Dear Annie: I’ve been dating my boyfriend, “Dylan,” for almost two years. He’s perfect except for the fact that he avoids conflict like the plague. If I bring up anything even slightly uncomfortable — ...

DEAR ANNIE: I recently had my 50th birthday. My boyfriend and I have been dating for seven years, with a two-year break. His friend recently asked me if my boyfriend gave me a present from him. I hadn ...

Dear Annie: I recently had my 50th birthday. My boyfriend and I have been dating for seven years, with a two-year break. His friend recently asked me if my boyfriend gave me a present from him. I hadn ...

Dear Annie: My boyfriend and I have been together for eight years. We have an 18-year age gap. I’m 39, and he’s 57. We have a strong relationship and have been through hell and back together. God ...

Dear Eric: I have two children from a previous relationship, and I am in a new relationship of five years. My 11-year-old son isn’t the most masculine fella or sporty fella, and he has trouble making ...

Note: This column originally ran in 2022. Dear Annie: I recently had my 50th birthday. My boyfriend and I have been dating for seven years, with a two-year break. His friend recently asked me if my ...

DEAR ERIC: My boyfriend and I are in our early 80s. I am divorced and his wife died over two and a half years ago; we have been dating slightly more than a year. We do not plan to marry, but we are in ...

My boyfriend will be moving in with me in two months into my home which I own. He plans to pay $1,000/month in rent to me, which is slightly more than what he currently pays, until he pays off his ...