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My boyfriend and I have been living together for the past year, and we recently traveled out of state to attend my oldest sibling’s wedding. My parents always pay for my youngest sibling’s airfare because she is still college-aged and needs the help. In an attempt to be fair, my parents paid for my airfare to the wedding too. While I didn’t consider their help to be a secret, I also didn’t mention this fact to my boyfriend until it came up in conversation last night. I had booked our flights at the same time using my parent’s credit card, and, when he gave me the money for his flight, I passed…

My fiancé and I have been together for just over three years. I’m 29, and he is 37. We have both been married previously. I have one son from my previous marriage; he has no children. My ex-husband and I are very civil towards each other, and, for the most part, get along fairly well. Problem #1: My son is 7 and although he and my fiancé mostly get along well, there are times when they will argue about useless stuff. My son is very bright, and he likes to over-explain things to make sure people understand what he’s talking about. My fiancé takes that as arguing, so he gets mad. Example:…

I have been dating my girlfriend for a year and a half. I am 47, divorced, no kids. She is 46, divorced, with a 6-year-old daughter. I am into fitness and am physically fit, and she is about 50 pounds overweight. Having such a young child and being so overweight were two things right from the beginning that I knew would bother me. But she is a wonderful woman and has such a big heart, and she treats me well. I decided to look at the big picture and see if I could look past her weight and the challenges that come with dating someone having a little kid. Since we always…

New readers, welcome to Dear Wendy, a relationship advice blog. 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), or submit a question for advice. 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 boyfriend and I have been together for four years and have discussed marriage soon. I love his family to death, but there are some ‘boundary’ issues…”

My husband and I are planning to start trying for a baby in a few months. We are super excited and super ready and are just waiting for the right time in my career (i.e. my being eligible for maternity leave). Who knows if and when we’ll be successful, but I want to know how and when I should tell my so-far infertile older sister. My sister, 5+ years older and married two years longer than us, has been trying with her husband for about three years with no success. From what I hear, specialty doctors suggest there’s practically no chance she can bear a child and probably needs either a surrogate…

I’m 49 and recently divorced after a 21-year marriage. I’ve become involved with a 48-year-man whom I adore and have fallen in love with. We’re amazing together and this is the most fun I have ever had with a man. I was separated for two years before my divorce, during which time I dated different men but never clicked with any of them — not like I do with this one. He lives an hour away and we have been spending every weekend with each other for the last five months and it’s been great. We have even talked about getting married! He also was married for 16 years and has been…