Amy Alkon

On Crowd Nine I’m a 43-year-old woman in my second marriage with a man who’s also on his second marriage. We are both determined to make this marriage our last! We have a scheduled date night. We make sure sex happens weekly. I’d like to know whether there are other things we can do to […]

Bare Tracks My boyfriend asked me for nude photos of myself. I reluctantly sent him one. I feel very uncomfortable about sending it, and I don’t want to send more — though sending naked pics now seems very common. Am I paranoid? —Online Privacy Fan Unfortunately, “online privacy” is one of the more absurdo oxymorons—a […]

Venus Envy I got a boob job two years ago. My best friend, seeing the results, wanted one, too. When she realized she couldn’t afford it, she started making snide comments about women who get them. Recently, a guy was hitting on me at a party, and she started flirting with him and asked, “Do […]

Foresee Sick I’m good friends with an ex. She’s a great person, but we just don’t work romantically. For two years, I’ve been seeing a woman I love and want a future with. She initially said she was fine with my friendship with my ex. Two months ago, she said she was uncomfortable with it […]

Sorry, Wrong Num-Num I love my boyfriend. We’ve been together two years. Recently, however, we’ve been experiencing conflict over the issue of children. He wants kids; I don’t. I’ve always felt strongly about this, and he said he was fine with this when we started dating. But he’s been bringing up the subject of kids […]

Bedder Later I’m a woman in my 20s seeking a boyfriend. On the first date, I like to have a few drinks and, if the guy and I hit it off, have sex to see whether we have physical chemistry. Lately, I’ve had a string of great first dates — flowing conversation, emotional rapport, and […]

The Fastidious And The Furious I’m a divorced guy in my 40s. I was at a bar with friends and went over to talk with a woman I found really attractive. Though she wasn’t the friendliest, I asked to take her to dinner. She said she’d think about it and then asked for my Instagram. […]

When Hurry Met Sally I’m a guy in my 30s. I thought I’d found the love of my life. We had an incredible first few dates. We were so in sync we didn’t even need words to communicate. However, as we’ve spent more time together, things about her are really starting to bother me — […]

The Camera Sutra I really like the girl I’m dating, except for one thing. On every date, she asks me to take photos of her for Instagram. Afterward, she consults me repeatedly on which will “get the most likes.” I’m starting to get really annoyed, and I find it cuts into my enjoyment of our […]

Disappear Pressure I recently met this guy, and we’ve spent the entire past week together. Unfortunately, he’s moving across the country—tomorrow. He asked whether I’d be open to dating after he moved. I panicked and said no—I’m really not looking for long-distance—but now that he’s leaving, I’m sad, and I’m worried I’ve made a mistake. […]