National Boyfriend Day takes place on Friday, October 3, 2025. While the day of the week changes each year, you can look forward to National Boyfriend Day taking place on this day annually.

I really need help. I’m a 28-year-old woman living in New York City. For the past three years, I’ve been in a committed relationship with my boyfriend, “Charles.” He’s 31, works in tech and is super ...

From Shakepear's words to modern-day trends, we have picked some of the best lines you can send your boyfriend.

Dear Eric: I’ve been dating my boyfriend for roughly two years. We took a break because he hadn’t told his grown daughters he was dating. I asked that he do that for us to move forward in our ...

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 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 ...