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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 “Just Friends with Jane,” again, the man whose girlfriend, “Eve,” requested that he stop talking to his longtime female friend from childhood, “Jane.” Jane is like his sister, he said; he talks to her on the phone every Sunday and occasionally sees a new superhero movie with her (which Eve is invited to as well). “Eve says that I’m disrespecting her by continuing to associate with Jane and that she feels like an outsider when the three…

My daughter’s dad, “Rick,” and I haven’t been together in almost thirty years. Our daughter is now 28. Well, after all these years, Rick wants to get back together, saying he loves me and regrets leaving me, blah, blah, blah. I told him I didn’t want a relationship. I’ve been single for eight years by choice. He’s been married twice and had a girlfriend in between. He lives three and half hours away, not to mention he drinks every night. He tells me: “I know you love me, you just don’t know it.”We went out a few times together and I had a good time. But I just don’t know if I…

My boyfriend has Asperger’s Syndrome and, despite being 30 years old, has never held a job or even applied for one. I have several disabilities, but I’ve tried to hold a number of positions over the years – not always successfully, but I’ve put myself out there, even if it means I sometimes struggle or even get fired. He is on Social Security disability benefits. I understand that in order to reach a healthier place in life, some people need to go on disability benefits to make ends meet. I have empathy, given that at one point I almost went on benefits myself. My concern, however, is that he hasn’t made any…

“I am 57 and was dating a 54-year-old lady. On our ninth date we went wine tasting and dancing, and we had a fantastic day.”

My boyfriend, “Tony,” and I have been together for over six years and have been living together for almost a year. Tony was known to be quite the ladies’ man before we dated, and although I trust him 100% with my heart, I feel that he may not always tell me 100% of his plans when he hangs out with his boys. I’m 28 and my boyfriend is 33. Recently I felt the urge to look through his phone, and it seems as though a few months back he was planning to go to a hockey game with his friend but decided not to go because I was going to go as…

My boyfriend, “Levi,” and I got together fairly quickly after his separation, but his marriage was over years ago – he actually stayed as long as he did because he has a large family and they were all close with his ex. He finally realized he couldn’t stay in a bad marriage for his family, and he left. He kept telling me that his family is warm and loving and to give them some time to accept me. It’s been ten months and they still refuse to support our relationship. I’ve met Levi’s kids and they love me. But Levi’s family refuses to even meet me for coffee, or acknowledge I exist,…

As a follow-up to yesterday’s discussion, I’m curious, those of you have been engaged: How long did you date your significant other first? And how long was your engagement before the wedding? (Or, if you didn’t make it that far, how long was the engagement before it was called off?) Here’s my story:

Three quickies today: I’m a senior in high school (age 17) and my boyfriend is a sophomore in college (age 19). We’ve been dating fourteen months and are very much in love. At his college, like at most schools, there is a fair amount of underage drinking. I personally have a very strong conviction against drinking, so I have asked my boyfriend to promise he won’t drink with his friends. It would make me extremely uncomfortable if he were to drink, plus he is at school 2000 miles away and I’d be worried about his getting hurt. He says he’s happy to honor my request and he won’t drink; my question is,…