“Should I Tell My Mother I Want to Date a Guy She Tried to Put in Jail?”

I am currently 19 years old and going to college. I am moving out in five months to attend a university. My mother has paid for everything my whole life and reminds me of it every chance she gets. I work full time now, so she doesn’t pay for my food, gas or clothing. When I was 15, I was totally in love with this 18-year-old guy that my mother forbid me to see. I decided to start sneaking out to see him and ended up losing my virginity to him. Of course, my mother found out and took things to the extreme. She tried to put the guy in jail, but…

“Should I Go To His Wedding?”

For my first three years of college I had a small and incredibly tight-knit friend group. My senior year I moved in with my then girlfriend, Jill, and at the same time the group fractured. My two closest guy friends, Ron and David (who are inseparable), completely stopped talking to my girlfriend and me. We were both completely crushed and it caused a lot of sadness and anger in our house for that year. Towards the end of that year, Ron’s Mom asked me to go out with her for lunch. She had done a lot for me over the years so I felt like I had to say yes, even though…

Shortcuts: “My Boyfriend Says His Ex is ‘The Love of His Life’ “

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. 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, being as clear and frank as possible is simply the best way to go.

“He’s Posting Pictures of His New Girlfriend on Instagram”

I’m 21 and I met my boyfriend in April, 2012, and we started dating the following week. We had, like, this instant connection, so I kinda thought we would last. I live in Germany, and he is in the military and was stationed here. In March, 2013, he had to move back to the States. Saying goodbye to him was the hardest thing, and I felt as if my life were over. About four weeks after he left, I booked a flight to Colorado to see him, and I spent three weeks with him there. I later spent my entire summer break with him in Colorado again. It was perfect. Then, for…

“I’m Afraid to Tell My Parents that I’m Moving in With My Boyfriend”

I (24F) have been seeing a wonderful man (25) for a year and a half. He is everything I’ve always wanted in a partner, and I want to spend the rest of my life with him. We live on opposite sides of a large, metropolitan city, about an hour apart, he in a home he purchased a few years ago, and I in a tiny, one bedroom apartment, while I finish my graduate degree. We have discussed getting engaged, and we agree that living together before we do is important to both of us — a sort of “last box to be checked before we officially commit to spend the rest of…

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