starting to take an emotional toll on me. She has sought the advice of older cousins (also lesbian) and taken…

I’m dating someone, “Ryan,” who was in a relationship for seven months with someone I knew. She had a son and a daughter. He pursued me after they had broken up which, from my understanding, was her idea. Since then, she found out he was talking to me and immediately got hateful. She and I were never buddy-buddy; she only watched my son for a little while, but she says I’ve betrayed her. Well, Ryan said he understands her reasoning, which doesn’t make sense to me. Also, apparently while they dated for seven months, Ryan grew attached to her daughter, “Allison.” Allison apparently wanted him in her life and calls him her…

My husband, “Joe,” and I have 2-1/2-year-old. Joe has changed her diaper twice – both times in the hospital. He has never bathed her or prepared her a meal, and he has only put her to bed a handful of times, after I’ve asked. He also does not do housework at all unless I get upset. This is not the main problem though. We run a pub; it is leased in both our names. Obviously, with the pandemic, we have been told to close. Before this, we were on the back foot financially and have racked up a bit of debt. I worry because we borrowed from my sister and brother whom…

I’m 48 and dating after leaving my marriage in September 2018. After a year-plus of one-night stands and hookups and situationships, in January of this year, I finally met a guy, “Carl,” 51, whom I really like. He shows up. He’s attentive and kind. We have a lot in common and I very much enjoy the time we spend together. He’s pursued me and just this weekend told me that he loves me. He wants to date exclusively and I’m on the fence. I can’t decide if my fear is of intimacy (working on this in therapy), fear of missing out (on dating other guys), or red flags. My question is about…

Hi, DW community. We are starting this week in what feels like a whole new world. Here in NYC, schools are closed for at least the next five weeks (and possibly through the end of the school year) with online classes set to begin next week. Bars and restaurants are closing for everything but take-out and delivery, and everyone is encouraged to stay home and put all in-person social interactions on hold for the forseeable future. (These /measures are painful – especially for those whose income and businesses will be so dramatically affected and for the many children who depend on school for a myriad of social services- but I agree that…

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 “Assessing The Risk” who was unsure whether or not to respect her husband’s wishes that she not take her 6-year-old child on vacation to Florida amid the coronavirus outbreak. Her update below.

I have been in a relationship with my boyfriend, “Jason,” for nearly seven years. I am a single mother, and we started dating when my son was one. We live together and I would classify us as a family unit despite our not being married. I own the house we live in so we are not constricted by a lease, but if he were to move out, my bills would double and I would also have no support system in regards to back up with my son if I am at work or want to go out or have any kind of life. Over the years we have had a wild sexual…