Category: Ask Anna

Dear Anna, I’ve been dating my boyfriend (36M) for five months, and recently, I found out that he had quite a reputation for sending unsolicited, borderline harassy messages to women online.

Dear Anna, I’m a 40-year-old newly divorced career gal, and dipping my toes back into the dating pool after a long marriage. I’m not looking for anything super serious just yet, but I also don’t want to waste time on people who aren’t genuinely interested or who have wildly different values or goals than I do.

Dear Anna, I’m a 41-year-old woman, just getting back into dating after an eight-year relationship, which ended a little over a year ago. In the past, I’ve spent so much energy looking out for red flags that I realize I’ve never really paid attention to the good signs — the green flags.

Dear Anna, I’m a 27-year-old woman, and my boyfriend (31) has always been passionate about political activism. I admire his dedication to causes like climate change and social justice, but lately it feels like our relationship is getting lost in the shuffle.

Dear Anna, We’re serious — and lately are talking more and more about marriage. But something from my past has been weighing on me, and I’m struggling with whether or not I should tell him.

Dear Anna, are we too isolated, or are we just fine the way we are?

Dear Anna, before moving in, we used to have sex several times a week, but now it’s once a week, or maybe twice if it’s, like, a special occasion.

Dear Anna, I love her deeply, but I’ve noticed that she’s always on her phone — whether we’re watching TV, having dinner or just hanging out in bed.

In a healthy marriage, both partners work together to ensure the other feels loved, respected and secure, writes Anna. That’s not too much to ask.

Dear Anna, my boyfriend made a comment that’s really stuck with me. He mentioned that he doesn’t find my work-from-home outfits “attractive.” It caught me off guard and, to be honest, it’s made me feel a little insecure.