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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 Second Chance? who wondered whether she should reunite with a boyfriend who had a hard time closing the door on prior relationships, including with an ex-wife and another ex-girlfriend. Her update is below.

Two months ago I sent inappropriate pictures to one of my boyfriend’s friends while on vacation. Since then, I realized it was a huge mistake. I have grown as a person and will never do something like that again. My boyfriend has said to me in the past that he will end things with me if he finds I have cheated. I do not want to tell him, but some part of me feels the need to. I need help. — Inappropriate

I am 41 years old and dating a guy, “Brad,” whom I have known since elementary school. Brad has always been a great friend, and we have maintained contact over the past 20 years. Last June we started hanging out. Well, we ended up becoming friends with benefits because Brad, who has been a bachelor for 20 years, has an active and very busy lifestyle. I fell in love with him during the course of all this and he expressed he wasn’t sure he could do a relationship after being single so long. So I decided to continue with how things were despite wanting more. In February, my living situation became unbearable….

I’ve got three letters for you today: I met a guy, “Robert,” who I have fallen head-over-heels for. He is in a long-distance open relationship with a girl, “Rachel,” whom he has not seen in over eight months. He and I just started doing things together like hiking and going to the movies, and one day I realized I was in love with him; he admitted he was in love with me, too. I told him that I do not do open relationships and that I can be quite needy. He informed me that all his previous relationships had been closed and he got hurt in his last one, leading to his…

My significant other of seven years, “Chris,” allegedly touched a female acquaintance – “Jericho” — whom I’m in a weekly driving class with. I’m 45, Chris is 49, and Jericho is 30. Jericho needed a ride from class because she and her boyfriend had broken up. We gave her a ride to her friend’s after class. The following week she had rented a room at a local motel — because she and her boyfriend are fighting/going separate ways — and wanted a ride after class. I agreed; however, I had to go to a store in an adjoining town to pick up my order. I left her in the vehicle with my…

I just moved in with my boyfriend, “Greg,” after dating seven months. He and his ex were together five years, and when they met, she had a six-month-old daughter, “Lucy.” Her dad is completely out of the picture so Greg assumed the role as dad and bonded with Lucy even closer than with his biological daughter who’s around the same age, whom he shares with his ex-wife and gets every other weekend. He explained early on that he intended to remain Lucy’s father and to get her on the same weekends as his bio daughter, and I meditated on it and decided I could open my heart to this. His ex quickly…

A few days ago I commited the ultimate sin: I vented on Facebook about how very little housework my spouse, “Clark,” does and how unfair this feels to me. I hadn’t been sleeping well, and he had. I was also in a lot of pain. I am not making excuses — just giving a bit of background that led up to the “incident.” Everything combined into the perfect storm and I blew up. I know I should not have done so on social media. Immediately, Clark’s sister came promptly to his defense and ripped on me like never before. I have since appologized to her and told her she was right to…

In February, the daughter I gave up for adoption almost fifty years ago, when I was only fifteen, found me through DNA testing. I’ve always thought that my boyfriend at the time was her biological father. I’ve only just come to find out that her conception was the result of a sexual assault. All this time I thought one thing and it turned out to be something else. She withheld her father’s identity from me until after I poured my heart out about my situation and boyfriend at that time. It was very difficult and somewhat traumatic for me. She has been emailing and texting my two children, and they seem to…

My little person is seven. I spent the first three and a half years of his life and on off with his biological father, “Chuck,” before I realized enough was enough and it was healthier for us to part. I spent the next year and a half mostly single but ultimately started seeing a good friend of mine, who is my now-fiance, right around my son’s fifth birthday. I don’t feel the need to go into detail here — it’s wonderful and he loves us both, but my issue is co-parenting with Chuck. About nine months ago Chuck popped in and decided that since he — at 27 years old — had…