Amy Alkon

I’m a man who likes to girl-watch. I do this from behind very dark glasses, yet I still elicit scowls from women. Recently, I was at a help desk, and I availed myself of the view down the receptionist’s top. She quickly covered up with a scarf. I’m puzzled, because there’s no way she could’ve […]

PHOTO COURTESY AMY ALKON Amy Alkon I’m a 35-year-old woman, and my boyfriend of a year is 43. Sadly, my friends and family don’t like him. They think he’s “not good enough” for me. Their argument: He doesn’t have a full-time job with benefits (like me), plus he smokes pot to relax; therefore, he is […]

PHOTO COURTESY AMY ALKON Amy Alkon I dragged my boyfriend into the makeup store Sephora, and he said, “Save your money. You don’t need any of this stuff. I like you better without makeup.” Huh? Why is there a huge makeup industry when so many men say they don’t even like makeup? – Pretty Confused […]

PHOTO COURTESY AMY ALKON Amy Alkon My boyfriend and I have been together for a year and a half, and we really love each other. His parents adore me and are thrilled that he might not die alone. After his mom saw us being all cuddly in the supermarket, she warned him that we may […]

PHOTO COURTESY AMY ALKON Amy Alkon I’m a woman in my late 20s. Guys don’t have car crashes looking at me, but I am pretty and have a nice boyfriend. I have three drop-dead gorgeous girlfriends who are perpetually single, but not by choice. I realized that they all do two things: complain that things […]

PHOTO COURTESY AMY ALKON Amy Alkon When I was in my 20s watching “Sex and the City,” I saw the Samantha Jones character as a sexual role model – thinking I could have love-‘em-and-leave-‘em sex like her. However, even when I only wanted sex, I always had a sense of loss when one-nighters didn’t evolve […]

PHOTO COURTESY AMY ALKON Amy Alkon I dress like a tomboy: jeans, T-shirts, hoodies and work boots. My boyfriend of a year wants me to wear skirts and dresses more often. Nothing trashy. Just not my usual tomboy wear. This weekend I wore a sundress to brunch. It made him so happy, and he kept […]

PHOTO COURTESY AMY ALKON Amy Alkon I’m a Harvard-educated man in my late 30s. I’ve had many ugly arguments with girlfriends, probably because I am highly opinionated and won’t give in when I’m right. I’ve always dated smart, professional women around my age but I’m now dating a 21-year-old girl, and I’m thinking this could be […]

PHOTO COURTESY AMY ALKON Amy Alkon Four months ago, I started hooking up with this hot guy I met on Tinder. He isn’t someone I’d normally go for; he’s a total mess and serious trouble. He always made me come to his place and I always left feeling gross rather than satisfied. However, about once […]

PHOTO COURTESY AMY ALKON Amy Alkon A female friend overheard me on the phone with my boyfriend and became concerned. He and I tease each other relentlessly, calling each other mean silly names, but it’s all in fun. Though we have a very loving relationship, she thinks the teasing is a sign of submerged anger. […]

PHOTO COURTESY AMY ALKON Amy Alkon I’m a single guy who started a “friends with benefits” thing two months ago with an unhappily married female co-worker. We’ve since developed feelings for each other and started talking about a future. I’m worried because people always say, “If she cheated with you, she’ll cheat on you.” And […]

PHOTO COURTESY AMY ALKON Amy Alkon I’ve always been a very athletic guy. I do jujitsu every day. When I don’t exercise, I feel depressed. My girlfriend, however, has never been very physically active. She has a great body – naturally slim – without doing anything, which is probably why she’s unmotivated to work out. […]