Savage Love

Dear Dan: Last summer, I reconnected with a high-school teacher I hadn’t seen for a year. We first met when I was 15, and I had nothing but respect for him and his intelligence. I also had a crush on him for the next four years. Fast-forward a year. He is sexting me ...

Dear Dan: I’m a gay man in my late 20s, and I can’t get fucked. I have tried to train my ass, but the largest thing I can place inside remains a small butt plug. If I try anything bigger, the pain is unbearable. I’ve always been a very anxious person, and it’s clear ...

Dear Dan: I’ve talked to my girlfriends, my mom and his mom, but I need some unbiased advice. I’m a 28-year-old woman in a relationship for three-and-a-half years with a wonderful man, also 28...

Dear Dan: I’ve got a question I doubt you’ve ever gotten before. It has a bit of everything: sex-work etiquette, long-distance phone interaction, and a het cis chick anxious not to lose her tolerance badge. Here it goes: A few months ago, I started getting hang-up ...

Dear Dan: I am a man who tends to ejaculate prematurely. Not all the time — but at least 50 percent of the time, I’m good for two to three minutes and then I REALLY have to be careful. I’ve learned to manage it and work around it (like, stop if I’m too close and eat ...

Dear Dan: I am a 22-year-old bisexual female, and I have a boyfriend who I love. He says he wouldn’t mind if I hooked up with other girls, as long as it was a onenight thing. That’s not what I want...

Dear Dan: I am a young gay man who has been so freaked out by the idea of catching an STI that I haven’t gotten with anyone for two years. But last night, I hooked up with a cute 21-year-old FTM trans boy, and maybe because it was a person with lady parts, I let ...

Dear Dan: Here’s the Reader’s Digest Condensed Version: I’m a sexually inactive (by my own choice) heterosexual female in my late 40s who up until recently used to be much heavier and in rapidly declining health. Since my type 2 diabetes diagnosis, I have achieved ...

Dear Dan: A big congrats to Caitlyn Jenner on her big reveal and lovely Vanity Fair cover! But I am having a crisis of conscience. On one hand, I support a person’s right to be whoever the heck they want to be. You want to wear women’s clothing and use makeup and ...

Dear Dan: We have a new shorthand term for BDSM doms who are abusive assholes: Ghomeshi doms. Good guys into BDSM should stick this in their online profiles: “I’m a nice, non-Ghomeshi dom looking for a lady who is into...

My boyfriend of three months, “Marcus,” told me last week that he is a trans man. He’s performed oral sex on me and fingered me, but he never let me reciprocate and told me he didn’t want to have penis-in-vagina sex yet because that was a large commitment. We go to ...

Dear Dan: Yesterday, I found my 5-year-old son putting things up his butt in the bath. This isn’t the first time — and it’s not just a “Hey! There’s a hole here! Let’s put things in there!” kind of thing. The little dude was rocking quite the stiffy while he did it. ...