Maybe you can tell by my cheat sheet (pun intended), but before the night in question happened, my head was all over the place. And it all came to the surface on Valentine’s Day; My boyfriend (“Tom”) ...

I’m a 34-year-old woman who’s been in a relationship with my boyfriend for almost four years. We’re serious — and lately are talking more and more about marriage. But something from my past has been ...

Dear Readers: To mark my final week writing this column, I’m re-running some memorable Q&As. Dear Amy: I am in the most loving relationship with the man I want to marry. We talk about marriage often.

Dear Amy: I am a middle-aged single woman and recently started seeing a man my age. I was married for 20 years, and he has never been married. My two children are in college. He is a really sweet, ...

This column originally ran in 2021. Dear Annie: I am in my late 60s, and my boyfriend, “Mark,” is in his early 70s. We have been living together in my house for a year and a half. We’re both divorced ...

Kai has been with her boyfriend for nearly a year but hasn’t told her parents out of fear they’ll reject him. Amy and T.J. think it’s time to rip off the Band-Aid. (Photo illustration: Yahoo News; ...