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I know you must get a ton of questions, so I’ll go straight to the point. My boyfriend is 34 and I’m 22. It’s the first serious relationship I’ve ever been in, and we’ve connected on many levels after I decided I would give him a chance. Reasons I went for it: – He has a great personality – He’s very sociable – He’s kind – We have things in common – He’s smart – He loves me a lot Reasons I was so f***ing hesitant: – Age gap – His looks (I’m talking maaaybe a 6 out of 10) – Our height difference (I’m 5’10”, he’s 5’8″) I’m absolutely aware those…

I have been with the father of our two amazing children for 21 years and engaged for almost 20 of those years. We have had our ups and downs. I have always been the one who feels unworthy of him, and even more so now. He is my world; he has been since the day I met him. And yet, he never mentions getting married. Maybe twice in all these years. He blames me for arguments we have had in the past in which I have taken off my rings because I wonder why I wear them if he won’t even talk about marriage. I’m going to be 45 next week and…

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’ve lived with my two guy friends for about two and a half years. They’re my best friends in the world, and although we argue and fight sometimes, they’re still my family. We’ve supported each other through everything from broken hearts, to getting fired, to the loss of a parent….

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. In nearly six years, my boyfriend, Bryan, has paid rent one time and has never ever paid a full month’s bills. He has had multiple jobs and just finally got back to work in May after being off for two years. We are in July now and he has paid me a total of $500 that he won at the casino….

I wrote to you once before after a traumatic stillbirth that I experienced over a year ago, and you sent a private response. Your advice and compassion helped me through a very difficult time. Now I’m currently 21 weeks pregnant with a little girl, and things seem to be going very well, except for one thing: I need my mom and she isn’t here. My mom passed away when my son was three and a half months old. He will be 13 in September. Now that I know I’m having a little girl, I feel lost. My mom was my everything, and, even with her being severely ill for 20 years, she…

I chose to be single for about three years because I was just so tired of dealing with men/relationship issues (cheating, lying, drama, etc.). I’m divorced because my ex-husband had an affair and I’ve had awful relationships since, but I have been with a great guy for nine months now. We’ve known each other for about 17 years, but we were always just friends until this past October. Everything is perfect except for his terrible ex (whom he has an 8-year-old son with) who still controls his life and tries to make him miserable any chance she can because she is miserable. She uses their son as a pawn, and it is…

My girlfriend and I moved into our first place together. We’re both in our late 20s and work as nurses at a local hospital not too far away. In our home, right off the garage is a mud/laundry room. Our normal routine after we get home from work is to shuck our scrubs right into the laundry so the crud from work doesn’t track in. I recently threw a surprise birthday party for her. We all heard the garage door and took our quiet hiding places. During that delay, it started to occur to me that she was probably stripping down like usual in the laundry room, something I just didn’t think…

I dated “Craig” ten years ago. Things went horribly wrong between us when I found out he was addicted to crack. I never did that with him nor did I want to. He put me in some pretty awful situations, Children’s Aid was called, he stole money from me, he stole gas; he was an addict and would do anything to get crack. I know it’s weird to say but he was the love of my life and always has been. I have never felt the way I felt about him with anyone else, including in the seven-year relationship I have just recently gotten out of. I lost touch with Craig for…

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 “I Just Want A New Job” who graduated from college last May, was working in a temporary entry-level position, and had been looking for a new job for months while starting to feel a lot of anxiety about how long the process was taking: “I’ve had several interviews which haven’t worked out (and plenty of non-responses to CVs, which I actually find easier to deal with), and it’s taking a toll on my self-esteem. Objectively, I know…

My daughter was born with feet and ankles that are bigger than normal. Except for this defect, she is very well-structured, with medium height and slim weight. She is 25 years old, working for a prestigious IT company as a junior programmer. When she was younger, she dreamt of getting married. However, she has been disappointed once or twice, and I can see from her face that she has lost self-confidence and I think she is depressed. Unfortunately, she associates those disappointments with her defect. I have been encouraging her to focus on what she is good at (she can sing) and that people will follow suit and focus on that rather…