Your Boss’s Baby News Isn’t Harassment—It’s Biology

“Holly, so I’ve worked at my company for 5 years. My boss has been pregnant twice in that time. Not sure why, maybe because I’m Gen Z and we get offended by everything, but I feel when your boss says ‘I’m pregnant,’ that’s basically sexual harassment. Like now I have to think about how that […]

Your Dad’s Dating Your Classmate—Yeah, It’s Weird

“Help me Holly!! I just don’t know what to do. A girl I’ve known since 11th grade (we’re both 25 now) is dating my dad (who is 45). I know he’s considered handsome, stays in shape, and has some wealth, but it’s so weird seeing her at his house. This girl was at my high […]

What Happened in Vegas Came Home With You

“Holly, I went on a girls’ trip to Vegas. My boyfriend was against it. Said Vegas is no place for a woman about to be married. Of course, I said I’m a grown woman and he should trust me. After giving me the guilt trip, he relented and I went to Vegas. Ugh! I screwed […]

Sick Days Aren’t a Guilt Trip

“Hello Holly, my boss always asks me to work an extra shift after I call off sick. I’m scheduled 40 hours, but if I only work 32, he tells me I should pick up a shift to hit my 40, even though I’m using PTO to get paid for 40. If I decline, he gets […]

Put Down the Controller, Pick Up the Ring

Seven Years, a Controller, and No Ring “Dear Holly, my boyfriend refuses to propose. We’ve been together seven years. I’m 30, no kids, and he’s still playing video games. He has a good job but spends all his free time with his controller and his buddies. Am I wasting my life away?” Oh, sweetheart. You’re […]

The Peeping Perch Next Door

“Hi Holly, what should I do about a male neighbor that always goes out on his 2nd floor deck while I’m sunbathing next to my pool? I look several times a day, he’s never on that deck. The minute I go out there in my swimsuit, he is sitting up there, eyes all over me. […]